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.

Sailing from Key West to Dry Tortugas: What to Expect?

Sailing from Key West to the Dry Tortugas

A trip to the Dry Tortugas should be on everyone’s bucket list. History, seclusion, and pristine natural beauty are top reasons to go.

Each year, this National Park only gets around 55,000 visitors – most of them arrive by daily ferry aboard the Yankee Freedom. Some visitors also arrive by exclusive sea plane tours.

But there is a better way to visit! Take a private boat to the Dry Tortugas enjoy the multi-day adventure. Don’t have one? Charter a yacht as a bareboat or crewed charter instead.

There didn’t use to be many options for crews wishing to bareboat charter a sailboat from Key West to the Dry Tortugas. However, recently Florida Yacht Charters has partnered with the Moorings and maintain a Key West base. The cruising grounds to the Dry Tortugas are now available to us all!

I took advantage of this last year to during a 5 day adventure to go boating to the Dry Tortugas and back. It was an incredible trip with several of my closest friends. You can check out the details on my trip report post.

Planning on sailing from Key West to the Dry Tortugas? Here’s what you should know:

Drone shot of Garden Key and Fort Jefferson at sunset
The anchorage at Garden Key | We were one of two boats on this visit

Key West charter companies

If you have a private vessel – you are all set. If not, the good news is there is now at least one fleet that serves these cruising grounds out of Key West. The fleets are not huge, so make sure you plan in advance.

Florida Yacht Charters / Moorings

Florida Yacht Charters partners with the Moorings. They keep their yachts at either Oceans Edge Resort & Marina or at Stock Island Marina Village.

Pool Dock at Stock Island
Our catamaran at the pool dock at Stock Island Yacht Club

Other charter companies

The Navtours is partnered with Dream Yacht Charter but they have since closed the base. I believe they set it up as a temporary base during Covid.

You may also want to check out Calypso Sailing – they have several bases in the Keys and last reported they have three vessels for charter.

Squalls near Dry Tortugas
Year round you can expect to dodge an isolated squall or two

When should you go boating to the Dry Tortugas National Park?

I did this trip in August…and I would not recommend boating to the Dry Tortugas this time of year (doable maybe if you have reliable air conditioning aboard). South Florida is then very hot and the wind is also at it’s weakest and most variable. I slept on the catamaran trampoline every night it was that bad!

I think the Spring or early Fall are the best time to take a private boat to the Dry Tortugas. Why?

  • Less risk of tropical mischief

  • The heat is less intense and the weather is more settled

  • There is less risk of cold fronts which can barrel down with intense winds and squalls

  • Fishing in the fall as the water cools offers great chances at catching wahoo along the drop

Weather is the biggest factor to plan for. You want your best chance of a settled weather window. Aside from the anchorage at Fort Jefferson, there are really very few protected anchorages along this route.

Sailing from Key West to the Dry Tortugas
Arriving at the Dry Tortugas on our third day of the trip

How many days to plan for on your boating trip?

Unless you have a speed boat, I think the minimum number of days to plan for is a week. Here’s what that sailing itinerary looks like:

  • Day 1: arrive to Key West and overnight on your charter boat in the marina

  • Day 2: early am departure for Boca Grande. If you have time, grab a mooring ball for some snorkeling at one of the Florida Keys National Marine Sanctuary sites along the way: Western Sambo, Eastern/Western Dry Rocks, or Sand Key are good options.

Marquesas Keys sunset
Sunset over the Marquesas Keys
  • Day 3: sail the rest of the way to the Dry Tortugas and explore Fort Jefferson at Garden Key after most of the tourists have left for the day on the ferry.

  • Day 4: head over to Loggerhead Key for the day. Snorkel the Windjammer wreck. Return to Garden Key in the evening (you aren’t allowed to stay overnight at Loggerhead).

  • Day 5: early am departure to head back east. Overnight anchorage at the Marquesas Keys.

Key West anchorage behind Wisteria Island
Fish tacos at Garbo's
Fish tacos and a cold beer at Garbo's
  • Day 6: final leg back to Key West. Anchor close to downtown for some nightlife or spend the night back in the marina.

  • Day 7: checkout and travel day.

Dry Tortugas sailing route
Our sailing route - we made a stop at the reef and did some fishing along the drop
Fort Jefferson at the Dry Tortugas National Park
Exploring Fort Jefferson in the evening after the crowds have left for Key West

Sailing route from Key West to the Dry Tortugas

How far is the Dry Tortugas from Key West?

It’s approximately 80 nautical miles to the Dry Tortugas from Key West. If you are on a sailing charter vacation, plan for two days to get there and the same for the return. Yes, that can be done with a very early am departure, but don’t plan on checking out until mid morning. You know the drill with those check-out briefings.

It’s a great sail! The water is beautiful and the fishing is excellent.

With prevailing winds, you are most likely to have a downwind sail on the way there. Returning to Key West, you might be beating to windward and it might make sense to throw in the towel and motor.

As far as planning guides go, I picked up a copy of the Water Way Guide for the Keys. We also relied heavily on Garmin Active Captain for anchoring advice.

Water Way Guide Florida Keys (Amazon)

This is a useful guide to help plan your trip to the Dry Tortugas or elsewhere in the Florida Keys. Aside from navigational info, there is good discussion about activities to enjoy in each area.

Anchorages along the route

Main anchorage near downtown Key West

I like this anchorage at the end of the trip. Celebrate your final night and share stories about your adventures boating to the Dry Tortugas during a night on the town.

Boca Grande Key

Boca Grande is next up. In settled conditions, you can anchor in ~10 feet to the west of the popular beach (Boca Grande – 2 on Garmin Active Captain). You will swing some on the tide here as it flows between the Gulf of Mexico and the Gulf Stream at about 1 knot.

You can also anchor further up the channel that leads to the interior of the key, but be prepared for 180 shifts and swings on the tide.

Boca Grande Key Sunset
Great sunset over the Marquesas Keys as we anchored at Boca Grande

Marquesas Keys

The final anchorage before you reach the Dry Tortugas (and you still have about 50 miles to go) is the Marquesas Keys. It is less protected than Boca Grande, so keep that in mind if you are planning around some weather events.

Anchor within a few hundred yards of the beach. If the bugs are bad, you can venture farther out – look for the Brown Pelican anchorage on Active Captain which is about a mile offshore.

king mackerel near key west
Good sized king mackerel we hauled in using an Iland Ilander lure
Little tunny caught in about ~40 feet of water

Fishing on the way to the Dry Tortugas

You have great chances at catching fish boating to the Dry Tortugas. Depths range from 40-60 feet along the way – expect to catch king mackerel, little tunny, and barracuda.

I also like the idea of fishing the drop which will take you on a slight detour south if you can afford the time. Here you’ll have better chances of landing tuna, mahi, and wahoo.

There are also several spots to bottom drop, such as at Rebecca Shoal – here you have decent chances of hooking snapper and grouper.

Before you enter the park boundaries, make sure you stow away your equipment. Park rangers also ask you to report any catch that you are bringing into the park. You can do this on Channel 16.

Dodging lobster trap buoys

For me, the most frustrating part of this sail is the obstacles created by the lobster trap buoys. They are everywhere and you will find them along the length of the entire route. Perhaps this was because I visited at the start of lobster season (early August through March), but I’ve heard they are out there year round.

Unless your yacht has excellent visibility from the helm station, you should plan to post a bow watch to help you identify them. Unfortunately, frequent course adjustments was required for us. Not fun!

If you really want to avoid dealing with some of them, your only option is to venture farther south to the drop.

Thanks for reading my post about sailing from Key West to the Dry Tortugas 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 recent trip report sailing to the Dry Tortugas.

Bars & Restaurants Closed for 2022 BVI Hurricane Season

2022 BVI bars and restaurants closed for hurricane season

Many popular British Virgin Island establishments close for BVI hurricane season as yacht charter crews wait out potential weather disruptions. It also serves as a welcomed break for employees. The BVI hurricane season where tourism slows down peaks in August and September.

Most businesses will be back open by middle to late October, as the greatest threat of hurricane season in the BVIs has peaked.

Here’s a list of some bars and restaurants that closed for the 2022 BVI hurricane season and re-opening dates, where available.

📸 source: Saba Rock

North Sound & Virgin Gorda

  • Bitter End Yacht Club: re-opening October 19th
  • Saba Rock: re-opening October 17th
  • Leverick Bay: while the upstairs restaurant is closed, Jumbie’s is expected to remain open
  • Nova at Oil Nut Bay: re-opening October 8th
  • Blunder Bay, North Sound Bistro: unclear if they are currently closed, but they are expected to be open in October


  • Sugar Mill: re-opening October 16th
  • Brandywine Estate: re-opening September 14th
  • Indigo Beach House: re-opening October 15th
  • Quito’s: re-opening
  • Elmtones: re-opening late October or early November

Other BVI Islands

  • Cooper Island Beach Club: re-opening October 21st
  • Pirate’s Bight at Norman Island: re-opening October 1st

Bareboat Charter Guide for Beginners: How to Take Your First Sailing Vacation

Virgin Gorda Sound sunset with Saba Rock in the background (Pre-Irma)

Photo: spectacular evening in North Sound, BVI on our first bareboat yacht charter trip

Why go on a bareboat yacht charter trip?

To me, there is no better vacation than a bareboat charter on your own sailing yacht. It has everything I’m looking for – sailing, saltwater, unbelievable surroundings, a new adventure each day, deep sea fishing, good food, fun with friends/family, and epic sunsets.

It’s not for everyone, but if this appeals to you, once you try it you will never want to go back to your old vacation ways. As soon as we finish a bareboat charter trip, I’m already starting to think about the next one.

Forget those touristy excursions. Get away from the crowds and access amazing places other people can’t reach. Learn to sail, understand what it takes to go on yacht charter trip, and create your own memories and adventures to last a lifetime. If you haven’t been before, it’s not as hard as it may seem.

Look forward to other sailing destinations such as the British Virgin Islands, Exumas Bahamas, Spanish Virgin Islands, Dry Tortugas, Greece, and Tahiti.

In this bareboat charter guide for beginners, I’m going to tell you everything you need to know to give you the confidence to start planning your first trip. Let’s get started, there is not a moment to lose!

Anchorage in Anegada at Setting Point
On our bareboat charter yacht at Anegada, BVI back in 2018

Four ways to go on a yacht charter trip

A bareboat charter isn’t the only way to go on a yacht sailing vacation.

Bareboat charter

This is what my article focuses on – you serve as the captain, supply the crew, make provisioning arrangements, and decide where you want to go. The charter company will qualify your sailing experience to make sure you have a safe and fun trip.

Crewed charter

This is a great option if you want to decide if these types of trips are for you. You choose a yacht that comes with a dedicated captain and chef/hostess.

It’s the “all-inclusive” option. They will cook gourmet meals for you, mix you drinks, and tailor a sailing itinerary to your preferences. The yachts usually come with a wide variety of water toys.

Keep in mind, as you might expect, this is the most expensive option.

Bali 5.4 helm station view
At the helm of a Bali 5.4 in the Exuma Bahamas

Captained charter

You book this type of trip with one of the charter companies, and they help to provide you with a skipper. Choose also to add on a chef.

While this sounds similar to a crewed charter, you don’t know exactly who will be assigned to your trip. The experience you have will be less predictable and the customer service is perhaps not quite as top notch.

By the cabin charter

This type of shared charter let’s you book one or two cabins. You’ll have strangers aboard that you share the charter trip with. It may be offered by the charter companies or by one of the many crewed options available.

What is a bareboat charter?

A bareboat charter simply means that you rent a boat from a charter company for a defined period of time. Most importantly, the arrangement does not come with a captain, crew, or provisions – it is up to you to provide those things.

On your charter, you have the freedom to do whatever you’d like (within reason or course) during your trip – sailing, snorkeling, fishing, etc. These are more of my favorite boat trip activities.

Fowl Cay in the Exumas
Lunch snorkel spot in the Exumas on our 2021 yacht charter trip

Skills that you need for a bareboat charter

You do not need to be sailing certified to charter a sailboat. If you have substantial sailing experience on similarly sized yachts, you can provide a sailing resume to qualify with the various charter companies.

We’d recommend going to sailing school and getting certified anyway. We took three courses through the American Sailing Association:

ASA 101: Basic Keelboat Sailing – This is the introductory course for sailing. We had no sailing experience and wanted to learn when we were living in San Diego.  We also joined a local sailing club to practice our skills once or twice a month in San Diego Bay. The course is two days and usually completed over a weekend.

ASA 103: Basic Coastal Cruising – Builds on the basics you learned in 101 and further develops your seamanship.

ASA 104: Bareboat Cruising – Teaches you more about a boat’s systems and other skills such as anchoring, docking, provisioning, and advanced sail trim.

It’s worth nothing that ASA 103 and 104 are often offered as a combo course. We suggest taking 101, getting some practice in, and then if you decide sailing is for you, go take the 103/104 combo course. The 103/104 combo can also be done over a weekend.

If you have some sailing experience and just want the resource, you can purchase ASA’s book for the bareboat course.

The SmarterCharter book is also a great practical guide for skills specific to bareboating. There is also a monohull version.

Catamaran downwind sailing on a bareboat charter trip
Easy downwind sailing in 10 knots


Do you need to know how to sail? No! You can always hire a skipper or take a crewed charter for your first time if you want to test the waters first with this type of trip. The skipper can take you places that you might not have the confidence to go as a beginner.

Another option is to charter a motor yacht. Marine Max specializes in power catamarans.

You do not need to sail the whole time. One trip we had very light winds on several days, so we just motored. You will have plenty of fuel, even if you motor the majority of the time. You shouldn’t need to worry about stopping at a marina to refuel.

Anchoring and mooring

Do you need to know how to anchor? Yes! This is a skill that you should be comfortable with. Even if you only plan to tie off to mooring balls, consider a situation where all of the mooring balls are taken. In this case you may be forced to anchor.

We’d recommend picking a first destination such as the BVI where you can pick up a mooring ball at most popular anchorages. Familiarize yourself with how to reserve Boaty Ball moorings in the BVI, if necessary. This will keep the stress down for your first trip – you shouldn’t need to anchor overnight. Practice anchoring at a day lunch stop, such as Sandy Spit near Little Jost Van Dyke in the BVI.

On our first trip we did just this – we used mooring balls. Now that we have plenty of experience, we seek out secluded anchorages and enjoy anchoring overnight.

This video from Sailing La Vagabonde provides a good overview about how mooring balls work.

Dodging squalls on the way to the Dry Tortugas on a bareboat charter trip
Getting ready to deal with an isolated squall


For a complete guide to BVI weather and marine forecasting, check out my post here.

Plan to take your first trip during periods when settled weather can be expected. For the Bahamas and the Caribbean this means April-May and late November. Tropical systems are unlikely. The trade winds blow consistently out of the east at 10-15 knots – perfect conditions to practice your seamanship.

Plan to monitor weather conditions for the week leading up to your trip. This will help you to notice patterns that could affect your trip. Marine weather forecasts are available online from resources such as the National Weather Service. Your charter company will provide more detail on how to monitor weather during your charter.

If sailing in the Virgin Islands, know if a ground swell is forecasted. They are common between November and April. Make sure you are check the forecast since it could have an impact on your itinerary. Any anchorage exposed to the north will be unusable if a ground swell is running. The NWS Marine Forecast will include information about ground swells. They are very well forecasted.

You should also be familiar with how local conditions such as tides and island geography can affect your boat – such as being backwinded (this is more important if you plan to anchor).


ASA 104 should prepare you well to manage the boats systems. The most important part is making sure you are monitoring fuel, water, and battery levels. Ask lots of questions during your boat briefing and make sure you are comfortable working the electrical system by yourself. For example, they will explain how to charge the batteries and turn on the AC system.


You’ll want to understand how to read the water color, read charts, and plan a route. Pick a destination like BVI that has easy point and shoot navigation.


Docking can be stressful and intimidating. You can read all about it, but unfortunately the only way you get better is by practicing.

Here’s the solution – for your first trip, request assistance from the charter company when leaving the marina. They can help with the dock lines and also pilot the boat out for you. Use them! It will keep the stress down. At the end of the trip, reach them on the radio and they will send someone out in a dinghy to pilot the sailboat back in.

Practice docking on your own terms under ideal conditions.

Our first bareboat charter trip in virgin gorda sound
Aboard a 37 foot monohull in North Sound, BVI - the trip that started it all for the Yacht Warriors

What to consider when choosing a yacht charter boat

On our first boat trip, the one that started it all, we went out on a 37 foot, 2 cabin monohull. Every trip we’ve taken since has been on a ~45 foot 4 cabin, 4 head catamaran.

But, pick what you like! There is no right answer here. A couple things to consider:

Catamaran vs. Monohull

This can be a fiercely debated topic amongst seasoned sailors. For a sailing vacation, I believe a catamaran is the way to go. I write about it in more detail here. And if you want a complete review of a catamaran with lots of pictures, check out my thoughts on the Bali 5.4.

We enjoy having more space, a salon above the waterline, and the stability two hulls provide. I also find that I can maneuver a catamaran more easily because it has twin engines.

We also tend to go vacation with a crew of 8, and this works well with the space cats provide.

As far as sailing performance goes, monohulls tend to sail closer to the wind and can be faster than the catamarans that you’ll find in bareboat fleets. They will also keel over, which some people enjoy.


After you’ve picked a type of boat, I recommend that you choose the newest one that you can afford. Older yachts tend to have a greater chance of a breakdown. Your charter company will do their best to fix any issue, but it can definitely disrupt your plans (speaking from experience here!).

Spending a bit more on a newer sailboat is a good insurance policy.


Sometimes it will just come down to what’s available. Don’t sweat it. We’ve sailed on Lagoons, Leopards, and Balis. You’ll have a great time on any of them.

One feature we love is a fly bridge – essentially a common area up top that includes the helm station where everyone can hang out while cruising. We find that this is more fun than a separate area where the skipper operates the boat.

Bali 5.4 in the Exumas on a bareboat charter trip
Plenty of room for the whole crew on this Bali catamaran

Charter Company

We’ve used many different charter companies over the years. In the British Virgin Islands, you have many to choose from. In other sailing destinations, you may only have one or two options.

I will say after dealing with many larger operators, customer service can sometimes leave much to be desired. I’ve heard much better things about smaller independent operators. They may not have quite the yacht variety, or availability, but there are always tradeoffs.

Each of them has different bases or marinas they operate from – some will have specific amenities that might appeal to you.

Reputation for quickly addressing any maintenance issues should also factor into your decision.

painkillers at the soggy dollar bar in white bay jost van dyke
Lady crew members lined up with painkillers at the Soggy Dollar Bar in BVI

Picking your crew

Picking your crew members may be the most important decision of your entire trip. Who you decide to take with you matters. We have lots of friends, but we wouldn’t want to spend 8 days on a boat with all of them (no offense friends!).

Choose wisely. Will they get along? Are they flexible if plans change? Would they be OK skipping a shower if the water runs low? Are they willing to help out (with cooking, cleaning, etc)?

How long should I plan the yacht charter trip for? 

We like to do trips that include 8 nights on the boat. The first night is usually a later check in and spent overnight in the marina after a day of travel. That makes for 7 full days of exploring and adventure on your sailing charter.

You can also consider staying in a hotel for your first night, but we like to stow away provisions and get familiar with the boat. It also allows for an earlier departure on your first full day – don’t waste valuable cruising time in the marina! 


Most charter companies can provide a provisioning service. Coordinate with your crew for meal planning and make your selections. The food and beverages will be aboard your sailboat when you arrive, what joy!

Check out our post on how to get the crew organized to help with provisioning planning.

You can also do the shopping yourself depending on the destination – Key West and the Spanish Virgin Islands are good candidates.

For a first time bareboat charter, keep it easy and let one of the provisioning services handle it for you.

We always plan for big breakfasts – eggs, bacon, and hash browns. Start your day right!

Lunches we keep simple since we are usually on the move or exploring ashore – sandwiches and chips work great.

For dinners, consider how many meals you’ll plan to eat ashore at beach restaurants. The other nights, simple is always better. Pasta, burgers, and tacos are some of our staples. Spend less time in the galley and more time soaking up that Caribbean sunset.

Palm Cay sunset, the Exuma bareboat charter base
One of the marina bases that you might use - this one in the Exumas

What is the check-in and check-out process like? 


You will typically board your boat in the evening. Get comfortable, and in the morning, a representative from the charter company will meet you for the boat briefing. Here’s what they’ll cover – I talk more about what to expect for the boat briefing on this post. If you sign up for my free newsletter, I’ll send you a pdf version of my Boat Briefing Checklist that you can print and take with you on your first trip.

  • Cruising grounds – they can give you advice on where to go and what areas may be off limits. 
  • Boat systems and operation – you’ll do an inventory and cover all you need to know about the sailboat’s systems and sailing equipment. Have a list of questions prepared in case they miss something.
  • Safety – such as where the life jackets, life raft, plugs, and emergency tiller are located. You should also cover radio procedures if you need a refresher.
  • Communications – how to get in touch with the charter company if you have a repair issue or what to do when you are ready to return to the marina.


Check out is usually mid morning on your last day. You can either return to the marina the night before, or stay in an anchorage nearby.

Sometimes they ask you to visit the fuel dock, but you can also pay the charter company to handle this service for you. They might do another inventory with you, but usually you just need to disclose if anything is broken or missing.

The Indians, BVI
Popular snorkel spot: The Indians in the BVIs

Charter destination for your first trip: British Virgin Islands

There is no better sailing trip for beginners than the British Virgin Islands. Here’s why:

  • Idyllic Caribbean surroundings – numerous tropical islands that rise sharply out of the ocean. Plenty of protected anchorages. Coconut palm lined white sandy beaches. Great snorkeling and fishing. What else do you need?
  • Settled weather – you can expect steady trade winds out of the east year round. If you avoid the summer months when tropical systems can develop, there is little risk of a major weather disruption.
  • Easy navigation – there are few navigational hazards and you can usually see the islands you are navigating towards.
  • Mooring balls – there are plenty of well maintained balls available, making it easier for beginners.
  • Well established bareboat yacht charter industry – lots of operators, a deep bareboat charter fleet, plenty of restauraunts that serve boaters, and many services to help make your trip easy.

If you have a cruising ground close to home that offers some of these same features, that could be a great option too!

North Sound in Virgin Gorda, BVI

First time BVI bareboat charter sailing itinerary

We’ve visited the BVIs four times now, and every time our itinerary gets a little bit better. Here’s what I would do on a first time visit. (update – here’s a more in depth post about a first time BVI sailing itinerary).

You can also visit this link to see my other articles I’ve written about the British Virgin Islands. My FAQs will also address the most common questions.

If you want more information about how to navigate to Anegada and what to do there, check out this write up.

Travel day
Day 1: Travel day
Arrive, get settled in, and stow away your provisions. Familiarize yourself with the boat's systems if you'd like. Crack a beer - you've made it!
Travel day
Cooper Island Beach Club
Day 2: Cooper Island
Plan for an easy, short sail on your first full day on the water. Cooper Island Beach Club is a perfect stop. Grab a mooring ball and head ashore to enjoy the facilities, bar, and restaurant. Arrive early - the mooring balls fill up quickly! You may also enjoy a snorkel at Cistern Point to the south.
Cooper Island Beach Club
Devil's Bay at the Baths, a top BVI Beach
The Baths & North Sound
Day 3: Baths & North Sound
Get an early start and sail up the Sir Francis Drake Channel. Stop for lunch at The Baths, a must see visit. Swim ashore and hike through the monstrous boulders to Devil's Bay.

Round Virgin Gorda and enter North Sound through the well-marked channel. There are many places to choose from including the Bitter End Yacht Club, Saba Rock, and Leverick Bay. Plenty of mooring balls are available.
Devil's Bay at the Baths, a top BVI Beach
The Baths & North Sound
Sunset at Setting Point in Anegada
Anegada & Setting Point
Day 4: Anegada
Some will say to avoid Anegada if you are a beginner, but I disagree. The channel is well marked and it is only a couple hours sail offshore. Check with your charter company. Anegada is a low lying, coral island making up part of Horseshoe Reef - the 4th largest barrier reef in the world. Rent a car and visit the spectacular beaches on the north shore. Enjoy a freshly caught spiny lobster dinner at one of the many Setting Point restaurants.
Sunset at Setting Point in Anegada
Anegada & Setting Point
sunset at Cane Garden Bay in the BVIs
Cane Garden Bay
Day 5: Cane Garden Bay
Head back south and sail counter clockwise around Tortola. Monkey Point at Guana Island is a great snorkel lunch stop. Cane Garden Bay is a picturesque spot with lots of room and plenty of mooring balls. This is a great opportunity to head ashore and shop for additional provisions if you need them. There are lots of restaurants to choose from if you want to eat ashore.
sunset at Cane Garden Bay in the BVIs
Cane Garden Bay
Sandy Spit BVI, a top 10 BVI beach
Sandy Spit
Day 6: Sandy Spit & Great Harbour
Make your way north and try your hand at anchoring near Sandy Spit. This is a fun day spot. Dinghy ashore for a picnic. Great Harbour at Jost Van Dyke is home to the famous Foxy's Bar. Enjoy some late night live music and dancing. Over the weekend, they have a famous Beach BBQ.
Sandy Spit BVI, a top 10 BVI beach
Sandy Spit
swimming at white bay jost van dyke
White Bay & the Soggy Dollar Bar
Day 7: White Bay & The Soggy Dollar Bar
Get an early start to grab a mooring ball on the east side of the bay. Check with your charter company to make sure it is not off limits. Enjoy a full day of beach bar relaxing and fun. The Soggy Dollar Bar is world famous for its invention - the Pain Killer. If you're a beginner, I don't recommend anchoring at White Bay. Stay at Great Harbour and dinghy over, or walk.
swimming at white bay jost van dyke
White Bay & the Soggy Dollar Bar
The Indians, BVI
The Indians & the Bight
Day 8: The Indians & the Bight
Pass nearby St. John, USVI and head for a lunch stop and snorkel at The Indians. Make a loop around the rock formations and enjoy the abundant sea life. Stay overnight at the Bight and join the party at Willy-Ts, the famous floating pirate ship bar and restaurant. The Pirate's Bight restaurant is also a very good choice for a last night send off.
The Indians, BVI
The Indians & the Bight
Travel Home
Day 9: Travel Home
Leave early enough to motor back to the base to comply with checkout procedures. Radio your charter company on your way back in if you'd like help docking the boat.
Travel Home

Thanks for reading my bareboat charter guide for beginners 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 secret anchorages in the BVIs.

UPDATE 6: Dry Tortugas Re-opens to Visitors After Hurricane Ian

Dry Tortugas National Park takes direct hit from Hurricane Ian

On Tuesday evening, September 27th, major Hurricane Ian made it’s first US landfall, marking a direct hit to the Dry Tortugas National Park in Florida.

The storm had been strengthening steadily after crossing western Cuba, with sustained winds of 120 mph as the eyewall passed directly over Garden Key and Loggerhead Key. Heavy rains and storm surge also directly affected all areas of the 100 square mile park.

Current status of Dry Tortugas Hurricane Ian storm damage assessment and re-opening

On Thursday, September 29th, National Park Service (NPS) staff began to assess storm damage with a flyover of the the main Dry Tortugas attractions, including Garden Key. It was noted that there was significant damage to the ferry docks and visitor boat slips at Fort Jefferson..

The NPS deployed the M/V Fort Jefferson on Friday, September 30th, with a team to further assess damage and commence clean up efforts.

Dry Tortugas National Park Re-opening Updates

  • Ferry service resumes on Monday, October 10th, as announced by the NPS
  • Limited camping spaces are now available
  • Park waters are currently open to private vessels, but the boat slips remain closed
  • As of Sunday, October 2nd, sea plane tours have resumed for visitors
  • The interior of Fort Jefferson is now open to visitors
  • If you plan to visit park waters by private vessel, keep in mind that many buoys and boundary markers might have been damaged by Hurricane Ian – they have not yet been inspected
Fort Jefferson damage from Hurricane Ian
Trees damaged by Hurricane Ian on Garden Key 📸 NPS
Clean up efforts underway at the boat slips 📸 NPS
Fort Jefferson days after taking a direct hit from Hurricane Ian in the Dry Tortugas
View of Fort Jefferson, looking south, taken from the flyover on Thursday, September 29th | NPS
Hurricane Ian damage to Fort Jefferson
Trees of the Fort Jefferson interior parade grounds sustained notable damage, stripped of their vegetation | NPS
Dry Tortugas National Park takes a direct hit from Hurricane Ian
Close up view of Hurricane Ian's eye, passing directly over the Dry Tortugas | Source: RadarScope

With a direct hit from the eyewall of Hurricane Ian, the NPS will make sure that key park features such as Fort Jefferson are deemed safe again for visitors before the Dry Tortugas National Park completely reopens.

Subscribe to the Yacht Warriors for updates on storm damage and Dry Tortugas re-opening dates.

Hurricane Ian Dry Tortugas before and after photos

Thanks to a tip from a Yacht Warriors follower, we can begin to identify some of the damage that may have occurred to the Dry Tortugas from Hurricane Ian. NOAA released some imagery taken several days after Hurricane Ian passed.

I compared some of the before and after imagery. Check it out below. My overall assessment? It doesn’t look like there was any major structural damage visible from satellite photos. Shifting of sand, damage to docks, and vegetation damage look like the biggest culprits.

Of course, a birds eye view is nothing compared to what the NPS will learn in the coming days with their crew on the ground.

Dry Tortugas and garden key before and after photos from Hurricane Ian
Notable changes are visible to Bush and Long Keys from Hurricane Ian storm surge | NOAA & Google Maps
Garden Key before and after photos from Hurricane Ian including Fort Jefferson
A zoomed in view shows some damage to the camping area and boat slips at Garden Key | NOAA & Google Maps
Dry Tortugas Garden Key ferry dock damage from Hurricane Ian
Some damage from storm swell to the Garden Key dock is visible, but many decking boards are still in place | NPS
Hurricane Ian before and after photos from Loggerhead Key in the Dry Tortugas
There are some visible changes to the shape of the sand bars at Loggerhead Key | NOAA & Google Maps
Close up before and after Hurricane Ian photos of Loggerhead Key
The only visible damage I could identify to Loggerhead Key is the dock on the east side | NOAA & Google Maps
Hurricane Ian damage to Loggerhead Key in the Dry Tortugas
Close up view of the damage to the Loggerhead Key docks from Hurricane Ian | NPS

History of Dry Tortugas and hurricanes

This is by no means the first hurricane to affect the park since construction of Fort Jefferson commenced on Garden Key in 1846.

Most recently in 2017, Hurricane Irma damaged a ~50 foot section of the moat wall and deposited large amounts of sand within the moat and piers. It’s worth noting that Hurricane Irma was not a direct hit – it passed ~90 miles to the east, at Cudjoe Key.

Damage to the moat wall from Hurricane Irma in 2017 | Source: NPS

Hurricane Ian continued to strengthen to a very dangerous category 4 storm with sustained winds of over 155mph. It made a second Florida landfall in the afternoon of Wednesday, September 28th, near Cape Coral, Florida.

If you want to learn more about the Dry Tortugas, read my post about sailing from Key West to the Dry Tortugas or my yacht charter trip report from August 2021.

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!).

5 Ways to Experience Norman Island, British Virgin Islands

Norman Island British Virgin Islands | 5 Ways to Experience

You can’t go on a BVI yacht charter without a stop at Norman Island in the British Virgin Islands. It’s a must for any BVI sailing itinerary.

So-called Treasure Island’s focal point, The Bight, is one of the largest and well-protected mooring fields in the British Virgin Islands. There are plenty of balls here – no need to race that other catamaran for the last one as you might be tempted to in some other BVI bays.

So what do I like to do at Norman Island? Check out these five activities for your next visit at Norman Island in the British Virgin Islands.

Willy T at Norman Island BVI
Willy T at anchor at its Norman Island BVI home

Jump off the top deck of Willy T

Yes, the William Thornton (Willy T) might be the most famous attraction at Norman Island, so it’s worth mentioning first. The original Willy T floating pirate ship bar was destroyed during Hurricane Irma in 2017. It now rests on the seafloor near Peter Island as an artificial reef and interesting snorkel site.

The Willy T crew found a replacement in Louisiana, outfitted her, and sailed her back to the British Virgin Islands themselves. It’s now back at anchor at it’s Norman Island home (after a short stint at Peter Island).

Jump in your dinghy and head over to Willy T for a rowdy evening (yes it can get that way!). Just read the Pirate Code that’s posted and you’ll understand why. Drinks flow and the food is actually really good.

Willy T Bar at Norman Island British Virgin Islands

On my last visit, my honor was at stake and I ended up beating a German professional soccer team in a pull up competition. Be prepared for anything!

And of course, make sure you join in the tradition of jumping off the top deck into the waters of the Bight. If you’re looking for something fancier, check out the Pirate’s Bight restaurant ashore and maybe go to Willy T after dinner.

A final tip: if you want some peace and quiet, grab a mooring ball on the other side of the Bight from the Willy T.

One of the beautiful bays you can access by trails on the south side of Norman Island

Hike the Norman Island trails for spectacular 360 views of the British Virgin Islands

Norman Island is actually private, but there are no issues going ashore (at least that I’ve heard). It’s owned by billionaire Henry Jarecki, who also owns the luxury eco-resort of Guana Island (another great place to anchor!). Several developments have been planned over the years, but nothing ever seems to get underway.

That’s good news for all of us that love this largely undeveloped, uninhabited island. One way to enjoy it? Check out the several miles of hiking trails. You can see them clearly on Google Maps satellite.

The easiest place to access them is behind the Pirate’s Bight restaurant. You can also dinghy ashore at Benures Bay to pick up one of the trails.

Most of the trails run along the ridge of the island, offering excellent views of the other BVI islands and the Caribbean Sea.

Keep your eye out for lost treasure that is still rumored to be buried on Norman Island.

Benures Bay Sunset at Norman Island, British Virgin Islands
Epic sunset from our yacht charter trip in 2018, we had the place all to ourselves

Soak in an epic sunset at Benures Bay

One of my favorite anchorages in the British Virgin Islands is at Benures Bay, on the north side of Norman Island. While there are several mooring balls here now, it’s still a great place to escape the crowds of the Bight.

Usually well-protected, it can be a bit rolly if the wind has a northerly component.

Drop the hook in the northeast corner and enjoy this bay by snorkeling, paddle boarding, or by accessing the trails ashore.

But by far the number one reason to visit Benures Bay: the sunsets over Sir Francis Drake Channel. You’ll have amazing, unobstructed view to the west as the sun sets over the Indians and St. John, US Virgin Islands. Grab a cocktail and enjoy the show.

Norman Island Caves British Virgin Islands
Approaching by dinghy for an afternoon snorkel at the Norman Island Caves

Search for treasure at the famous Norman Island Caves

This is one of the best, and most popular, snorkeling sites in the British Virgin Islands. It’s comprised of four caves on the other side of Treasure Point, just outside of the Bight.

There are two main attractions here: treasure lore and fish.

It’s rumored that a fisherman in the late 1800s once found a large stash of gold booty here that was dislodged during a storm, supposedly from the Spanish galleon Nuestra Senora de Guadalupe. True? I’m not sure, but it’s fun to believe it, especially when you’re exploring the caves. This book has all the details about the true story of Norman Island and Robert Louis Stevenson’s fictional tale, Treasure Island.

Norman Island Caves in British Virgin Islands
One of the four caves you can snorkel at Treasure Point

The marine life here also never disappoints. Expect to swim with hundreds of small fish, and the last time I visited we saw two octopus.

You can grab a National Parks Trust mooring ball here with your yacht, but I think it’s easier to grab your overnight mooring in the Bight and just dinghy over.

fresh mahi caught on a sailboat
Hauling in a mahi mahi on the south drop, caught with a purple Iland Ilander lure

Catch some mahi-mahi at the South Drop

Just over a mile offshore from Norman Island is the South Drop, where depths fall quickly from 100 feet to thousands. This underwater structure helps support abundant marine life from the upwelling of currents, bringing nutrients to the surface.

If you like fishing, this is the most convenient location in the British Virgin Islands to target some deepwater fish. We’ve hooked up on several mahi trolling over the drop and the nearby shelf area. Wahoo are good targets in the fall as the water temperatures cool, and tuna can also be caught year round.

south drop in the bvis
South drop visible just over a mile away from Norman Island | Navionics

Check out my BVI fishing tips for more advice on hooking fish on your next trip including tackle and lure recommendations.

With prevailing trade winds out of the east, I would head clockwise around Norman Island so you are sailing downwind as you fish. It will be much more comfortable for the crew.

Thanks for reading my post about Norman Island, British Virgin Islands! If you enjoyed it, please subscribe or check out some of my other articles, like this one about my favorite, top 10 BVI beaches.

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.

Top 7 BVI Webcams to Check in on the Action

If you ever find yourself dreaming of a yacht charter vacation, get your island fix by checking in on these BVI webcams from some of the most popular British Virgin Island institutions.

painkillers at the soggy dollar bar in white bay jost van dyke

Soggy Dollar Bar webcam

Thanks for checking out the list of BVI webcams. For more information on the British Virgin Islands, check out other articles and posts here.