Matt and Britney Weidert

Matt Weidert

Sailing the Virgin Islands: What We’ve Learned

When you think about sailing the Virgin Islands, the British Virgin Islands certainly come to mind, and perhaps the US Virgin Islands. But did you know about the third part of the VIs, the Spanish Virgin Islands?

We've sailed in all three, multiple times, and it's our favorite place to charter.

If you're planning to sail the Virgin Islands, find out what I've learned about cruising conditions, when to visit, and what to expect at each of the three very unique sisters of the Virgin Islands.
  • Cruising conditions in the Virgin Islands
    • Virgin Islands weather features
  • Best time to go sailing in the Virgin Islands
  • Three sisters of the Virgin Islands
    • British Virgin Islands
    • US Virgin Islands
    • Spanish Virgin Islands
A typical day in the British Virgin Islands with puffy tradewind cumulus clouds

Cruising Conditions in the Virgin Islands

You’ll enjoy some of the best yacht charter sailing conditions anywhere thanks to the steady easterly tradewinds and the protection in the lee of the islands from waves and swells.

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.

In the winter months, you can expect Christmas Winds to blow occasionally: several days of strong winds (15-30 knots) created by high pressure systems in the Atlantic. This is also considered the dry season.

On the other hand, the summer months are wetter due to passing tropical waves or disturbances. In between, winds tend to be lighter.

Virgin Islands weather features

Navigation is mostly line of sight with the exception of certain areas, such as Anegada. There are few navigational hazards compared to a destination such as the Bahamas.

Tides are not significant, and you can expect a 0.5 to 1.0 knot current that moves from east to west.

Northerly ground swells can catch novices off guard. They affect northerly exposed anchorages, making them uncomfortable and potentially dangerous from mainly Nov - Apr. You can read more about them in this post about BVI weather resources.

Backwinding is possible at some Virgin Islands anchorages if strong winds are blowing (15+ knots) over steep, tall terrain.
Perfect day at Culebrita in the Spanish Virgin Islands

Best time to go Sailing in the Virgin Islands

If you’re planning to go sailing in the Virgin Islands, you should consider the four different sailing seasons:
  • High season: December to March
  • Shoulder season one: April to June
  • Peak hurricane season: July to October
  • Should season two: November
Personally, my favorite time to visit is during shoulder season one. We enjoy predictable weather, longer days, steady wind speeds, fewer crowds, and cheaper charter prices.
Expect crowded mooring fields in the BVI during high season

High season: December to March

This is the busiest and most expensive time of the year in the British Virgin Islands and US Virgin Islands. The Spanish Virgin Islands are always going to be a bit sleepier. 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.

Expect crowded mooring fields, shorter days (almost 2 hours shorter than the summer), and a visit from the Christmas Winds.

Shoulder season 1: April to June

This is my favorite and I believe the best time to visit the Virgin Islands for sailing trips. We’ve been to the VIs 4x 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.
Playa Flamenco in the Spanish Virgin Islands during a passing tropical wave

Peak hurricane season: July to October

Many charter companies put their boats on the hard for hurricane season, but it's still possible to book. Expect great deals, and you might have the whole anchorage to yourself.

Just keep an eye on the tropics - try these strategies for chartering during hurricane season.

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. Some tropical mischief is still possible, but you'll see lower prices than December.
Setting Point in Anegada on our 2023 trip

The three sisters of the Virgin Islands

British Virgin Islands

The British Virgin Islands is the global yacht charter capital, for good reason.

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

I’ve spoken with some old salts that have made over 30 trips!
It’s popularity owes itself to the unique geography, with many islands and bays to explore, sheltered from the trade wind driven swells.

What makes it so great?
  • 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 – the BVIs have few major navigational hazards (if you pay attention to red-lined areas) and the sailing is usually line of sight
  • Amenities – there are bars and restaurants to fill your heart’s desire
  • Mooring balls – plenty of well maintained balls are available, making it easier and less stressful for crews
  • Well established bareboat yacht charter industry – lots of operators, a deep bareboat charter fleet, and many services to help make your trip easy
Beautiful evening in North Sound on our first ever charter

Highlights of sailing the British Virgin Islands
  • Hike through the gigantic granite boulders at the Baths to Devils Bay
  • Anchor in North Sound and enjoy the sights of one of the finest harbors in the Caribbean
  • Sail offshore to the sunken island, Anegada. Sip cold beverages at rustic beach bars on the beautiful north shore
  • Go Beach Bar hopping for painkillers at famous White Bay, Jost van Dyke
  • Jump into the water from the second deck of the floating pirate ship bar, Willy-T
  • Discover abundant marine life at the many snorkeling sites, such as the Indians and the Treasure Island Caves
Magens Bay in St. Thomas is spectacular

US Virgin Islands

The US Virgin Islands don’t get as much attention as their more popular sister next door, the BVIs, but they should for charter crews.

I visited the BVIs four times before exploring a USVI yacht charter. Verdict? I was especially blown away by the Virgin Islands National Park and the beauty of some of the bays.

And, don’t tell the British Virgin Islands, but I think the USVIs have better beaches! (yes I love Anegada’s north shore, but these USVI beaches are more numerous and can be accessed right from your dinghy)

Why might you like a USVI yacht charter?
  • Idyllic Caribbean surroundings – Plenty of protected anchorages. Coconut palm lined white sandy beaches. Great snorkeling and fishing. 
  • 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 some hazards to avoid, but most of the sailing and navigating is point and shoot, line of sight passages
  • Amenities – there are some really fun beach bars and restaurants to visit. There are even vendors you can visit in the National Park
  • Mooring balls – plenty of well maintained balls are available from the National Park Service, making it easier and less stressful for crews
  • Easy logistics – no need for a transfer with many direct flights available from mainland US. You can be on your charter yacht within 30 minutes of landing, seriously!
  • Good for kids -when I take my little kids on a yacht charter for the first time, I think the US Virgin Islands will be the destination. Why? Short passages, plenty of activities, protected swimming/snorkeling areas, and lots of beaches to relax on.
You can't miss the amazing beaches of the Virgin Islands National Park - this one at Maho Bay

Highlights of a US Virgin Islands yacht charter
  • Beach, snorkel, repeat. The Virgin Islands National Park has countless opportunities for snorkeling and beaching all day long. The setting doesn’t get any better thanks to its protected status.
    • Hawksnest Bay for turtle sightings
    • Trunk Bay for the underwater snorkel trail
    • Cinnamon Bay for swimming and gazing at luxurious villas
    • Maho Bay for the awesome beach
    • Leinster Bay / Watermelon Cay for the best snorkeling in the Virgin Islands
  • Cruz Bay and Coral Bay on St. John are fun, quirky towns with lots of shopping, dining, and drinking
  • The south drop is just an hour away where you have great chances of catching mahi, wahoo, and tuna to cook up right on your yacht
  • Marvel at Magens Bay, one of the most spectacular settings I’ve visited in the Virgin Islands
  • Lime away the afternoon and enjoy an epic unobstructed sunset at Honeymoon Beach, Water Island
  • Grab a pizza from the floating pizza boat, Pizza PI VI, at Christmas Cove
You'll often find solitude in the Spanish Virgin Islands - this was on our 2022 guys fishing trip

Spanish Virgin Islands

If you haven’t yet sailed the Spanish Virgin Islands on a yacht charter, you are missing out!

Even though the islands are a couple hours sail from St. Thomas, they still feel largely undiscovered. 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!

You’ll see evidence on your trip of how the US Navy and Marines used these islands for training: target practice tanks on Flamenco Beach and bays that are off limits to anchoring due to potential unexploded ordnance. This is one of the primary reasons tourism here lags its Virgin Islands’ neighbors to the east.

The Spanish Virgin Islands are actually part of Puerto Rico, and it’s easy to coordinate a yacht charter from either the US Virgin Islands or the Puerto Rico mainland. I’ve chartered from both, and I actually prefer from the US Virgin Islands since there is a deeper charter fleet.

The cruising grounds consist primarily of the islands of Culebra and Vieques with several other small islands/cayos mixed in for exploration. If you don’t have a full week to explore, I would spend more time on Culebra.

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. 

Don’t expect beach bars at every anchorage. This is a place to get away from it all and soak in the natural surroundings.
Green Beach, Vieques with a sunset over Puerto Rico in 2020

Highlights of sailing the Spanish Virgin Islands
  • Anchor at picture perfect Tortuga Beach and hike to the lighthouse atop Culebrita for commanding views of the surrounding islands
  • Drop the hook or hike to Flamenco Beach, a global top 10 ranked beach; enjoy $2 Medalla beers from the kiosk vendors and take your picture with the rusting tanks
  • Snorkel the gorgeous reefs on the west side of Culebra right from your yacht, such as at Carlos Rosario
  • Troll fishing lines on the southern drop at Vieques and catch tuna, wahoo, and mahi
  • Book a kayak tour to experience the bioluminescence of Mosquito Bay
  • Experience epic sunsets over the Puerto Rico mainland at Green Beach
  • Take in the local party scene at Isla Palominos on your last night
Hope that was helpful to learn about sailing the Virgin Islands. Check out my Bareboat Charter Guide if it's your first visit to the British Virgin Islands.


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