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

East End on St Croix USVI

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

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

Think again.

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

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

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

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

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

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

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

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

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

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

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

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

Why Culebra and St. Croix?

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

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

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

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

Crown Bay Marina in St Thomas
Crown Bay Marina near Charlotte Amalie in St. Thomas

Should you charter from Puerto Rico or St. Thomas?

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

Charter fleet availability

There are more operators, and sailing yachts available in St. Thomas, USVI. This means you might have a better chance of finding a suitable sailboat that fits your schedule.

Logistics

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

Itinerary planning

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

Provisioning

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

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

Why this itinerary design works:

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

  • Easterly trade winds

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

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

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

    • Always check the forecast!

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

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

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

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

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

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

Clearing customs between USVI and the Spanish Virgin Islands

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

USVI to SVI (St. Croix to Culebra)

Clearing out of USVI

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

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

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

Clearing out of Puerto Rico (SVI)

Again, nothing is required here.

SVI to USVI

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

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

A week sailing the US and Spanish Virgin Islands                                      

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Buccaneer Golf Course in St. Croix

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

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

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

Beach at Buck Island
One of the beaches at Buck Island, looking back towards St. Croix
Town of Dewey at Culebra
The town of Dewey, Culebra

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

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

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

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

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

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

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

Ensenada Dakity in Culebra
Ensenada Dakity anchorage in Culebra

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

Read more about my top 5 favorite Culebra anchorages here.

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

Cayo Luis Pena
Cayo Luis Pena, viewed from the south

Day 4: Explore the Cayos west of Culebra

It’s time for some snorkeling and scuba diving.

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

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

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

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

Carlos Rosario sunset in Culebra
Killer sunset over the Cayos to the west of Culebra

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

Tank at Flamenco Beach

Day 5: Beach day at Playa Flamenco

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

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

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

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

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

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

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

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

You can return to Culebrita the next morning.

View of Culebrita, one of the Culebra anchorages

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

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

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

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

Magens Bay USVI in St Thomas

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

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

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

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

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

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

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

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

Is White Bay in Jost Van Dyke too Dangerous to Anchor Your Sailboat?

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

There might not be a more idlyllic British Virgin Islands experience than anchoring in front of the Soggy Dollar Bar at White Bay, Jost Van Dyke, swimming ashore, and ordering a Painkiller from the bar.

But for me, those days might be over.

Why?

It’s becoming an overcrowded anchorage with increasing amounts of reckless behavior from inexperienced “credit card captains”.

Many charter companies now redline this anchorage as an off-limits, no-go area.

White Bay can be dangerous for other non-man made reasons, but a prudent skipper can safely mitigate those risks.

Now let me be clear: I am not recommending you avoid White Bay and the beloved beach bars that line it, such as Coco Loco, Soggy, Hendo’s, and Ivan’s Stress Free Bar.

I just think there are better ways to experience this wonderful piece of paradise.

What is the White Bay anchorage like?

Why is White Bay becoming so popular?

Alternatives to anchoring at White Bay

aerial view of white bay jost van dyke
Overview of the White Bay anchorage with the east and west side

What is the White Bay anchorage like?

This famous British Virgin Islands anchorage is split in two – an east and a west side. The west side being the more popular crowded area in front of the Soggy Dollar Bar.

Narrow channels mark the entrance to each side, with a reef restricting safe access from anywhere else (although ill-advised skippers have been known to bypass the markers).

Inside the anchorages, it can get quite tight with little swinging room on a busy day.

Crowding leaves little margin for error. If a boat drags anchor it can quickly turn into bumper cars. Take this recent incident for example.

Video of unmanned 50 foot catamaran motoring around the White Bay anchorage.

Here’s what I think happened based on comments I’ve read about the incident:

  • Skipper and crew all went ashore and left the engines in idle, presumably to charge batteries (you should never do this!!)

  • A jib sheet was left improperly secured

  • At some point, the sheet became loose and began flapping in the wind as the sail unfurled from the wind

  • The sheet wrapped around the throttles and put the engines in gear

  • The cat was tied off to a mooring ball, and it motored in circles until it pulled out the screw, causing the incident you see in the video

It’s extremely fortunate that no one was hurt. I’ve often swam in those waters to and from the beach.

This isn’t the only accident that has occurred, just the most recent.

Here’s another two incidents that recently occurred, at the same time. The catamaran in the background anchored in the channel, realized the mistake, and then proceeded to foul the anchor chain with the channel marker.

The monohull appears to have grounded on the reef and is attempting to get pulled off by the dinghy.

Grounding in White Bay Jost Van Dyke
A grounding and another boat that fouled the channel marker
swimming at white bay jost van dyke
The action settles down by the evening at White Bay as the day trippers depart

So have I anchored overnight in White Bay on the west side? Yes, so how did I get comfortable with it?

  • Light winds were forecasted: 5-10 knots

  • No thunderstorms were forecasted

  • I had planned to leave for Great Harbour if it became too crowded

  • I visited in late May when White Bay is less busy than usual (although today that might not be the case)

Will I do it again? Probably not anymore. While it does thin out in the evening, I prefer not to deal with the daytime party madness.

White Bay anchorage at Jost van Dyke
Here's where I anchored in front of Hendo's on the west side on my last trip | Only two boats remained overnight, the powercat is on a mooring ball

Weather conditions that affect White Bay

Thunderstorms

If any thunderstorms are forecasted for the area, even an isolated squall, it’s best to avoid the anchorage overnight.

If a squall rolls in and you drag anchor, it’s very unlikely you will have time to get to the helm station and take action before being grounded on the beach or reef.

Northerly ground swells

While south facing, northerly ground swells from distant storms can still wrap there way around the west side of JVD and make the anchorage uncomfortable. If severe enough, these can also cause a similar condition where the anchor drags.

I talk more about this weather feature in my piece on BVI weather and marine forecasting.

Backwinding

If the easterly trades shift more into the NE, it is possible to get backwinded at White Bay. This isn’t a good situation since your yacht is already quite close to the beach.

Basically, strong trades (15+ knots) blowing over steep terrain can create a vortex where at the surface, you actually experience winds opposite of those that are prevailing. In this case, you could experience SE winds which could push you towards the shore.

If you don’t have enough swinging room (which is always a challenge in White Bay), you could ground on the beach.

Again, see my BVI weather post if you want to learn more.

View from the dock at Foxy's Taboo at Diamond Cay

Alternatives to anchoring at White Bay Jost Van Dyke in the BVIs

The great news: there are many!!

Utilize the mooring field at Diamond Cay near Little Jost Van Dyke

This would be my recommendation and the approach I’ll take next time I visit the BVIs (hopefully soon, it’s been 3 years!)

It’s easy to arrange for a taxi for a quick 15 min day trip to White Bay.

Staying here also allows you to kill two birds with one stone – you are a short hike away from the Bubbly Pool one of the most popular attractions at Jost Van Dyke. It’s a half mile hike. Bring your swimsuit to enjoy the pool at hightide as the waves crash through.

If you want a more laid back beach vibe, visit B-Line with your dinghy. Foxy’s Taboo is also a great option for a cocktail or dinner.

bubbly pool jost van dyke
Bubbly pool at Jost Van Dyke

Stay nearby at Great Harbour or Little Harbour

Next door, Great Harbour and Little Harbour are also safer alternatives.

Great Harbour now has Boaty Ball moorings, so you can reserve one during the busy season if you are worried about availability.

Again, it’s easy to arrange for a taxi. You can also walk if you’d like (the views are great, 1.5 miles from Great Harbour) or dinghy over to the bay in settled weather. If there are strong trades blowing, you might have a wet ride back though!

Staying in one of these bays gives you additional options for dinner. If in Great Harbour, you can also visit Foxy’s in the evening, another establishment that has gained in popularity similar to Soggy.

white bay east side jost van dyke
View from the east side of White Bay | Notice the nearby cruise ship!

Pick up a mooring ball on the east side of White Bay

If you want to stay close to the action (and White Bay is not redlined by your charter company), there are several moorings on the east side. Pay for it ashore at Ivan’s.

The east side of the bay is always less crowded, and quieter. Plus, it has more room than the west end.

You can dinghy over to the other beach bars, or simply walk along the shore.

Palm Tree that was commemorated for us following a donation to the Hurricane Irma community fund.

I love White Bay and it will always have a special place in our heart with the memories it has created over the years. We will continue to be patrons of White Bay JVD, but our dollars might be dry the next time we visit!

If you want to learn more about the British Virgin Islands or read other articles I’ve written about this destination, check out my British Virgin Islands page.

BVI Weather and Marine Forecast Resources for Sailing

example of backwinding while anchored

During my first bareboat trip to the BVIs many years ago, I didn’t pay much attention to the weather forecast. Big oops!

Everything was fine and we enjoyed the steady 10-15 knot easterly trades and an occasional isolated thunderstorm – typical British Virgin Islands weather. But – what if we were caught in Cane Garden Bay when a northerly ground swell picked up at 2:00am?

It could have been dangerous and at a minimum quite uncomfortable for the crew.

As I’ve become more experienced (and wiser with age) I watch the BVI weather like a hawk before and during our sailing trips. I’ve even figured out how to use an Iridium GO! and download Predict Wind forecast data over satellite.

The good news for the BVIs is that with decent cell phone coverage throughout the sailing grounds, you can get everything you need from the palm of your hand.

In this post, I’ve collected all the info you need to plan for and monitor the BVI weather for your next boat trip. And, given the proximity of the BVI neighbors – USVI and Spanish Virgin Islands – this weather info will be just as good for those sailing destinations as well.

Here’s what I’ll cover:

Ground swells are well forecasted by NOAA

BVI weather features to watch out for

Northerly ground swells

This one can catch novices by surprise. Ground swells can affect northerly exposed anchorages, making them uncomfortable and potentially dangerous.

From Nov-Apr, strong storms in the far away North Atlantic produce these swells that then travel all the way down to the British Virgin Islands.

The result can be extremely rolly anchorages and even breaking waves on the shore. Boats have been known to be thrown ashore from ground swells, so take caution.

The good news is they are extremely well forecasted, so check that forecast often. You can also see the Cane Garden Bay surf report. For a live shot, check out Quito’s webcam.

Notable BVI destinations affected by ground swells:

  • Cane Garden Bay: if any ground swell is forecasted, we avoid CGB. Try Diamond Cay or other Jost Van Dyke anchorages instead

  • The Baths: while not an overnight destination, the mooring field will be quite rolly and swimming ashore from the dingy tie-off can be very dangerous. If you don’t have schedule flexibility and need to fit it in, you have two options

  • Cooper Island: swells can wrap around into the mooring field, again, making this one unpleasant

example of backwinding while anchored
I was backwinded during this lunch stop at Muskmelon Bay | Easterly trade winds, but yacht is facing west

Backwinding while anchored

Backwinding is possible at some popular BVI anchorages. Make sure you understand what it means and how to plan for it. You can see at example above at Muskmelon Bay at Guana Island.

  • Strong winds (~15+ knots) blow, in this case from the easterly trade winds in the BVIs

  • When the wind reaches this speed and blows over tall terrain (like many of the BVI islands), it doesn’t just blow straight over. A vortex is created and creates wind at the surface in the opposite direction of the trades.

  • So despite easterly trade winds, at the surface you may experience a westerly wind which would push your catamaran towards the shore (see the picture above when we were anchored at Muskmelon Bay – the bow is oriented towards the west as a result of being backwinded)

  • Given how close you have to be to shore, it can be a concern at some BVI anchorages due proximity to the shoreline – this can happen at White Bay, for example, when the wind is from the NE

  • Being backwinded can be acceptable if you plan for it and have enough swinging room to manage the phenomenon

Typical day in the British Virgin Islands with puffy trade wind cumulus clouds

What is the weather like in the British Virgin Islands

It’s wonderful!!

But seriously you’ll enjoy some of the best conditions for sailing anywhere.

Generally, for weather conditions, you can expect steady 10-15 knot trade winds from the ENE-ESE, puffy tradewind cumulus clouds, and an occasional shower or squall.

Here’s what you can expect during the various cruising seasons.

High season (December to March)

This is the busiest time of year. Hurricane season is over, and the annual pilgrimage of cruising boats has made it’s way from mainland U.S. and Europe to enjoy the warm Caribbean winter.

Days are shorter (~11 hours vs ~13 hours in the summer).

Most notably, you can expect the Christmas Winds: several days of strong winds (15-30 knots) created by strong high pressure systems in the Atlantic. Make sure you know how to reef those sails!

Wind is usually out of the E to NE and less precipitation falls this time of year.

Shoulder season 1 (April to June)

This is my favorite and I believe the best time to visit the British Virgin Islands for sailing trips. We’ve been to the BVIs 3x in May. The crowds have thinned out somewhat and the weather has become more settled.

Expect easy 10-15 knots from the E to SE and an occasional shower to cool things off.

Peak hurricane season (July to October)

It can be hot, the trade winds lessen (5-15 knots), and tropical mischief can be brewing.

But, you might have the place to yourself. On the flip side, however, some establishments are closed, so keep that in mind if you are planning to hop around the beach bars.

This is the wet season thanks to developing low pressure systems.

Shoulder season 2 (November)

This is my second favorite time to sail in the Caribbean.

Again, the crowds haven’t arrived yet and the weather tends to be settled – similar to April-June.

Trades blow 15-20 knots with wind direction from the E.

The biggest downside of this time of year is the lessening daylight. It can make a difference if you plan to spend long days on the water.

Want to learn more about sailing in the British Virgin Islands? Check out my BVI Beginner’s Guide for other useful insights.