USVI Bareboat Charter: November Sailing Yacht Adventure

USVI Bareboat Charter

Alright, batten down the hatches. This is a detailed trip report with lots of pictures from my recent USVI bareboat charter trip (oh, and we snuck in a couple days to the Spanish Virgin Islands as well).

You’ll get all the juicy details.

My original USVI sailing itinerary called for a couple crossings to and from St. Croix. However, we had to change our plans when a tropical disturbance passed nearby and veered strong winds into the SE and then the SW.

So instead, we went straight to the Spanish Virgin Islands (Culebra) on our first day, and then later spent a few extra days at St. John.

We had an absolute blast, and I love the prospects of the US Virgin Islands as a future sailing destination again (this was my first time). St. John, especially, blew me away, and we just scratched the surface. We’ll be back for sure!

Frenchtown Marina in St Thomas, where the Waypoints charter base is located
Beautiful evening at the Waypoints charter base in St. Thomas on our sleepaboard night

Arrival and Sleepaboard at Frenchtown Marina

One benefit of yacht charters in the USVI? Travel is much easier with multiple long haul flights direct from the US. In contrast, the BVI airport’s runway is too short and requires a puddle jumper or ferry connection.

After touching down, we were at the Waypoints base within 30 minutes…not bad! We opted to have our provisions delivered by VI Provisioning, despite much cheaper DIY alternatives, such as Cost.U.Less. With later flight arrivals, we paid up for the convenience factor this time.

The rest of the evening consisted of an excellent dinner at the French Quarter Bistro, stowing provisions, and prepping fishing gear for our trip to the South Drop on day 1.

Lagoon 46 in the Spanish Virgin Islands, Culebra at sunset
Our charter yacht, the Lagoon 46 at Culebra in the Spanish Virgin Islands

The charter yacht: Lagoon 46

A couple quick points about our sailing yacht, the Lagoon 46. This was my first time on the 46 but I’ve previously chartered it’s older sister, the Lagoon 450, many times. My impressions?

  • The yacht was a 2020 and in excellent shape – testament to the care provided by Waypoints (formerly CYOA)

  • Motor speed was average at around 7.5 knots and 2,500 rpms with both engines

  • She sailed great! We topped out at 10.5 knots with a following sea, 25 knots of apparent wind, and a reef in the main and jib. On average we were sailing 8-9 knots in these conditions

    • All the sheets are easily manageable from arms reach of the helm station

    • A self-tacking jib is always a plus on bareboat charter trips

  • The flybridge is our favorite hangout area, and this one had improved lounge space compared to the 450

  • Not enough storage! It seemed like we struggled to find places to stow provisions and gear

  • Our version had underwater blue lights, and those are always fun

  • Would have been great if the dinghy winch was electric

First fish of the trip, a barracuda | They love pink lures by the way

Day 1: Itinerary disruption, so off to the shelter of the Spanish Virgin Islands

In the days leading up to our trip, it became clear our plan to sail south to St. Croix was falling apart. There was increasing confidence that a tropical disturbance would pass nearby.

The result?

Strong southerly winds (25+ knots) and lots of rain. If I insisted on a deepwater crossing south in those conditions, I’m confident I would have had a mutiny aboard.

So change of plans. Where did we want to get stuck for 24-36 hours with protection from the south? I know!

Flamenco Beach in Culebra! I’ve always wanted to anchor here off a global top 10 ranked beach, and it looked like we could get at least a day to explore the area before the storm moved in.

Typically this is a day anchorage only because of it’s northerly ground swell exposure. It can also be rolly with stronger easterly trades that wrap the wind swell around into the bay.

So with our charter briefing behind us, we cranked some yacht rock, headed south, and picked up the drop for some fishing before turning west to Culebra. We quickly hooked up a few barracudas, but nothing worth keeping. Sargassum plagued our fishing endeavors most of the trip.

Carlos Rosarion reef at Culebra Spanish Virgin Islands
The reef at Carlos Rosario beach in Culebra
Our first USVI bareboat charter sunset in the Spanish Virgin Islands
Enjoying our first night's sunset at Carlos Rosario

We pre-loaded the necessary check-in info into the CBP Roam app. Once inside Ensenada Honda, we submitted our arrival. The whole process took only about 10 minutes to clear in, with a quick video chat for the one crew member didn’t have a known traveler number. With little interest in sticking around Dewey and Ensenada Honda, we went back out the channel and up the west coast of Culebra to Carlos Rosario.

After carefully checking the mooring ball (it’s a bit deep to anchor, and the bottom is coral), we decided to stay the night.

The snorkeling here is excellent, one of my favorite places. Did I mention epic sunsets over the cayos to the west?

Not bad for the first day. We celebrated with a few Caribs and Costco filets we froze and brought with us on the plane.

Our catamaran at anchor at Playa Flamenco
Our anchorage at the NE corner of Playa Flamenco

Day 2: Off to explore Culebrita and Flamenco Beach

With about 12 hours before the rain started moving in, we dropped our mooring lines and motored north around Culebra. We wanted to first check out the viability of Flamenco Beach as a 2-night overnight stop to shelter us from the approaching storm.

Trolling on the way, we reeled in a bonito, but not much else.

Bonito caught north of Culebra
Bonito we caught trolling on the shelf around Culebra

We poked into the anchorage area on the NE corner of the beach. Roll was minimal on the catamaran with winds already starting to veer into the south. With no approaching northerly swell for 48 hours, it would be a perfect place to hang out.

Before dropping the hook, we set out for a lunch stop at Culebrita, one of the prettiest beaches in all of the Virgin Islands. On our way, motoring through the channel next to Cayo Norte, we hooked, but couldn’t reel in, what looked to be a large wahoo, or perhaps a kingfish. Tough luck!

View of Culebrita from our anchorage
View of Culebrita on a quiet day as the storm approaches

There were a couple tour boats from Puerto Rico at Playa Tortuga, but they left soon after our arrival, leaving the place largely to ourselves.

We didn’t make the hike to the lighthouse this time, but settled for swimming ashore and floating in the beautiful water. And of course, we were visited by several turtles that call this bay home.

Sargassum is heavy on the west side of Flamenco Beach in the Spanish Virgin Islands
Lots of sargassum on this visit! But, only on the west side of the beach
Target practice tank at Playa Flamenco on our USVI bareboat charter trip
Hide tide at Playa Flamenco
Kiosks at Playa Flamenco where you can buy cheap Medallas
Kiosk vendors at Playa Flamenco where you can buy cheap Medallas

Back at Playa Flamenco, we took the dinghy ashore to check out the target practice tanks and grab a Medalla from the local vendors.

I’d heard of an unusually heavy year for the sargassum in the Caribbean. The west side of Playa Flamenco was the first victim that we saw on this SVI and USVI bareboat charter trip.

Wow! This was the most I had seen on a beach before, and it definitely takes away from some of the magic of this place.

Rain squalls on our USVI bareboat charter trip
We awoke to heavy squalls as the tropical disturbance moved in

Day 3: Riding out the storm at Flamenco Beach

We awoke to heavy rain squalls as the disturbance approached, and they persisted throughout much of the day. But, that didn’t stop us from fishing!

Using a sabiki rig, we hooked several bait fish. We saw a quick window in between thunderstorms, so we went out for a trolling trip around Cayo Norte.

We live baited the fish and moved slowly at around 3-4 knots. Alas, nothing memorable and we had to settle for riding out a squall before returning to our anchorage at Flamenco Beach.

Fishing in the rain at Playa Flamenco
Rain squalls couldn't stop us from fishing
Riding out a squall in the US Virgin Islands
Riding out a squall while we were fishing north of Culebra

What else to do while it was pouring? Well, we threw up the projector, set up a wifi hotspot, and streamed the World Series on the big screen.

Not a bad place to watch and celebrate the Astros win!

Watching the Astros win the World Series on the yacht on our USVI bareboat charter trip
Astros win the World Series!

Yacht Charter Day 4: The storm breaks and we sail to Magens Bay, St. Thomas

Clear skies at sunrise after the storm on our USVI bareboat charter
Sunrise departure from Playa Flamenco

We arose at sunrise and weighed anchor for a long day on the water. This was just in time as a forecasted northerly swell had just started to move in. Flamenco Beach is not the place to be when a swell is running!

Back around the west side of Culebra. We wanted to check wind and swell conditions in the unlikely event it was comfortable enough of a ride to attempt the crossing to St. Croix. Nope! Despite southwest winds, the seas were still very much confused with the addition of a northerly swell.

OK, now where to? The wind direction was perfect to sail all the way around the northern side of St. Thomas to beautiful Magens Bay. With 25+ knots of apparent wind, we tucked in a reef in the main and the jib.

Sailing from Culebra to St Thomas with reefed sails

This was probably one of the most fun sailing days I’ve had on a yacht charter trip. The catamaran was easily cruising along at 8 knots and clocked 10+ later in the day with following seas as we surfed the swell.

Our helmsman did have to take over hand steering as the autopilot wasn’t able to keep up with these rollers.

Cero Mackerel caught in the US Virgin Islands

We put 4 rods out and 2 handlines. Clearing sargassum was frustrating, and I think that definitely affected our fish count this trip. However, we had some good luck when trolling over the Grampus Banks. We hooked up on a cero mackerel and landed it. Finally, a fish worth eating! Cero mackerel is considered one of the top sushi eating fishes out there.

Magen's Bay USVI bareboat charter anchorage

At Magens Bay, we dropped anchor in about 30 feet. The yacht spun around quite a bit in this anchorage with strong winds still blowing out of the south and some backwinding in effect.

The anchorage was shared with a couple other boats, but we had plenty of elbow room. Some charter crews have complained about loud music and jet skis here, but we didn’t experience any of that.

The bay is truly stunning, and I’d recommend this anchorage to anyone planning a USVI bareboat charter.

To take the edge off a long day on the water, we took the dinghy ashore and cooled off with a bushwacker at the beach bar ashore. Back on the boat, we whipped up some cero mackerel sashimi for an appetizer, and sauteed mackerel with cilantro lime rice for dinner. Delicious!

Beautiful fall day at the Maho Bay mooring field on our US Virgin Islands bareboat charter trip
The gorgeous mooring field at Maho Bay

Day 5: Off to the beautiful beaches of St. John and the Virgin Islands National Park

OK, where to next? St. John was the logical next destination. We hadn’t planned to spend much time sailing the Virgin Islands here on this bareboat charter trip, but our inability to get down to St. Croix changed that.

Before setting off, we grabbed a taxi and made a quick run for a less expensive provisioning run at Cost.U.Less. Things would certainly have been more expensive at Cruz Bay, St. John. It took about an hour round trip, and was well worth the effort.

With lighter winds, we settled for motoring and cruised around the Hans Lollik islands just to the north. They are beautiful, and uninhabited, but we decided not to stop (there are 2 anchorages in settled conditions).

St John sunset on our USVI bareboat charter trip
Another great Virgin Islands sunset | Too bad I couldn't put up the drone in the National Park!

We slowly motored along the north shore of St. John close to the British Virgin Islands and took in the gorgeous surroundings. The Virgin Islands National Park is truly stunning. Maho Bay called to us with it’s busy beach and crews floating off the back of their charter boats. After being isolated for so long during the storm, we were ready for some people watching!

A cooler was packed, and ashore we went in the dinghy to chill out and have a beach day. We settled for liming away for a few hours and enjoyed the evening sunset show back on the catamaran.

North shore of St. Johnm
North shore of St. John looking west

Day 6: More beaching and a night out in Cruz Bay

After a lazy morning, we decided to stay put after having so much fun on the beach the previous day. Maho Crossroads is a good option for to go beach bar fare to eat on the sand.

Sometime mid morning, a sailboat caught fire to our west. The crew got out safely from the traffic we heard on the radio.

Sailboat fire north of St. John USVI
Sailboat fire we saw to our west

Later in the afternoon, we were ready for a change of scenery, and perhaps a night where we didn’t have to cook. With that in mind, we motored back west to moorings at Caneel Bay. Cruz Bay was redlined by our charter company and this was the closest overnight anchorage.

80s Night in Cruz Bay USVI
Some of our crew ready for 80s night in Cruz Bay

We donned our best 80s gear and dinghied into town for a couple drinks and dinner.

Cruz Bay was so much fun! The people were friendly and it has a great local vibe. We started and ended the evening at The Beach Bar (yes that’s it’s name) where we had beached our dinghy. Did you say live music and dancing??

Christmas Cove anchorage on our USVI bareboat charter in the US Virgin Islands
The anchorage at Christmas Cove near St. Thomas

Day 7: Last day of the USVI bareboat charter: more fishing and back to St. Thomas

We rubbed our bleary eyes and cruised back around the north shore of St. John before heading down to the South Drop for some trolling. Again not much on the fishing count to report! In fact, I don’t think we had any bites on the over the drop itself, just on the shelf.

Oh well, it was still fun getting the sails up for a couple hours on the water.

As a last night’s anchorage, we chose the Christmas Cove mooring field. On our last morning, it would only be an hour motor back to Frenchtown Marina. I had thought Pizza Pi VI would be back in action for the season, but I think we were a few days too early.

Christmas Cove was fine, but it was probably my least favorite anchorage of the trip. Besides the convenience, there just really wasn’t much to do there. There are no beaches, the mooring balls are close together, and the snorkeling wasn’t that interesting.

We did have some catch and release fun with a school of jacks that hung around the boat and our blue underwater lights.

Had I another shot with my USVI sailing itinerary, I probably would try Water Island next time.

The sunset over Red Hook, St. Thomas, however, was pretty epic.

Check-out day: A smooth return of the catamaran

Not much to report for our last day, which is what you want! After a short motor back to the Charlotte Amalie area, we stopped at Crown Bay Marina to refuel. We raised them on Channel 16 and were able to come right in. The fuel dock is immediately to starboard after entering.

Back at Frenchtown Marina, we grabbed one of the Waypoints moorings and notified them by cell phone. The Waypoints team quickly came out to conduct the sail check before handling the med mooring back on the dock.

The check-out briefing also went smoothly and only took about 20 minutes.

I can’t wait to visit the USVIs on a bareboat yacht charter again! On our next BVI charter, I would even think about hopping over to St. John for a couple days. While the British Virgin Islands get most of the attention, crews should give USVI a closer look!

Thanks for reading my post about our USVI bareboat charter trip! If you enjoyed it, please subscribe or check out some of my other articles, like this bareboat charter beginner’s guide.

Final Preparations for a Yacht Charter Trip

Boat Trip Planning - watching the weather models

We are just weeks away from my next bareboat yacht charter trip – this one is a bit different. The plan is to sail the US Virgin Islands and Spanish Virgin Islands, including a couple deepwater crossings to and from St Croix (weather permitting!). We are also going to do a lot of fishing from the catamaran.

You can read more about my plan in this post, Sailing to St. Croix.

I’ll post some regular updates at the Yacht Warriors instagram account if you’re interested in following along.

To ensure a smooth, and (hopefully) stress free trip, we are always busy with final plans and preparations in the days leading up to a trip. I thought I’d share some of what I’m working on.

Boat Trip Planning - watching the weather models
A possible disturbance popping up that could affect our sailing itinerary | Source: Tropical Tidbits

Watching the weather like a hawk

The trend is your friend. This is especially true when chartering during hurricane season. While November is well past peak season, disturbances can still spin up.

In recent days, I’ve consistently seen several storms showing up on longer range weather models. One has turned into Potential Tropical Cyclone 15 which will move on to the west and be a non-issue for us.

There is, however, another weak disturbance that could bring 30 knots of wind during the middle of our trip.

It’s too early to tell exactly what impacts it could have, but I like to watch the trends and see how the forecast evolves. If confidence builds for that scenario, we’ll want to make sure our itinerary includes an anchorage where we can hunker down for 24 hours or so.

As we get closer to our departure day, I’ll start watching NOAA’s 5-day marine forecast. This should give you a good idea as to conditions you are likely to experience.

Weather routing on a crossing to St Croix
Example of what an unfavorable forecast could be crossing to St. Croix, with moderate SSE winds | PredictWind

For the crossings to and from St. Croix, we may need to adjust our itinerary for days with more favorable conditions. Or, we may have to cancel those plans all together. Under what conditions would I want to change those plans?

  • 20+ knot winds – this could make for a rough ride

  • Light wind, less than 10 knots – we don’t want to motor

  • Unfavorable wind direction – while the trades tend to blow out of the NE in the fall/winter, they can be bent further into the SE or S with passing disturbances

At the base on a previous charter trip getting ready to board, this one at Scrub Island in the BVIs

Final communications with the charter base

I always like to try and connect directly with the charter base if possible, in the days leading up to our departure. You’ll need to try and find the right contact – it’s usually not the charter specialist that helped book your trip.

There are two objectives:

  1. To try and position ourselves first in line for the charter briefing the morning after our sleepaboard. This can be the difference between leaving the dock at 9:00, or departing two hours later at 11:00. This doesn’t always work, but you miss every shot you don’t take.

  2. To confirm boat equipment, such as portable a VHF radio, rod holders, gaff, type of grill, etc.

For the first time, we are experimenting bringing our own frozen meats with us

Getting the crew involved

As the skipper, don’t try and do everything yourself! Most people love to help out and enjoy getting involved. Here are some activities I’ve delegated for this trip.


This is a great one to delegate to one or two crew members that have some logistics savvy.

By this time, we usually have finalized our menu plan and detailed list. The final step is coordinating for delivery of the food, beverages, and booze.

Or, there may be certain items that may need to be picked up in person. Each sailing destination is different.

For the US Virgin Islands, our crew decided delivery of everything with one company to be the best option since we have late arriving flights. If we had arrived earlier, you can really save quite a bit by shopping in person. We are paying extra for the convenience factor.

The USVIs also have several options where you can order online and just show up for curbside pick up – a good compromise.

We are also trying our hand at bringing frozen meats with us for the first time. We picked up some filets from Costco and pre-cooked some other meals like taco meat and chicken. TBD if it is going to be worth the extra effort ahead of time!

fresh mahi caught on a sailboat
Mahi we hooked previously on a trip in the Virgin Islands

Fishing licenses & regulations

There’s a lot to navigate when it comes to fishing in the USVI and Spanish Virgin Islands. There are federal waters (>3nm offshore), territorial waters, and the Virgin Islands National Park. Each has its unique license requirements, seasonal closures, and bag limits.

Additionally, there are numerous marine parks and protected areas that we’ll be passing through, such as the Coral Reef National Monument, East End Marine Park, and Hind Bank.

While at this point we are all familiar with the various rules, we have one crew member that is our designated expert to help make sure we fish lawfully throughout the trip.

Clearing customs into Culebra

We are required to clear customs when entering Culebra (Puerto Rico) from the USVI. Since we are all US citizens, this can be accomplished remotely with the CBP ROAM App.

One crew member has taken the lead in getting the app setup with the correct vessel and passport/known traveler numbers.

While I’m focused on navigating through the Ensenada Honda channel and getting us anchored, they can begin the check in process with CBP.

Sailing to St Croix: East End on St Croix USVI
View of the east end of St Croix with Buck Island in the distance

Buck Island Permit

We are going to sailing south to St. Croix, and one of the attractions is the Buck Island Reef National Monument. To visit though, you need anchoring permit.

I had a crew member help by obtaining the vessel registration and submitting the permit to the National Park Service for approval.

Sailboat Fishing Guide: How to Fish from a Sailboat

Mutton snapper caught while trolling in the Virgin Islands

Sailboat fishing is one of my favorite activities during our boat trips. Fortunately, many of the most popular sailing destinations like the Bahamas and British Virgin Islands (check out my BVI specific fishing tips or Exuma fishing guide) are also excellent places to fish.

Even if you aren’t an experienced angler, with a little planning you can have a lot of success. Here’s what you need to know to catch some serious fish and turn your yacht into a fishing sailboat.

Table of contents:

Fishing tackle and equipment

Northern Exumas Wahoo
Wahoo we caught with a diving lure in the Exumas

To rent, or to bring your own?

On our first few trips, we rented fishing equipment, but now we bring our own quality gear. A few things to consider…


Most charter companies should have an option to rent a rod, reel, and small tackle box for around $20/day. They will also provide a rod holder and gaff. Check in advance if they offer this option and what is included. You should expect to bring your own lures and additional fishing tackle.

Ye be warned: don’t expect quality gear – we’ve had a lot of problems the few times that we’ve rented. The equipment gets a lot of use and tends to be poorly maintained.

Renting is the cheaper option if you aren’t serious about fishing. Buying your own equipment is an investment that will take a couple trips to payback.

For smaller reef fish, the rented equipment should be just fine! If you want to go after the bigger pelagic deepwater fish, consider bringing your own setup.

Bring your own gear

The biggest factor to consider with bringing your gear on these fishing trips is the added headache of dealing with the airlines. You’ll need to check your rods and potentially pay an extra fee. United, for example sometimes tries to charge $200 if the container is over a certain length. If you have preferred status with an airline, you might be immune.

You should also plan to check fishing tackle and filet knives.


I have two, 6 foot jigging rods that I bring. If you have a local fishing store (mine is Fishing Tackle Unlimited), ask them what they’d recommend – there are lots of options. You can get away with shorter rods for trolling – it might help save you money on airline fees.

I like the jigging rod since you can use it for lower speed trolling, jigging, and bottom fishing. If you bring spinning reels, you can also use them for casting.

I use this Plano rod tube to transport my rods for every trip – it’s affordable, fits several rods, and is adjustable depending on the length you need.

Plano Rod Tube (TackleDirect)

This is the Plano rod tube I use to transport my two rods. It's made it through 7 airline flights now.


I use Shimano TLD 30IIAs. This was a recommendation from a friend that does some serious marlin fishing in the Gulf of Mexico.

Here’s why the 2-speed reel is great for sailboat fishing. When sailboat fishing under sail and you land a good size fish, you can’t just stop and you can only slow down so much with course corrections. The 2-speed reel lets you use the low gear to deliver more power to the fight.

Check out the picture below of the cero mackerel we caught on a 2022 trip to the USVI and Spanish Virgin Islands. We were sailing in 30 knots of apparent wind and had a reef in the main and jib. At the time we hooked up we were sailing at 9-10 knots and were only able to slow down to about 7.5 knots while we reeled it in.

I have the reels spun with 65 pound braided line (braid) and topped with 80 pound mono line. 

Yes – this is probably overkill but I would rather be ready when hook up that monster wahoo.

Spinning reels are also great – if you come up on a school of mahi-mahi, stop or slow the yacht, and cast some lures out. Keep in mind if you plan to use them for trolling, you won’t be able to have as much line on them as compared to trolling (or conventional) reels.

Shimano TLD-30IIA reel (TackleDirect)

This reel might be oversized for some of the fish you'll catch, but the 2-speed reel will help when you aren't able to take the sails down and have to keep moving.

Cero Mackerel caught in the US Virgin Islands
Hauled in a Cero Mackerel in the US Virgin Islands, one of the top fish species for sushi
Fishing tackle for bareboat charter trip
Prepping some lures and tackle ahead of a bareboat sailing trip

Other equipment for fishing off a sailboat

For my tools and knives, I use BUBBA products. You’ll get their famous non-stick grip and high-quality materials that will within stand the saltwater. These things will last for years.

Filet knife – I highly recommend bringing your own, well-sharpened filet knife. The boat is unlikely to have a knife sharp enough for the job. You also want a blade that is flexible. We brought this KastKing knife on our recent Exumas sailing trip and it worked great!

BUBBA 7 Inch Tapered Fillet Knife (Amazon)

Razor sharp and comes with the BUBBA non-stick grip.

Exuma fishing tips: filleting a wahoo in the Exumas
Filleting a freshly caught wahoo in the Exumas

Pliers – I use them to help remove hooks and to cut wire leader.

BUBBA Stainless Steel Pliers (Amazon)

These pliers won't rust and they also come with crimper and cutting features.

Casting net – I do not bring one of these, but you can if you are a serious angler and have an idea where to catch them. Some countries may not allow them, so make sure you double check the rules.

Trolling hooks – bring some #7 or #8s, such as Mustad Big Game Stainless Steel. The stainless steel are more expensive, but are resistant to saltwater. You’ll use these hooks to set up your skirted lures and ballyhoo rigs (if you can find frozen ballyhoo).

Mustad Big Game Stainless Steel Hooks (TackleDirect)

These are the sharpest hooks you can find and the stainless steel will help prevent rusting in between trips.

Bait circle hooks – I like Gamakatsu #7s. The circle hooks are best for bottom dropping with live/dead bait. The fish is most likely to swallow the bait whole, and the circle hook helps to prevent the hook from getting stuck in deep. Rather, they are designed to hook them in the mouth.

Gomakatsu Circle Hooks (TackleDirect)

These are great hooks to attach some live/dead bait and set on the bottom. Use the Double Dropper Rig (video below).

Live bait net – I’m usually able to catch a couple live bait on sabiki rigs each trip. I keep them alive in this Lindy Bait Tamer. 

Catching live bait blue runners with a sabiki rig
Catching some blue runners for live bait slow trolling | We keep them alive in a bait tank
Lindy BaitTamer (Amazon)

This one is right-sized for a bareboat charter and has held up over several trips. You can keep it in the water when you are at anchor. When moving, put it in a bucket and change the water every hour to keep the fish alive.

Gloves – I would consider this optional. We usually have a pair on hand to search for spiny lobster. The gloves can make it easier to handle a fish without the help of a gaff or net.

Weights – you’ll want a couple for bottom dropping. The deeper you drop, plan to go heavier.

Swivels – you’ll attach these to your primary line to quickly swap out pre-rigged lures. Look for ~75+ pound rated ball bearing swivels with snap connections.

Wire leader – we attach 2 feet or so of steel leader often when trolling since we catch a lot of toothy fish (barracuda, mackerel, and wahoo). This will help you catch more fish and lose fewer lures. Check out Malin Hard-Wire stainless steel leader. No. 6 (61 pound) will do. Check out this youtube video that shows you how to rig up a wire leader with the haywire twist.

Malin Stainless Steel Leader (TackleDirect)

Attach a copy feet of this leader to your rigs to prevent line breakage from tooth fish (like wahoo).

Fishing techniques and the lures to bring

Trolling lines are in the water - this is what our setup looks like

What is the best way to go fishing from a sailboat? These are your best options.

Trolling from a sailboat for bluewater sportfish

Most of our fishing is done when we are underway. It’s fun to always to toss a line knowing something could hit your lure at any time.

This is also the best way to cover a lot of distance, do some offshore fishing, and hook up on some game fish. We also do it in 30 feet of water too!

Check with your charter company ahead of time and make sure they include rod holders on both the port and starboard side of your charter boat. It’s also a good idea to bring carabiners to tie the reels to the boat. We’ve had a rod holder break on us before and it saved us from losing the whole setup.

You can also bring your own rod holders to clamp on to the railings – not all sailing yachts come with them and the charter company may not have spares.

Amarine Rod Holders (Amazon)

These are an affordable option for clamp on rod holders in case you want to bring your own.

King mackerel caught in Key West
King mackerel caught while trolling with a ballyhoo rig and Ilander lure skirt

We will usually pull one line at the top of the water (or slightly below) and a second 10-20 ft deep using a diving lure.

At the top, we use Iland Ilander Trolling Lures with weighted heads to keep the lure just below the surface. We use the 8 1/4 inch length and I like blue/white, pink, and black/purple. Get a variety! If we have dead bait such as ballyhoo or mahi belly, we will rig the skirt with them.

Iland Ilander lure (TackleDirect)

This is a great all-around surface lure that you can often catch mahi, tuna, and king mackerel with. Blue/white, pink, and black/purple are my favorites.

Iland Ilander Flasher Series lure (TackleDirect)

Try a couple of the flasher skirts as well - the reflective mylar helps to attract some fish species.

Fathom Offshore Calico Jack Slant (TackleDirect)

This Fathom lure has a tapered nose that creates great swimming action. It also comes pre-rigged on 12' of mono and includes a stainless steal hookset.

Check out this video on how to rig a ballyhoo for a skirted lure.

For the second rod, we’ll use an artificial diving lure. I like the Rapala X-Rap Magnum and the Yozuri Bonita (look for them in 5-6 inch sizes). They have great action and will dive 10-20 feet below. These are your best bet for catching wahoo.

Yozuri Bonita lure (Tackle Direct)

This has been my most successful diving lure recently, and I caught my first wahoo with it. In 6 3/4 in size, try the Flying Fish, Red Black, and Purple Black.

Rapala X-Rap Magnum lure (Tackle Direct)

Try these in a variety of depths from 15-40 feet. I like Hot Pink, Bonito, and the Green Mackerel colors.

Shark bait in the Exumas
Yo-Zuri Bonita lure (Flying Fish) on a fish that we didn't reel up fast enough!

Experiment with distances – we like to mix it up, and there is no perfect formula. We usually put one line ~75 feet out and the second ~125-150 feet behind the sailboat. You can mark the line with a sharpie to help you quickly get lures back in the water after checking them.

If you notice lots of sargassum seaweed in the water, check those lures frequently and clear them if necessary. While this can be frustrating, the good news is that mahi mahi like to hang out under seaweed lines.

Catching sargassum
This is going to happen to you! Check those lines often.

Casting for mahi-mahi or tuna on the surface

This technique has worked for us a couple times. I also see it successfully done all the time on deep sea fishing charter videos such as StanzFam.

The idea is that while trolling in deeper water, you might come across a school of mahi or tuna. What do you look for?

  1. Birds or a disturbed water surface. This usually means the birds and fish are attacking a bait ball. Go join in on the action! They are in a frenzy and will eat anything.
  2. Mahi-mahi love to hang around weed lines or other floating debris. It is said they don’t like the sun very much. Get close to investigate – you can often see them in clear water.

Stop the boat, toss in some lures, and quickly retrieve them with the reel. This is best done with a spinning reel, but it can work with conventional reels as well. Bring a couple popper lures such as the Rapala Magnum Explode. Tady Lures are another great option.

If you have live bait, even better!

Here’s a variation of this technique: you just caught a mahi. If you can stop the sailboat, see if it’s friends come to investigate. They usually do!

Mahi hook up in the Virgin Islands
Schoolie mahi-mahi caught on a recent trip along a weed line using an Ilander lure

Bottom dropping for reef fish species

Occasionally we’ll stop over a reef and drop a couple lines down to target snapper and grouper. You can even use this technique when at anchor.

We use two hooks on a dropper loop knot and put on some live or dead bait (even if it’s a piece of raw chicken). This video is a great overview of how to tie the knot.

Drop it down and wait for that monster grouper to hit your line!

This technique is hit or miss when sailing. Most fishing boats or fishing charters that use this technique have a sonar fish finder to help them target the fish. Doing it on a sailboat is somewhat of a guessing game, but it has worked for us before. Try and find something with good bottom structure if possible.

Jigging for bottom fish

This technique also targets bottom fish. Drop your jigging lure and let it sink close to the bottom. Once it’s down, pull up quickly once or twice and then let it sink back down. You can also try this in different directions.

For lures, the Tady Lures mentioned earlier are a great option. I also like Berkeley Fusion Bucktail Jigs – try the 3 ounce version in pink colors.

Little tunny caught trolling near Key West
Little tunny we caught trolling in ~40 feet of water

Where to fish while sailboat fishing

The obvious answer for me is: anytime we are sailing or moving the boat!

If you are trolling in less than 60 feet of water, you are likely to only catch mackerel, barracuda, and potentially some reef fish like mutton snapper.

To turn your sailboat into a sportfishing boat, let’s head for deeper water. I like to use the Navionics Boating App to help plan our routes. The Sonar Chart and Relief Shading layers help you pinpoint bottom structure and shelfs where the water quickly drops off.

You can have a lot of success trolling over bottom structure – anywhere that might provide a habitat to fish. Where there are small fish there are sure to be bigger fish. Also look for non-dangerous wrecks on your charts.

Drops are where the water can quickly fall of from 100 feet to thousands in a short distance. Troll back and forth over this if it will fit in your itinerary. The BVIs, Spanish Virgin Islands, and Exumas all have drops that you can fish during your charter trip.

The picture below is from our sailing trip to the Spanish Virgin Islands where we had a great fishing experience. We caught mahi-mahi, mutton snapper, yellowtail snapper, king mackerel, barracuda, and more. We also did pretty well on a recent bareboat trip to Key West.

Each pin represents a fish caught during that morning we sailed around the eastern end of Vieques. We weren’t able to reach the drop farther south (black and purple shading) due to sailing conditions (the trades were really blowing), but we trolled over the first shelf drop and other bottom structure.

Fishing route in Vieques
Trolling route around the shelf area at Vieques in Puerto Rico | Pins represent fish we caught (source: Navionics)

We've caught one, now what?

Well first, get it on the boat!! Our setups described above are usually strong enough to pull the fish straight up onto the steps on the back of the pontoons of our catamaran. We don’t usually worry about the line snapping

If you are sure you’ve landed a keeper, you can also grab it with a gaff to make sure you don’t lose it at the boat. I have not seen many of these on charter boats, but you can ask for one if you rent gear.

For hook removal, we simply use a pair of pliers and gloves. The goal is to get that fish back in the water as soon as possible if it’s catch and release.

How to fillet your fish

I think the absolute best resource to learn is by watching videos. Captain Nick Stanczyk is the expert I turn to. Check out his youtube channel StanzFam. He usually filets fish at the end of every episode, and the videos are really fun to watch.

Filleting a mahi mahi caught in the Virgin Islands
Fileting a mahi at the swim ladder

These are the fish that we would keep if caught:

  • Mahi-mahi
  • Tuna (yellow, blackfin, bonito)
  • Wahoo
  • Snapper
  • Grouper

There can be some varieties of these, so just be sure you are keeping the good eating ones. For example, a little tunny looks similar to bonito, but are not good eating at all. Check out my guide to the different types of fish in the Virgin Islands. Most of these fish can be caught all throughout the Caribbean.

If you are fishing in areas with ciguatera poisoning, double check local guidance before eating any reef fish.

We always bring supplies to make fish tacos and ceviche (yellow tail snapper is great for this). Simply grilling up some filets with olive oil, garlic, and lemon is also hard to beat.

Fresh caught ono poke bowl
Fresh ono (wahoo) poke bowl from our recent Exumas trip

If you’ve enjoyed this post and are new to bareboat charters or sailing vacations, check out our starter guide here.

Thanks for reading my post about sailboat fishing! If you enjoyed it, please subscribe or check out some of my other articles, like this one about the fish of the Virgin Islands.

Fish of the Virgin Islands

Fish of the Virgin Islands

The fish of the Virgin Islands are similiar to what you can expect elsewhere across the Caribbean, from the Bahamas to Grenada.

Many of them, are delicious eaters, and others, fierce fighters.

If you’re planning a yacht charter or are thinking about booking a fishing trip, these are the fish you are most likely to encounter in the Virgin Islands. That includes the British Virgin Islands, Spanish Virgin Islands, and US Virgin Islands.

If you want to learn more about fishing techniques in the Virgin Islands, check out my tackle and fishing technique recommendations here.

Offshore fish of the Virgin Islands

Location: north and south drops, or in the deep water between St. Thomas/St. John and St. Croix.

Offshore is my favorite place to fish in the Virgin Islands. We typically head out to the north or south drop and troll back and forth in 200 to 600 feet of water.

Since we are usually sailing, we’ll have two lines out – one surface lure such as an Iland Ilander skirt. The second is a diving lure such as the Yozuri Bonita.

Here are the offshore fish species you can expect to catch:


Exuma fishing tips: filleting a wahoo in the Exumas
Here I'm fileting a fresh caught Wahoo to prepare it for sashimi and poke bowls on the catamaran
Fresh caught ono poke bowl
Wahoo poke bowl

Wahoo is by far my favorite eating fish that we catch. It’s great as sashimi and in poke bowls, or grilled up in fish tacos.

The wahoo fishing is always better in the fall, beginning in November, although it’s possible to hook one anytime of the year.

Since they claim to be the fastest fish in the ocean, they are also a lot of fun to fight. On my last trip, a huge one ran out most of my line and then snapped the 80 pound braid!

We’ve always had more success with wahoo using diving lures that swim 15+ feet below the surface of the water, such as the Yozuri or Rapala X-Rap Magnum.

Mahi Mahi (dolphin fish)

Filleting a mahi mahi caught in the Virgin Islands
Shot of me filleting a schoolie mahi mahi caught on a shelf area near the South Drop

Mahi are unmistakable with their shades of green, yellow, and blue.

You can catch mahi year round, in the shelf areas, as well as offshore.

Look for floating debris or sargassum – they don’t like the sun and enjoy shading themselves beneath. If you can see them, stop the boat and cast a popper lure near them. They can’t resist.

Mahi always become great candidates for fish tacos on our yacht charter trips. They are also excellent sauteed and crafted into a sandwich.


Yellowfin tuna

Yellowfin tuna are also easy to identify with the yellow markings and distinctive sickles. They can get quite large, compared to their cousins the blackfin and skipjack. Skipjack can be distinguished from blackfin with their horizontal stripes on the belly.

Tuna can be targeted by trolling using skirts and diving lures. If you see birds attacking a bait ball, that’s also a good sign tuna can be near.

Yellowfin is the best eating tuna, but all three are worth eating. Straight up with some soy sauce or cooked rare is the way to do it.



Blue marlin hooked up

Honestly, I’m not ever intentionally targeting marlin. If we ever caught one it would surely be released. I really don’t want to have a several hour battle either since we usually have a lot of ground to cover on our sailing trips (such as my crossing from St. Croix to Culebra on my Fall 2022 trip).

They can be caught in the Virgin Islands though, and it’s great fun if you have the right equipment and sportfishing boat.

Try pulling some bird teasers behind the boat to help raise them to your lures.

The size of the marlin that can be caught on the north drop is something of legends. You can also encounter marlin in the deepwater between St. Thomas/St. John and St. Croix.


Sailfish are typically caught for catch and release beginning in the fall months when the water begins to cool.

If you know where to look, you can see them surfing swells at the surface when their distinctive sail breaks the water. Anglers can then target sailfish by casting a surface lure or live bait to them.

Inshore Virgin Islands fish species

Location: shelf and reef areas, <150 feet

Inshore areas are great for bottom dropping, drift fishing, or fishing off the back of the boat while at anchor.

If shallow enough (I’m only a beginner at spearfishing), we’ll hop in and try and shoot with with a Hawaiian sling or speargun.


Catching barracuda in the Caribbean

This is, without a doubt, the fish we catch most frequently while trolling. They just can’t resist my lures, I guess!

They are fun to catch, but not the ones we want to eat. With the potential for ciguatera poisoning, especially the larger ones, we always release them. 

Another reason we don’t eat them? They smell…apparently the meat doesn’t but their skin is another story.


King mackerel caught in Key West
King mackerel we caught in about 50 feet of water

I’ve yet to catch a spanish mackerel, but for some reason we have hooked plenty of king mackerels. You can tell the difference since the spanish mackies have distinctive yellow spots.

Spanish mackerels are the better eating fish. King mackerels are oily and require a different type of preparation, such as by smoking.

Toothy fish, similiar to the wahoo and barracuda, you’ll want to use a wire leader if you think you might hook one.

Bonito (little tunny)

Little Tunny that I caught and released using a Iland Illander surface lure

Another fish on my list that we catch and release. I’ve just heard the meat is not that great to eat. They are shaped like tuna, but you can identify them by the squiggly dark lines on their back.


Jack caught in the Virgin Islands
Jack we caught with a surface lure while trolling over a reef in 50 feet of water

There are many different types of jacks. I think some are good eating, but I don’t have a sharp enough eye yet…we typically catch and release them if we hook one.

They can be caught while trolling and also while spear fishing.


Small grouper caught in the US Virgin Islands

Grouper is one of my favorite fish to eat.

Again, there several species, such as the black grouper and red grouper. You’ll want to make sure you are in compliance with fishing regulations. Sometimes there are certain seasons for these type of fish.

Also make sure you don’t keep any goliath groupers – they are typically off-limits all year round. Worth checking out the nassau grouper too, they are sometimes off-limits.

Groupers are best hooked while spearfishing or bottom dropping.


Snapper we caught in the Spanish Virgin Islands

Snapper is another great eating fish. The three most common you might encounter are yellowtail, mutton, and mangrove.

I’ve hooked both mutton and yellowtail before while trolling over a reef, but they are easier to target by spearfishing or bottom dropping.

Yellowtail snapper also like to congregate underneath your yacht. You can even chum the waters to attract them with leftover meal scraps. If you see this, put on some light fluorocarbon leader and some dead bait – you’re likely to get a bite quickly!


Tarpon under the yacht in the US Virgin Islands

You’ll often see tarpon in marinas near the areas where they throw fish scraps. In the British Virgin Islands, they like to hang out at Saba Rock, where they do a daily feeding.

These are definitely not eating fish – the meat doesn’t taste very good and the tarpon are quite bony.

You might, however, catch one if you drop a line down with dead bait in your anchorage. They are ferocious fighters and fun to catch!


Catching lionfish in the Exumas
Lionfish we speared on a reef in the Bahamas
Fresh caught lionfish ceviche
Lionfish ceviche appetizer on the boat - delicious!

Lionfish are in invasive species and can be taken any time of year. They don’t get very big, but the meat is excellent!

Spearfishing is the way to catch these suckers. For beginners, they make excellent targets since they aren’t afraid and don’t try to evade you (since they have no predators).

Check out my post about lionfish ceviche that we recently made in the Exumas. It has some cautionary notes about removing the venomous spines (painful but not life threatening).

Spiny Lobster

Fresh grilled Anegada spiny lobster
Fresh grilled Anegada spiny lobster on the boat | We got these from a local since tourists are not allowed to take them

Ok, not a fish, but worth mentioning.

Make sure you check local regulations, they differ, for example, between the USVI and BVIs. In the BVIs, tourists are not allowed to take them at all.

When in season and legal, we use a tickle stick and net to coax them out of their hideouts. A snare is also a good method.

Nothing beats fresh spiny grilled lobster with an epic Caribbean sunset (we’ve tried boiling too – grilling is better!).

Sailing in Puerto Rico: Spanish Virgin Islands Cruising Guide

Sunset at Green Beach Vieques

The Spanish Virgin Islands may be my new favorite caribbean bareboat charter destination. Solitude, beautiful beaches, and excellent fishing are just some of the highlights that rank highly on my list of must haves for a boat trip. Many people describe the SVIs as what the British Virgin Islands were 20+ years ago: raw, quiet, undiscovered – I was too young back then, but I’ll take their word for it!

Not too long ago, we visited Puerto Rico for this trip after a last-minute destination change due to Hurricane Eta in 2020 (we had been planning a Key West sailing charter). While it was stressful making the change within 72 hours of throwing off the dock lines, I am so thankful we decided not to cancel our trip altogether. This destination far exceeded my expectations.

Located just to the west of the USVI and BVI, the islands of Vieques, Culebra, and Culebrita dominate the Spanish Virgin Islands cruising grounds. You’ll find all sorts of habitats including mangroves, rocky coastlines, vibrant coral, and gorgeous caribbean sandy beaches.

Top highlights include hiking to the lighthouse on Culebrita, catching lots of fish, visiting the famous tanks on stunning Flamenco Beach (or Playa Flamenco) at Culebra, and witnessing the bioluminescence at Mosquito Bay.

There are several wildlife refuges which help protect and make the Spanish Virgin Islands such a special place. This includes the Vieques National Wildlife Refuge which used to be controlled by the U.S. Navy until 2003.  You can still find several anchorages marked as off-limits to anchoring due to potential unexploded ordnance.

Don’t expect beach bars at every anchorage. This is a place to get away from it all and soak in the natural surroundings. I’m really looking forward to sharing our experience with you and hope this cruising guide inspires you to visit this overlooked and beautiful cruising ground. Here is what I’ll cover:

SVI Logistics and Planning

Source: Puerto del Rey

Travel from the U.S. is easy with several direct flights to Puerto Rico from the mainland, and there is no passport requirement for U.S. passport holders. Sail Caribe operates out of Puerto del Rey –  the largest marina in the Caribbean.

Puerto del Rey is located in Fajardo, the boating hub on the Puerto Rican west coast. As you would expect, it has plenty of amenities which includes a small store for forgotten provisioning items. They also have golf carts that meet you upon arrival to take you and your gear down to your yacht.

You may also enter the SVI cruising grounds from the USVI, but make sure you are aware of the latest clearance requirements when entering and exiting. I talk more about how you can do this in my St. Croix and Culebra sailing itinerary.

Bareboat Charter Provisioning

Unloading at Puerto del Rey
Unloading upon arrival to Puerto del Rey

One thing that I love about this destination is that there is a Costco located in San Juan. We arranged with our charter company in advance for our driver to make this stop on our way to Marina del Rey.

This means cheaper prices and much more variety than what is typically available on a provisioning list. It is absolutely not as convenient (we arrived to the base after dark), but I think the payoff is worthwhile.  Worth noting that the Costco also carried beer, wine, and liquor.

OK, enough about Costco. Your charter will be able to provide you with a provisioning service so that you make your selections in advance and upon arrival, your groceries are already onboard. You may also have your driver stop at a grocery store along the way (such as Ralphs).

Additional Cruising Guide Resources

Given that the Spanish Virgin Islands are less visited than their sister islands to the east, there are not as many cruising guides available.  Stephen Pavlidis’ book Cruising Guide to Puerto Rico is your best bet. Be aware that the last revision was done in 2015, so some information could be out of date. It is still an excellent resource.

Cruising Guide to Puerto Rico (Amazon)

Stephen Pavlidis' guide has some great, detailed information on what to do and where to go. The last update was from 2015, so some information could be outdated, especially navigation info.

I also like to use the Navionics Boating App for planning. You can research routes, anchorages, and fishing spots. The ActiveCaptain Community feature is also very helpful to learn from other sailors experiences.

Here’s the link to the chart that was aboard our catamaran, although I don’t think it’s necessary to purchase ahead of time. There should also be a new edition of this coming out in 2022.

NV Atlas 11.1 Chart (Amazon)

Current edition of the SVI navigational chart that we found on our sailing yacht during our last trip.

When to go Sailing in Puerto Rico

An occasional squall is common, but they often don't last long

My favorite time of year to visit the Virgin Islands is April-May. The trades blow consistently out of the east at 10-20 knots. The weather is more settled and since this is considered the shoulder season, prices are cheaper.

Late November is also a great option, but the days are shorter and you run more of a risk of tropical mischief.

While the USVI and BVI can get very busy during peak season (Dec-Mar), I would not expect the SVIs to become quite as crowded. It sill flies under the radar as a destination and the bareboat fleet that serves the cruising grounds is much smaller.

For a more comprehensive overview of weather conditions, check out The Cruising Guide to the Virgin Islands. SVI is not covered, but the weather and cruising conditions information is applicable.

Cruising Guide to the Virgin Islands (Amazon)

This guide DOES NOT cover the Spanish Virgin Islands, but it has some info on weather and cruising conditions that would apply.

Northerly Ground Swells

Ground swells are common between November and April. Make sure you check the forecast since it could have an impact on your itinerary. Any anchorage exposed to the north, such as Playa Tortuga at Culebrita, will be untenable if a ground swell is running.

The NWS Marine Forecast will include information about ground swells. They are very well forecasted.

Spanish Virgin Islands Sailing Itinerary

Our suggested bareboat charter itinerary assumes 7 days on the water beginning in Puerto del Rey. We take you counterclockwise beginning south around Vieques Island and then north up to Culebra and Culebrita.

The prevailing trade winds in the Spanish Virgin Islands are typically from the east to northeast. Sailing counterclockwise will afford you some protection and more comfortable sailing conditions from the wind driven swell. Vieques and the other islands to the north will offer you some shielding as you sail east. When you make your turn back west, the swell will be at your back.

SVI sailing itinerary map
Map of our sailing SVI sailing route | Source: Navionics

Day 1: Overnight in Marina

We recommend coordinating with your charter company for an airport transfer from the airport to Puerto del Rey. They will be able to help schedule the pickup and make sure the vehicle is large enough for your crew and gear (and potentially provisioning items if you decide to stop on the way).

Get settled into your yacht, stow away your provisions, and familiarize yourself with the boat’s systems if you’d like. Crack a beer – you’ve arrived in paradise.

First night is spent overnight in the marina.

Day 2: Enjoy the Magic and Solitude of Green Beach

Green beach in Vieques
Enjoying the solitude at Green Beach Vieques

Distance on the water: 18 nautical miles

Time on the water: 3 hours

Try and set your yacht up to be first in line for the boat briefing and walk through. You don’t want to waste valuable cruising time in the marina! Ask for assistance with the lines. You may also ask the charter company to help with piloting the boat out of the slip.

Get that sailing playlist jamming and head southeast towards Isla Pineros – you may want to wait until you make the turn south before raising the sails depending on the wind direction. Get those fishing lines in the water – there is not a moment to lose!

If you have extra time you could head towards Cayo Santiago further down the coast of Puerto Rico. It’s known as monkey island. You can’t go ashore, but there is an anchorage on the west side. Drop the hook and dingy in closer to get a view of the monkeys which have been free roaming since 1938. There are approximately 1,000 rhesus macaques monkeys that call the island home.

Aside from the solitude, you come to Green Beach for the sunsets – they are epic with the main island of Puerto Rico and the El Yunque rain forest in the backdrop. Arrive early enough to also jump in the water for some snorkeling. You can expect to swim with sea turtles, rays, and lots of colorful fish. There are no amenities ashore, so plan to cook your first meal aboard.

Anchorage Details: the Green Beach anchorage is large and you’ll notice several markers on the chart. The water is usually crystal clear so pick a spot in 10-15 feet of water with a white sandy bottom. There will be areas of sea grass and coral/rock you should avoid. You are likely to have the place to yourself, but if you are there over the weekend, expect a few local boats that will join you.

Day 3: Explore the town of Esperanza and the Bioluminescence of Mosquito Bay

Mahi hook up in the Virgin Islands
Mahi hook up off the drop south of Vieques

Distance on the water: 8 nautical miles

Time on the water: 1.5 hours

Get underway and head southeast around the coast of Vieques. If you are into fishing from your sailboat, go far enough south to the drop – where the water depth changes from 100 feet to thousands. Troll back and forth across this area to target the pelagic species: mahi-mahi (dolphin fish), tuna, and wahoo.  This may be a bumpy ride given the strength of the tradewinds.

If you want to step up your fishing game, check out our sailboat fishing guide.

Tack your way towards Sun Bay Vieques. This a postcard worthy crescent moon shaped bay with a sandy beach and lined with coconut palms. It is just to the east of the town of Esperanza and within walking distance.

Anchorage Details: The best place to anchor is tucked up in the northeast corner to avoid as much swell as possible that wraps around into the bay. Holding is good in 10-20 feet with a grassy bottom. Make sure you get that anchor set. If the wind is really blowing, Puerto Ferro farther down the coast offers complete protection from all directions.

If you want to go ashore, you can beach your dingy on either side of the the swim buoys. Look out for the wild horses that may come up to say hi at the beach. Esperanza has a few options for dining and shopping. Use the cell phone service to check hours of operation since they may differ from what you’d expect.

Sun Bay can also be used as a base to tour Mosquito Bay, which has the claim to the brightest bioluminescence bay in the world. You’ll need to arrange a kayak tour as dinghies are not allowed. There are plenty of tour operators that can be found online and they will pick you up right at the Sun Bay Beach.

Day 4: Isla Chiva Lunch Stop and Beautiful Ensenada Honda

Anchoring at Isla Chiva in Vieques
Getting ready to dive on the anchor at Isla Chiva

Distance on the water: 10 nautical miles

Time on the water: 1 hour, 45 mins

This is another great day to check if the fish are biting as you continue your way east along the southern coast of Vieques. Before pulling into your anchorage at Ensenada Honda, make a lunch pit stop at Isla Chiva.

There are two anchorages, one on either side of the island. We recommend anchoring on the west side of Isla Chiva in 10-15 ft with a grassy bottom. There are a few patches of sand you can aim for when you drop the hook.

The beaches here are beautiful and you can often see the wild horses that come down to the shores edge. Dingy ashore for a picnic or enjoy the view from your catamaran (monohull is OK too!). 

Make sure you save some time for a snorkel over to Isla Chiva located at the dive spot marked on the charts. The last time we were here there were some large abandoned fish traps that were interesting to explore. If a SE swell is running or the trades are really blowing, snorkeling in this spot is not recommended.

Anchorage Details: Entering the Ensenada Honda anchorage can be tricky, but the charts are well marked – stick to the course shown on the charts. The water is not crystal clear so you’ll need to rely on your instruments and use extra caution. Depths range from 10-30 feet. We recommend tucking yourself farther in to the east side of the bay where it is shallower.

Ensenada Honda is extremely well protected. You will likely be the only boat here. Come here for the peace and quiet. There is no beach access given the mangroves that line the bay. For something different, launch the dingy and explore the mangrove river located in the far eastern edge. Expect to see some rays and a nurse shark or two if you are lucky.

Day 5: Head North to Culebra

Fishing route in Vieques
Great day fishing rounding the south coast of Vieques | Source: Navionics

Distance on the water: 20 nautical miles

Time on the water: 3-4 hours

Get an early start for a longer day on the water as you make the passage from Vieques to Culebra. Again, get those fishing lines in the water. We did really well hooking up in 50-100 feet of water (see pins in the picture above). Mahi and mackerel were the catches of the day.

As you round the SE coast of Vieques, you’ll see Culebra to the north, and if visibility is good, St. Thomas of the US Virgin Islands to the NW. 

The protected bay in Culebra is also known as Ensenada Honda (which means deep cove). This is your best opportunity to pull in for a provisioning stop in the town of Dewey and enjoy perhaps a beer or two at one of the local establishments ashore. Colmado Milka is well stocked with food, liquor and ice. Anchor close to the main town’s dinghy dock. Take your dingy there or motor under the Lifting Bridge where there are several other spots to tie off to.

Town of Dewey at Culebra
Dewey, the main town of Culebra

You can spend the night nearby, which could be a good option if you’d like to eat dinner ashore. Otherwise, make your way back towards the entrance to the bay and veer to starboard into the Ensenada Dakity anchorage. Taking a dingy ride from Ensenada Dakity to the Town Dock is another option if the weather is settled.

Ensenada Dakity is a lovely mooring field with great protection tucked in behind the reef. You’ll enjoy minimal roll and a nice breeze over the reef. The sunrises here are spectacular.

Anchorage Details: Grab one of the many (free) mooring balls that are available. You can also anchor in about 15 feet behind the mooring field. Be careful of your yacht’s draft – the mooring balls closest to the reef can be in <5 feet of water.

Day 6: Culebrita Day Trip and Carlos Rosarion Beach

View of Culebrita, one of the Culebra anchorages
Beautiful view of Playa Tortuga and the lighthouse at Culebrita

Distance on the water: 16 nautical miles

Time on the water: 2 hours, 45 mins

The islands of Culebra have a distinctly different feel than Vieques. Rather than one large island, there are many hidden gems to explore. The first must see place is Culebrita.

Get an early start and work your way north towards Cayo Norte. Giving the reef/rocks to starboard plenty of room, round the corner and pick up a mooring ball or anchor at Playa Tortuga (Turtle Beach). This was our favorite beach in all of the Spanish Virgin Islands. Crescent moon shaped, white sand, coconut palm lined, and few other visitors – what else could you ask for?

Make sure that there is no northerly ground swell forecast as this anchorage is exposed to the north. Your charter company is likely to require this as a day stop only for this reason.

Culebrita is a small, uninhabited cay with an abandoned lighthouse at its highest point. The only residents are wild goats that you will be sure to bump into. Grab a pair of hiking shoes you don’t mind getting dirty (mud, puddles, and goat droppings are expected), plenty of water, and head ashore.

Culebrita Hiking Map
Culebrita hiking map | Source: Google Earth

The hike to the lighthouse is about 3/4 of a mile and should take you about 20-30 minutes. You’ll be rewarded with a beautiful 360 degree panorama of the surrounding islands – the best view from any hike I’ve taken in the caribbean.

The old Spanish lighthouse dates back to 1886 and is interesting to explore. It is falling apart after battling it out with several hurricanes and it is not being maintained – use caution. You are not supposed to venture inside.

The north shore of Culebra may be off limits depending on your charter company, so retrace your steps and round the west coast of Culebra from the south. Grab one of several free mooring balls available at Carlos Rosarion. If swell is wrapping around from the north, try Tamarindo to the south which may offer better protection.

Relax, grab a sundowner, and enjoy the spectacular sunsets over the uninhabited cayos to the west.

Day 7: Hike to World Famous Playa Flamenco

Carlos Rosario sunset in Culebra
Great sunset over the uninhabited Cayos to the west of Carlos Rosarion

Distance on the water: n.a.

Time on the water: n.a.

Take a morning dip and enjoy some of the best snorkeling of the trip at Carlos Rosarion. It can be accessed right from your mooring and you may even see a scuba diving boat show up. There are several scuba operators out of Culebra that you can arrange a guided dive if you are interested.

We are staying put today, unless you’d prefer to explore Cayo Luis Pena. We’d suggest, however, going ashore for another hike to the world famous Flamenco Beach (Playa Flamenco). The trail is easily visible on satellite. Again, bring some shoes you don’t mind getting dirty. The hike is just under a mile and should take you about 30 minutes. The trail dead ends into the back beach parking lot.

Tank at Flamenco Beach
One of the tanks previously used as target practice at Playa Flamenco

While I haven’t been to the South Pacific, Flamenco Beach feels distinctly like a beach that could be located in Tahiti or the other Channel Islands. It also holds the title of one of the top 10 beaches in the world. Aside from the beautiful setting, the main attraction is the abandoned tanks scattered across the beach that the US Navy used for target practice up until the 1970s. 

Make a day of it and relax. Food, restrooms, and beach chair rentals are available.

Once back on your yacht, enjoy another great sunset. If the weather is settled and you aren’t worried about losing your mooring ball to another boat, I highly recommend an evening cruise. Make a loop around the Cayos to the west and enjoy the rugged natural beauty of the area.

Hiking back from Flamenco Beach
Hiking back from a visit to Flamenco Beach

Day 8: Return to the Marina or Overnight at Isla Palominos

Approaching Isla Palominos to anchor
On approach to pickup a mooring ball at Isla Palominos

Distance on the water: 20 nautical miles

Time on the water: 3-4 hours

Last day on the water! If you are fishing, head around on the north side of the Cayos de la Cordillera. This is another opportunity where the water gets deeper and you can catch some big fish. We hooked several mahi in this area the last time we visited. Let’s just say the mahi tacos for lunch were amazing.

Isla Palominos is a great last night anchorage. It’s close enough to motor home the next morning before you debark and head home. Or, you can put back into the Puerto del Rey marina if your crew would prefer showers and some shore power.

Isla Palominos is a very popular local destination, so don’t expect any peace and quiet! You have been warned.

Upon returning to the marina, your charter company may request that you first stop at the fuel dock – leave yourself plenty of time to checkout and return to the airport.

I hope you enjoyed my post about the Spanish Virgin Islands and sailing in Puerto Rico. If you are new to sailing trips and enjoyed this post, subscribe to my newsletter check out our beginner’s guide here.

Dream Yacht Charter Shutters two US Charter Bases

Stock Island Yacht Club and Marina sunset

Photo: the former Dream Yacht Charter base at Stock Island Yacht Club in Key West

Dream Yacht Charter, a global charter management company, recently closed two of their US bases in Key West and Puerto Rico.

Dream Yacht Charter Key West

The Dream Yacht Charter Key West base was opened up during Covid and was always planned to be temporary. With travel restrictions to other popular bareboat charter destinations, it allowed Americans to stay in the country and continue to take charter vacations.

With restrictions easing, the base was shut down in the summer of 2022.

This is not surprising, despite any success they may have had. The Florida Keys and the Dry Tortugas are a tricky place to charter. I visited the base in August 2021 for a visit to historic Garden Key. You can read about some of the challenges I experienced in my trip report

In addition, the yachts in the charter fleet can also likely earn more revenue in the more desirable destinations, such as across the Gulf Stream in the Bahamas.

Dream Yacht Charter Puerto Rico & Spanish Virgin Islands

It’s less clear why the Dream Yacht Charter Puerto Rico base at Puerto del Rey was shuttered.

I also recently chartered with DYC in November 2020 to Puerto Rico, which serves the Spanish Virgin Islands cruising grounds. I got to see first hand why the base might be closed. 

Two reasons why they might have done this:

  1. Not enough demand from charter customers. With lower revenues, yacht owners may have requested their sailboats be moved to busier locations, such as the next-door US and British Virgin Islands. The Spanish Virgin Islands are still relatively undiscovered. I do think in the long-term, popularity will grow. You can read more about them in my cruising guide.
  2. I think the base was understaffed, which led to lower customer satisfaction. In turn, charter customers chose other options due to reputation damage. It was clear to me the small fleet was had a significant amount of deferred maintenance and a team that wasn’t able to keep up.
Puerto del Rey on the eastern coast of Puerto Rico, just a couple hours from the Spanish Virgin Islands

Other charter company options in Key West and Puerto Rico

In Key West, the Moorings and Florida Yacht Charters partner to offer a small bareboat charter fleet in the Keys and Dry Tortugas.

Sail Caribe has a Puerto del Rey base for the Spanish Virgin Islands. You can also charter out of the USVIs and clear into customs to visit Puerto Rico. I wrote about how to do that for an upcoming yacht charter trip I have planned to the US and Spanish Virgin Islands.

The Best Caribbean Bareboat Charter Destinations

Best Caribbean Bareboat Charter Destinations

While far-off, exotic yacht charters might be intriguing, nothing beats a Caribbean bareboat charter destination right in our own backyard.

Tropical sandy beaches, steady trade winds, lazy beach bars, and convenient travel options characterize a visit to these many islands.

And if you’re limited to a week or 10 days, you’ll get to spend more time on your catamaran with a tropical beverage, and less stuffed into a crowded flight.

From Grenada to Puerto Rico, nearly every country in the leeward and windward islands has a Caribbean sailing vacation option for you.

If you are still early in your chartering journey, these are the top 5 Caribbean bareboat charter destinations you need to explore. They are the best sailing trips for beginners.

You can visit each many times, and still find new fresh adventure on a return trip.

I’m on my 9th yacht charter (still in my 30s), and I’ve only visited one destination outside of these top 5 (Key West and the Dry Tortugas).

Virgin Gorda Sound sunset with Saba Rock in the background (Pre-Irma)
Sunset at North Sound, Virgin Gorda in the BVIs

British Virgin Islands

Yes, the British Virgin Islands is the obvious choice, but you have to put it first on the list. It’s the global yacht charter capital.

Not only is the BVIs the best place for first-timers, but you’ll find yourself returning year after year. There’s something about it that keeps drawing you back.

I’ve spoken with some old salts that have made over 30 trips!

It’s popularity owes itself to the unique geography, with many islands and bays to explore, sheltered from the trade wind driven swells.

The sailing is predictable and navigation is easy with short, line of sight passages.

Beach bars, restaurants, and amenities galore, the majority of BVI’s economy caters to charterers.

My BVI FAQ page is a good place to start to learn more about the BVIs.

Boulders at Devils Bay at the Baths
Boulders at Devil's Bay | the Baths, BVI
Lagoon and beach at Cow Wreck
Lagoon swimming on the north shore of Anegada
White Bay JVD
Beach bars line White Bay, Jost van Dyke

Highlights of a British Virgin Islands yacht charter

  • Hike through the gigantic granite boulders at the Baths to Devils Bay

  • Anchor in North Sound and enjoy the sights of one of the finest harbors in the Caribbean

  • Sail offshore to the sunken island, Anegada. Sip cold beverages at rustic beach bars on the beautiful north shore

  • Go Beach Bar hopping for painkillers at famous White Bay, Jost van Dyke

  • Jump into the water from the second deck of the floating pirate ship bar, Willy-T

Sandy Cany sandbar in the Exumas
One of the many sandbars in the Exumas, this one at Sandy Cay

Exuma, Bahamas

Yes, I know, it’s not technically the Caribbean, but it’s close enough.

I love the Exumas for the fishing, solitude, and easy travel options from the USA.

This is also more of an advanced sailing destination and I would not recommend it until you have 2+ charters under your belt. You’ll need to anchor more frequently and pay close attention to weather, tides, currents, and depths. We first visited the Exumas on my third sailing trip.

The water in the Exumas is absolutely stunning, with some of the most vibrant turquoise blues I’ve ever seen.

If you want to learn more about the Exumas, check out my cruising guide.

Pirate's Lair anchorage at Warderick Wells
Pirate's Lair at Warderick Wells in the Exuma Land and Sea Park
Shroud cay anchorage and the mangrove river
Aerial view of the mangrove river at Shroud Cay
Wahoo caught on the drop in the Exumas sound
Catching wahoo on the drop in the Exumas

Highlights of an Exuma, Bahamas yacht charter

  • Visit the Exuma Land and Sea Park – our favorite mooring field is the Pirate’s Lair

  • Dinghy the mangrove river at Shroud Cay and hike up to Camp Driftwood

  • Pass through a cut to the Exuma Sound and fish the drop for mahi, tuna, and wahoo

  • Cross the Yellow Bank and stop for lunch at one of the many coral heads you’ll pass along the way

  • Grab a peanut colada at Staniel Cay Yacht Club and snorkel nearby Thunderball Grotto

Sunset at Green Beach Vieques
Sunset at Green Beach in Vieques

Spanish Virgin Islands

Part of Puerto Rico, they lie right next to the US Virgin Islands.

If you want to seek out the old school Caribbean vibe, the Spanish Virgin Islands are for you. They are far less popular and developed than their Virgin Island neighbors to the east.

The SVIs consist primarily of Culebra, Culebrita, and Vieques. There are also a number of smaller cayos to explore as well.

You can find two of the most stunning beaches in all of the Caribbean here: Playa Flamenco and Playa Tortugas.

If you want to learn more about the SVIs, I suggest Stephen Pavlidis’ Guide to Puerto Rico. You can also check out my cruising guide.

View of Culebrita, one of the Culebra anchorages
Tortuga Beach and the lighthouse at Culebrita
Tank at Flamenco Beach
One of the abandoned tanks at Playa Flamenco
Carlos Rosario sunset in Culebra
Epic sunset at a Carlos Rosario mooring ball

Highlights of a Spanish Virgin Islands yacht charter

  • Hike to the abandoned lighthouse at the top of Culebrita for incredible 360 views

  • Sip $2 Medallas from the vendors at Playa Flamenco

  • Snorkel the beautiful reef from your mooring ball at Carlos Rosario

  • Watch an epic sunset over the Puerto Rico mainland at Green Beach

  • Take a bioluminescence kayak tour at Mosquito Bay

Petit Rameau at Tobago Cays
The idyllic Tobago Cays, a must stop in the Grenadines

St. Vincent & the Grenadines

This is the only destination on my list I haven’t yet visited. We had plans, but were disrupted by Covid.

You’ll enjoy easy sailing, white sandy beaches, abundant marine life, and many vintage Caribbean beach bars to help cool you off.

You can do a roundtrip or a 1-way passage south to Grenada. This option avoids a potential uncomfortable upwind slog back to St. Vincent

Most people don’t spend much time on the main island of St. Vincent – the many unspoiled islands of the Grenadines to the south beckon.

If you want to learn more about the Grenadines, pick up a copy of the Sailor’s Guide to the Windward Islands.

Anchorage at Salt Whistle Bay
The anchorage at Salt Whistle Bay
Petit Tebac
Captain Jack Sparrow's island, Petit Tebac
The lone umbrella at Mopion Island
The lone umbrella at Mopion Island

Highlights of a St. Vincent and the Grenadines yacht charter

  • Visit the stunning Tobago Cays, snorkel the coral reefs, swim with turtles, and arrange for a lobster beach barbeque

  • Anchor at idyllic Salt Whistle Bay and walk along the beautiful palm-lined beach

  • Explore the island where Captain Jack Sparrow was marooned – Petit Tebac

  • Head to Mustique and grab a cocktail at the legendary Basil’s Bar

  • Get your picture taken with the umbrella on the castaway island, Mopion

Often photographed Trunk Bay at St. John, USVI

US Virgin Islands

During Covid, the US Virgin Islands made a resounding comeback due to travel restrictions elsewhere. Many long-time BVI visitors discovered the USVIs for the first time. Many were pleasantly surpised!

Why is the USVI appealing? Good provisioning options, cheaper prices, and direct flight options are a few reasons.

Consisting of St. Thomas, St. John, and St. Croix, most boaters spend the abundance of their time circumnavigating St. John and visiting the pristine National Park areas.

You can even use it as a jumping off point to explore the Spanish Virgin Islands.

Magens Bay USVI in St Thomas
The lovely bight - Magens Bay
Picturesque Dutch-inspired Christiansted in St. Croix
Beautiful Caribbean town of Christiansted, St. Croix
Ram Head and Salt Pond Bay

Highlights of a US Virgin Islands yacht charter

  • Lounge on the beach at Trunk Bay, the most photographed spot in the Caribbean

  • Be adventurous and conduct an offshore passage to St. Croix to visit the pastel-colored town of Christiansted

  • Stroll the lovely town of Coral Bay and grab a bite to eat or do some shopping

  • Sail the north shore of St. Thomas to the bight at Magens Bay. Simply enjoy the magical scenery or head ashore for a drink at the beach bar

  • Enjoy the solitude of the Salt Pond Bay anchorage – lime away the afternoon or hike for the views at Ram’s Head

Thanks for reading my post about the best Caribbean bareboat charter destinations! If you enjoyed it, please subscribe or check out some of my other articles, like this one about how the British Virgin Islands’ vibe is changing.

Top 5 Culebra Anchorages in the Spanish Virgin Islands

Ladies at Flamenco Beach

Often overlooked by it’s more popular sisters to the east, the USVIs and British Virgin Islands, the Spanish Virgin Islands continue to be a well-kept secret for those in the know. Don’t miss out on these spectacular Culebra anchorages!

I love them because they are less crowded, stunningly beautiful, and offer great opportunities for snorkeling and fishing.

In this post, I’ll cover my top 5 favorite Culebra anchorages to check out the next time you visit the Spanish Virgin Islands on a yacht charter. You can also learn more about them in my cruising guide. I’ll cover Vieques in another post.

DNR mooring balls at Culebra anchorages

Before we dive in, be aware that the Department of Natural Resources (DNR) has several mooring balls throughout Culebra. This helps protect the seabed and the National Wildlife Refuge areas.

Make sure you inspect these balls after tying off! Last time we visited we found at least one ball that didn’t pass for us.

Most are also marked as day-use, but this doesn’t seem to be enforced. Stay on them overnight at your own risk!

Last time we visited (Dec-2020), we counted the number of balls we saw. Here’s what we found.

Number of Mooring Balls
Bahia de Almadovar
Ensenada Dakity
Cayo de Luis Pena
Playa Tamarindo
Playa Carlos Rosario
6 (and 3 additional to the north marked for diving)
View of Culebrita, one of the Culebra anchorages
Beautiful Culebrita, one the of the Spanish Virgin Islands' gems

Culebra anchorages

Culebrita anchorage (Bahia de Tortuga)

Hands down, this is my favorite Culebra anchorage. Tortuga Beach is a perfect crescent shaped, palm tree-lined piece of paradise.

There are several (DNR) mooring balls here, which are designated for day use and are free. You can also anchor.

Many consider this a day stop only, since the anchorage is exposed to northerly ground swells. Passing tropical waves or strong tradewinds can also make Culebrita uncomfortable. Nearby Bahia de Almodovar is a good nearby, overnight alternative.

On weekends, it also might be crowded since it is often visited by the ”Puerto Rican navy”.

One of the many residents that calls the abandoned lighthouse home

What do to at Culebrita

I wrote a bit about Culebrita in my Spanish Virgin Islands cruising guide and include a map of the trails.

Get out your hiking shoes and make the trip to the lighthouse – expect them to get wet and quite dirty! The 360 views at the top of the surrounding reefs and islands is worth the effort.

You can also visit the jacuzzis on the north end of the island. These are natural tide pools that heat up with the warm tropical sun.

Other things to do? Just enjoy the beautiful beach. Swim with the sea turtles. Snorkel the nearby reefs.

Ensenada Dakity anchorage
Aerial shot of Ensenada Dakity | You can also see Puerto Rico in the background

Ensenada Dakity anchorage

Just inside the reef after entering Ensenada Honda, you can find this Culebra anchorage, Ensenada Dakity. There are 20+ mooring balls you can use.

Be careful of the front row! It can get quite shallow at low tide. Monohulls should avoid those.

Despite being exposed to the trades, you won’t feel much swell at all thanks to the protection of the reef.

I prefer to use this anchorage rather than anchoring closer to the town of Dewey. Go get your provisions in Dewey, but re-locate to Dakity for the night. It’s also within dinghy range if you prefer to go out for a bite to eat, such as at the popular Dinghy Dock.

What to do at Ensenada Dakity

Activity-wise, there isn’t much to do. It is a very pretty area though and serves as a great jumping off spot for excursions out of Dewey.

Snorkel the nearby reef right from your yacht and enjoy the golden hour with a cold one.

Cayo Luis Pena
Cayo de Luis Pena bird sanctuary as seen from the north

Cayo de Luis Pena anchorage

As you continue to work your way clockwise around Culebra, you’ll find Cayo de Luis Pena – the larger cayo on the west side.

You have several options for anchoring or mooring. I like Lana’s Cove on the southwest corner. It is better protected and offers you easy access to the hiking trail which runs to the north end of the island.

Cayo de Luis Pena is part of the protected marine sanctuary. Last time we visited, there were two DNR day-use mooring balls here.

The anchorages here are notorious for not being, well, comfortable. Surge and swell seems to wrap in at all of them. So, consider this a day stop only.

What to do at Cayo de Luis Pena

More snorkeling and exploring! The hike is fun – you’ll especially enjoy it if you are a bird watcher – the island is a sanctuary.

The beaches are mostly rocky, but they do the trick if you have a dog aboard.

Carlos Rosario sunset in Culebra
Epic sunset over the cayos to the west from our mooring

Playa Carlos Rosario anchorage

There are several (~6) mooring balls here. Otherwise it is too deep to anchor. The shelf drops off quickly from shore. The bottom is also not good for anchoring.

The moorings, as with the other DNR balls, are marked as day use only, but that does not seem to be enforced.

Hiking to Flamenco Beach from Carlos Rosario
Hiking to Flamenco Beach on the trail from Carlos Rosario

What to do at Cayo de Luis Pena

There is a super healthy reef here that is great for diving and snorkeling. Last time we were there on a catamaran we saw turtles, rays, and a few juvenile sharks. A school of yellowtail snapper hung around underneath our boat as well.

We also had to compete with some jellies, so take caution.

The hike over to world-famous Flamenco Beach is well worth the trip – the trail is quite easy to identify on Google Maps.

You will also experience amazing sunsets here. The cayos to west make for a perfect backdrop.

Tank at Flamenco Beach

Flamenco Beach anchorage

Use caution with this anchorage as it is very exposed to the north. This one only works in very settled conditions. I would definitely recommend this as day-use only.

You also might want to avoid if the wind direction has a northerly component.

If the wind is up, you might also have some difficulty landing the dinghy on the beach.

But you can’t miss Flamenco Beach. Other options are taking the hike from Carlos Rosarion or anchoring in Ensenada Honda and renting a street-legal golf cart.

Your author enjoying a beach day at Playa Flamenco

What to do at Flamenco Beach

The main attraction here is the wonderful beach. It reminds me of the South Pacific with it’s reef, coconut palms, and mountainous terrain.

Make sure to go get your picture taken with the tanks that were previously used as target practice.

Park yourself, grab a beer and some lunch, and enjoy. There are several vendors that sell food and drink.

Thanks for reading my post about Culebra anchorages and making it all the way to the end! If you enjoyed it, please subscribe or check out some of my other articles, like this one about sailing to St Croix and visiting the Spanish Virgin Islands.

Sailing to St. Croix: A Fresh USVI and SVI Sailing Itinerary

Sailing to St Croix: East End on St Croix USVI

Photo: Buck Island as seen from Point Udall – the easternmost point of the US

Thinking about visiting the BVIs again for your next bareboat charter sailing trip?

Think again.

Let’s ditch the tried and true and mix it up with a fresh, exciting sailing itinerary that few charter boats attempt.

My plan calls for a week in the US Virgin Islands and Spanish Virgin Islands. Specifically, we are going to go sailing to St. Croix from St. Thomas. Next we’ll continue clockwise to Culebra, SVI.

No, we won’t spend much time in St. John or Vieques. We’ll save those for another trip. There just isn’t enough time in a week to properly do those justice.

And yes, this is the plan for my next sailing trip coming up in November 2022. It’s going to be a guys trip on a sailing catamaran. Update: here’s the trip report.

Here’s what we are looking for and why this sailing itinerary might work for you:

  • Several longer days on the water with some chill days to mix it up

  • Two days of open, deepwater crossings, including sailing to St. Croix and back. In ideal trade wind conditions, you may not even have to make a single sail change.

  • Excellent opportunities to catch some mahi, tuna, and wahoo from your sailboat

  • Lots of schedule flexibility if the wind becomes too strong for comfortable crossings – remain in the protection of St. John, or head straight to Culebra

  • Off the beaten path – fewer charter boats visit these areas

  • Clearing customs is easy into the SVI with the CBP ROAM app, and not required for entering USVI from SVI (and there is no check out required). I describe how to do this below.

Flamenco Beach on the north side of Culebra - a global top 10 beach

Why Culebra and sailing to St. Croix?

I first visited the Spanish Virgin Islands in 2020 and was blown away. Laid back vibe, gorgeous beaches, and phenomenal snorkeling are some of the features drawing me back. I can’t wait to return and continue exploring!

Culebra (and Vieques) have been described as what the British Virgin Islands were about 30 years ago before they became popular. Better hurry before the word gets out.

If you have more than a week for this trip, consider adding a day or two at Vieques. Green Beach, Sun Bay, and Ensenada Honda are all worth a stop. If you can, navigate clockwise so you sail downwind with the current in your favor.

St. Croix makes the list for this sailing itinerary since it’s off the beaten path. I love checking out new places that might be out of reach to others. It also allows us the opportunity to get two awesome days of sailing in open water.

frenchtown marina in St Thomas
Frenchtown Marina near Charlotte Amalie in St. Thomas, one of the charter bases

Should you charter from Puerto Rico or St. Thomas?

My pick would be St. Thomas, but either one will work. A few things to consider:

Charter fleet availability

There are more operators, and sailing yachts available in St. Thomas, USVI. This means you might have a better chance of finding a suitable sailboat that fits your schedule (pro tip, let the Yacht Warriors help you!)


Consider where you are flying from. Does it offer a direct flight to San Juan, PR or St. Thomas? This might be enough reason alone to do one or the other.

Itinerary planning

You can pull off my itinerary below from either Puerto Rico or St. Thomas, but keep in mind leaving from Puerto del Rey will add about ~40 nautical miles roundtrip to the journey.


No problem from either with plenty of options available. I love visiting Costco in Puerto Rico, but the good news is that St. Thomas has a similar store – CostULess. Provisioning isn’t a factor that would sway me either way.

Sailing to St Croix planning
Cruising conditions for what you can expect when sailing to St. Croix

Why this itinerary design works:

I take you clockwise to take advantage of prevailing marine conditions, allowing for more comfortable cruising conditions with your crew

  • Easterly trade winds

    • The long fetch of the trades will produce wind swell that you want to avoid sailing/motoring directly into

    • Your crossing almost due south should be on a beam’s reach

    • Heading back north from St. Croix to Culebra will be a nice, broad reach with the swell on your quarter

    • Always check the forecast!

      • In stronger winds (15+ knots), even with a favorable wind direction, the larger swell could make things too uncomfortable for a crossing

      • Check my BVI weather and marine forecasting post for additional resources. It’s applicable for the SVI/USVI cruising grounds as well

  • Current: the prevailing current in this part of the Caribbean is 0.5 – 1.0 knots from the east/SE. This puts the current in your favor for the longer crossing from St. Croix to Culebra

  • When you travel back east to St. Thomas from Culebra, you will have an upwind slog (no avoiding it)

    • You should get some protection in the lee of St. Thomas from the long fetch of the trade wind swell

    • The current that you’ll have to fight will also be weaker closer to St. Thomas

Clearing customs between USVI and the Spanish Virgin Islands

OK, here’s what you need to do to make this go smoothly. It really isn’t that hard.

USVI to SVI (St. Croix to Culebra)

Clearing out of USVI

Checking out is not required. Hooray! Celebrate with a frosty Carib.

Clearing in to Puerto Rico (SVI)
  • If your crew is all U.S. citizens, make sure you have downloaded the latest version of the CBP ROAM app and previously completed your initial videoconference interview
    • You can do this in St. Thomas before you depart
    • Upon completion you’ll receive your Verified Traveler numbers.
  • Add your crew members in the app – have your passport or Global Entry info handy
  • Next, add your mode of travel – Pleasure Boat. You’ll need some info such as the vessel registration number and the CBP user decal number
  • Check with your charter company if you are uncertain. Most USVI based charter boats should be set up to use the ROAM app. The boat needs a DTOPS sticker
  • Technically, you need to be at the port of entry to report your arrival. This means anchored in Dewey, Culebra. Some people have been known to request the check-in when several miles out
  • Once you report your arrival, the CBP officer may get in contact, but they may also just clear you for entry
  • On rare occasions, they could still request that you show up in person.

If you are not U.S. citizens, you’ll need to visit the CBP office at the airport in Dewey (787) 742-3531)

Clearing out of Puerto Rico (SVI)

Again, nothing is required here.


Nothing is required to re-enter the US Virgin Islands from Puerto Rico.

Ram Head and Salt Pond Bay
Ram Head in the distance and the Salt Pond Bay anchorage

A week sailing the US and Spanish Virgin Islands                                      

Day 1: Stage for the crossing at St. John, USVI

Once you are underway, motor about 15 nautical miles east to pick up a National Park Service (NPS) mooring at Salt Pond Bay. This will be our staging point before we go sailing to St. Croix. It’s conveniently located about as far south as you can be on St. John.

There are five balls available. If they are all taken, you can work back west a bit to Great/Little Lameshur Bay where additional balls can be found. No anchoring is allowed in these bays.

Get settled in, enjoy your first night out of the marina, and grab a cocktail for a killer sunset. Consider a hike to Ram Head point. The trail can be easily found ashore at Salt Pond Bay.

If you have some time and want to do additional exploring, consider Coral Harbor around the corner for a day stop. It’s home of the well-known floating taco bar: LIME OUT.

Picturesque Dutch-inspired Christiansted in St. Croix
Some people believe Christiansted is the most beautiful Caribbean city

Day 2: Sailing to St. Croix: our first deepwater crossing south

Get an early start and get that fishing equipment prepped! Crank the sailing tunes. It’s time for some epic sailing and fishing.

From Ram Head, it’s about 32 nautical miles to the channel markers at the entrance to Christiansted. With 10-15 knot winds that should make for a 4-hour trip.

You have a couple options for anchorages once you arrive. Pay careful attention to charts and your cruising guide if you enter Christiansted.

  • Off the beach at Altona Lagoon – use this if you want to dinghy ashore and explore the island. It’s not recommended to use the anchorage marked behind Protestant Cay – much of this area is taken up by a large mooring field for full-time cruisers

  • In the lee of Green Cay, if you don’t plan to go ashore

  • Buck Island Reef National Monument – you’ll need to apply for a NPS permit to anchor here. Allow 5 days.

Fort Frederik in St. Croix USVI
Fort Frederik on the West End

St. Croix is considered the garden island and is known for it’s picturesque Dutch architecture. Many people believe Christiansted is one of the prettiest Caribbean towns.

For my trip plan, I will only stay one night at St. Croix, but feel free to add another day or two if you want to really explore the island. The Cruising Guide to the Virgin Islands has some recommendations for a day tour. Cars can be rented easily at Christiansted.

Frederiksted on the west end of the island is another option with excellent protection from the easterly trades.

If I had an extra day, I might even try and squeeze in a round of golf. The Buccaneer Golf Course is nearby and has many distracting views of the ocean!

Buccaneer Golf Course in St. Croix

After lunch, shopping in Christiansted, and some history at Fort Christiansvaern, I would move our yacht to the Buck Island Reef and spend the night there in solitude.

Get to the NPS site early enough to take advantage of the famous snorkeling at the Underwater Trail inside the lagoon.

If you’re lucky, you’ll have some fresh mahi fillets to whip up into fish tacos. Could you ask for anything more??

Beach at Buck Island
One of the beaches at Buck Island, looking back towards St. Croix
Heading through the channel on our way to check in at Dewey
Heading through the channel to Dewey, Culebra to get checked in

Day 3: Let’s go visit the Spanish Virgin Islands

OK – this is the last day I’ll get you up early.

Today is a bit longer than the last, but the sailing might even be sweeter, so it’s worth it. From Buck Island, it’s about 48nm to the channel entrance to Ensenada Honda (Dewey). Plan for 6-7 hours on a broad reach.

It’s also another great day for fishing!! If you are serious about it, you can veer more to the north and pick up the South Drop. Lower your sails and motor the rest of the way to Culebra, zig zagging across the drop in 200-600 feet of water. Get that gaff ready for a monster wahoo.

Bajos Grampus (Grampus Banks), about 2nm SE of Culebra, is another fishing spot worth checking out. It’s a couple sea mounds that rise from ~70 feet to about 15 feet from the surface. A lot of fish can be found on them. Test your hand here with some bottom dropping. If you’re a free diver, this is a great place to search for lobster.

Once in Dewey, anchor in 15-20 feet of water between Cayo Pirata and the town dock. Complete the clearing in process (described above).

If you want to grab a bite for dinner, you can remain anchored close to town. There are plenty of options within walking distance from the dock. It’s also a good time to provision fresh supplies if you need it.

Ensenada Dakity in Culebra
Ensenada Dakity anchorage in Culebra

If I had time, I would move to the moorings at Ensenada Dakity, the reef anchorage near the channel entrance. Here, you are exposed to the trade winds, but the reef provides excellent protection from the swell.

Read more about my top 5 favorite Culebra anchorages here.

In Dakity, be careful of the front row or mooring balls, it can get quite shallow.

Cayo Luis Pena
Cayo Luis Pena, viewed from the south

Day 4: Explore the Cayos west of Culebra

It’s time for some snorkeling and scuba diving.

The Cayos to the west of the main island of Culebra provide excellent opportunities for exploring the brilliant underwater marine life of the SVIs.

Take your pick or snorkel sites. Much of this area is part of the Culebra National Wildlife Refuge – designated such to protect seabird and turtle species. Activities such as fishing are prohibited and the islands can only be explored from sunrise to sunset.

Check your Puerto Rico cruising guide for details on the anchorages. It’s a combination of day anchorages and Department of Natural Resources (DNR) mooring balls. For some of these it’s OK to stay overnight.

Cayo Luis Pena is the largest island. It has a great white sand beach on the northern side and a hiking trail that runs to the southern part of the island.

Culebra Spanish Virgin Islands sunset at Playa Carlos Rosario
Killer sunset over the Cayos to the west of Culebra from one of our recent trips

For overnighting, I’d recommend the moorings at Carlos Rosario beach (unless there is a strong northerly swell running). It’s a perfect place to enjoy an unobstructed sunset over the Cayos to the west. Technically they are day use only, but I haven’t seen this enforced.

Our Lagoon 46 charter yacht at anchor at beautiful Flamenco Beach
Anchored our Lagoon 46 charter yacht on a recent trip right in front of the beach

Day 5: Beach day at Playa Flamenco

Today is a beach day, and we are going to chill at world renowned Flamenco Beach.

We have two options to get there. We can hike right from Carlos Rosario (check out my post on the Spanish Virgin Islands where I talk more about the hike) or better yet, we are going to anchor right in front of the beach.

To do this, you’ll need settled weather. Make sure there isn’t a northerly swell and ideally there will be <15 knots blowing with the easterlies. Also confirm this area isn’t redlined by your charter company.

You may have seen pictures of the beach with abandoned tanks the U.S. Navy used to use for target practice. Well, that’s Flamenco.

The beach setting is stunning and I will be content to relax with some cold ones and my toes in the sand. There are several food stalls that sell cheap beer and snacks on the eastern end of the beach.

Flamenco is a day anchorage only because you don’t want to be caught here if conditions turn unfavorable.

Raise your anchor and continue east around the northern Culebra to Culebrita. If you thought Flamenco Beach was awesome, wait until you see Playa Tortuga.

Make sure to stay overnight at Culebrita in settled conditions only. Otherwise you might be in for an uncomfortable night on a mooring ball. If the weather looks iffy, pick up a free mooring ball at Bahia de Almodovar (Las Pelas) behind the protection of the reef.

You can return to Culebrita the next morning.

View of Culebrita, one of the Culebra anchorages

Day 6: Explore the gem of the Spanish Virgin Islands – Culebrita

I talk a lot about Culebrita in my Spanish Virgin Islands cruising guide, so check that out for all the details including a hiking map.

I would plan to spend the entire day here. Hike to the lighthouse and visit with the goats for panoramic views of the neighborhood. Snorkel the nearby reefs. Check out the jacuzzis on the north side of the island. Or just sit and relax under a coconut palm on the white sand beach.

If you’re feeling adventurous and the conditions are settled, take the dinghy to explore Cayos Geniqui about a mile to the north. Or, closer to the anchorage, visit the dive spot marked on charts near Cayo Botella.

Magens Bay USVI in St Thomas

Day 7: Back to St. Thomas for our last day

This is somewhat of a free day – we just need to be anchored close to our marina for check out procedures the next day.

Here’s what I would do. I’d get an early start and head to the famous north drop for a last bit of deepwater fishing (assuming the trades aren’t blowing too hard).

For a quick lunch stop, we’ll pull into the bight at Magens Bay, home to another well-known beach. You can anchor close to shore. If you have time, dinghy to the beach to check out the local action.

Ashore you’ll find a perfect white sandy beach and Magens Point Bar and Grill for a couple of cold ones. If there are cruise ship passengers in the area, you might want to stay away!

After lunch we’ll head to Water Island for our final overnight anchorage. Allow yourself at least 1.5 hours to motor over there. If it’s crowded use Lindbergh or Flamingo Bays as back ups.

Ashore, Dinghy’s Beach Bar and Grill is an excellent choice to enjoy a final Caribbean sunset and celebrate a great trip with friends or family.

Thanks for reading my post about sailing to St. Croix and making it all the way to the end! If you enjoyed it, please subscribe or check out some of my other articles, like this one about my Top 5 Culebra Anchorages.