photo of a catamaran sailing in the virgin islands

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Last Updated on September 19, 2021

The idea of sailing in the Virgin Islands might conjure up images of celebrities and private yachts.  But it’s one of the Caribbean’s best secrets that you can sail the Virgin Islands on a catamaran or sailboat from Airbnb and VRBO.  Plus, sailing is the best way to explore the white sand beaches, gorgeous scenery, and snorkeling that make the Virgin Islands famous.  Get advice for choosing a sailing charter, plus hacks for day trippers and solo travelers!

After I did a liveaboard snorkeling trip while traveling solo in Thailand, my family decided they wanted in on the adventure.  But as we considered closer options in the Caribbean, we realized that most were large boats with mixed snorkeling and scuba diving groups.  Soon, though, I hit upon a solution: for about the same per-person cost, we could charter a private catamaran to sail the Virgin Islands.

Experienced sailors can hire a “bare boat” charter, where your group skippers, navigates, and cooks for themselves.  But luckily for those of us that don’t know our leeward from our aft, it’s also possible to charter a boat with a captain and crew.  In this guide I’ll share the easiest way to charter a boat and what to expect, the best sights of the US and British Virgin Islands, and all the tips you need to plan an amazing vacation.

Don’t miss my tips on the best Airbnbs in St. Thomas and Airbnb St. John stays to extend your trip!

🛈The Haphazard Traveler Pro Tip
The U.S. Virgin Islands has reopened to tourists. Learn more here about the entry requirements and prior travel certification required. Additionally, all travelers returning to the United States must show documentation of either a negative test or recovery. Find the CDC requirements here and stay safe, friends!

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Virgin Islands Sailing Charter Quick Tips

  • For USVI or BVI sailing day trips rather than a full vacation, check out these tours with great reviews and online booking:

In this Guide to Sailing the Virgin Islands

Virgin Islands Overview | Booking a Charter | When to Visit | Airbnb Charters | VRBO Charters | BVI Sights | USVI Sights | Getting to the Virgin Islands | Virgin Islands Sailing Packing Tips

Things to Do in the Virgin Islands

Virgin Islands Sailing Overview & Planning

What to Expect Sailing in the Virgin Islands

How does a totally effortless vacation sound, with your only decisions being when to eat, snorkel, lounge, and drink tropical cocktails?  What about falling asleep to the gentle motions of the boat and sound of waves, then waking up with views of blue sky and turquoise waters from the portals?  

If you choose a Virgin Islands charter with a captain and crew, you can completely relax! It’s common for couples to crew boats together and take care of everything.  If you choose a boat with just a captain, you’ll likely pick up some sailing skills helping out.  And members of your group can pitch in to take turns preparing meals and cleaning up.

For those who haven’t spent much time on a boat, the living space might be smaller than you expect. But you’ll have the ocean and beaches for your playground every day, and can arrange the itinerary to go ashore for dinners at low-key beach restaurants.  In short, pack bathing suits, sunscreen, cover-ups, and casual dresses, and leave the heels at home!  (More packing tips later!)

photo of a catamaran sailing in the virgin islands

Love the USVI? Be sure to check out my guide to the best Airbnbs in St. Thomas!

aerial view of St. Thomas

Airbnb St. Thomas Virgin Islands: Budget to Luxury Beach Escapes

Advice on the best Airbnb St. Thomas stays for a tropical escape, from budget condos to mid range resorts & luxury villas for a group. Includes bonus tips on the best beaches, sights, and tours for planning your getaway.

About the Virgin Islands

Did you know there are actually three different groups of Virgin Islands?  Well, I didn’t, until I took this trip!  The British Virgin Islands are the most popular and well-known.  Made up of over 50 islands, the BVI are some of the least-developed spots in the Caribbean, but their largest islands are renowned as luxury destinations.  The beautiful beaches and party bars of Jost Van Dyke are here, as are the picturesque grottoes of the Virgin Gorda Baths.

Just 20 miles away lie the US Virgin Islands, known as “America’s paradise.”  Its three islands – St. Thomas, St. John, and St. Croix – each has a different attraction for travelers.  St. Thomas is famed as a luxury getaway, while the island of St. John is ⅔ undeveloped. Still, there are tons of things to do in St. John, including a national park perfect for snorkeling and hiking.  Further south, St. Croix offers colonial history and tours of the Cruzan Rum distillery in addition to spectacular snorkeling.

The Spanish Virgin Islands are actually part of Puerto Rico, so the name is a holdover from when the island belonged to Spain.  In the SVI, you’ll find the unspoiled beaches of Culebra and a bioluminescent bay in Vieques.  Many travelers here say that these islands remind them of the quieter BVI of years past.  

US residents can travel in the USVI and SVI without a passport, but will need one to enter the BVI.

Buck Island - St. Croix USVI
Buck Island off the coast of St. Croix, USVI

Booking a Virgin Islands Sailing Charter 

In both the BVI and USVI, there are companies that exclusively provide sailing charter rentals.  If you want a bare boat charter, one of these companies is likely the best option, as they can advise on all the options and considerations for your trip.

However, for a crewed boat, I found that the easiest way to arrange a Virgin Islands charter was to use a site like VRBO or Airbnb.   Both offer online reviews, and their bookings follow the same policies as regular vacation rentals on those sites.  You can also message with the host before you book to ask any questions.

I’ll share more recommended options later in this guide. I always recommend always booking through a reputable company, so that you have assistance should you need it.

view of trunk bay in the US virgin islands on St. john
View of Trunk Bay on St. John, USVI

How Long Should You Stay in the Virgin Islands?

Depending on the length of your trip and options from your captain, you might be able to see all of the Virgin Islands.  On our one-week Virgin Islands itinerary, we didn’t have time for the Spanish Islands, but easily saw all of the best sights of the BVI and USVI.

Because you spend most of your time on the boat, in the water, or on a beach, you’ll get a lot of sun on this trip!  One week was enough for me, with my fair skin and tendency to turn into a lobster.  If you plan to stretch your trip to 10 or 14 days, just keep this in mind when you plan your itinerary and pack.  You’ll have more time to spend ashore at stops than we did, which will help.

Be sure to read my snorkeling packing list for tips on reef-safe sunscreen, dry bags, UPF clothing and more gear for your trip.

The Best Time to Visit the U.S. and British Virgin Islands

High season in the Virgin Islands is December through April, when most of us are looking for an escape from cold winter weather!  Hurricane season begins in June and lasts until November.  Luckily, sunshine is plentiful year round, with daytime temperatures in the high 80’s and nighttime temps in the 70’s. 

If you can travel in May – June or November – early December, the shoulder seasons, you’re likely to find more availability and cheaper rates.

We traveled at the end of April and the weather was nearly perfect, except for a storm that caused my mom’s flight to be re-routed through Puerto Rico.  Luckily she made it onto a small puddle jumper (complete with bawking chicken sounds coming from the hold!) and met up with us just a few hours late.  The weather for the rest of the trip was picture-perfect.

Check weather averages for your dates from

aerial view of Devil's Bay beach on Virgin Gorda Island BVI
Aerial view of Devil’s Bay on Virgin Gorda, BVI

Choosing a Boat: Monohull (Sailboat or Sailing Yacht) or Catamaran

When choosing a boat, you’ll have considerations such as the number of people in your group, the layout of the boat, and your own personal preferences.  Some might want the adventure and experience of a “real” sailboat, while others would prefer a steadier trip with more space and luxuries aboard a double-hulled catamaran.   

While I love the romance and classic adventure of a sailboat, I ultimately prefer a catamaran for a multi-day trip.  They offer more room, usually with a living room between the two hulls.  Double hulls also make catamarans more stable, lessening seasickness and making it easier to walk on the deck.  There’s also netting between the hulls at the front of the boat, which creates an amazing place to relax over the water and watch sunsets!

More luxurious boats have ensuite bathrooms for each cabin; in general, the boats accommodate 2-8 guests.  Be sure to check the layouts of your choices before you book.

Sandy Cay - Virgin Islands Sailing

What’s Included in A Virgin Islands Sailing Charter?

The short answer: it depends.  Each charter listing will include all the details, and you can also clarify additional points before you book. Some rates include all costs, which makes it easier to evaluate; these usually have a set base price which increases depending on the number of travelers.  There might be watersports equipment included like snorkels, water noodles, and paddleboards, which helps you pack less.

It’s common that “provisions” aren’t included: these are all the food, drinks, and groceries you’ll need.  Provisioning can be arranged through your booking company or captain, or you can shop for it yourself.  We chose to pay our captain to provision his boat, but stopped at a local shop to pick up some extra rum and preferred liquors!

Additionally, there could be other extras such as fuel, water, national park permit, etc.  Be sure to check the details of each listing and clarify any points so you can compare your options.

aeral view of Sandy Cay and catamarans in the Virgin Islands

USVI and BVI Sailing Charter Easy Bookings

These options below all have good reviews as well as availability calendars and online bookings.  Note that if they begin in the BVI, it’s still possible to visit the USVI, and vice versa depending on what you agree on with the captain or host.  The USVI and BVI are only about 20 miles apart – but keep in mind that you will need to bring a passport to travel between the two countries!

Airbnb Sailing Charters

Check out these sailing charters for the US and British Virgin Islands from Airbnb. If you prefer to search for your own options on Airbnb, specify a boat under the “unique stays” option. But keep an eye out for bookings that are only lodging: some boats remain at the dock or don’t include sailing.

VRBO Charters

VRBO is another top vacation rental site, and has many options to book sailing charters in the BVI and USVI. Check some of their best-rated charters including the one my family and I booked, the Guiding Light.

photo of a catamaran in the water with a woman

Guiding Light Catamaran Charter

  • Yacht 800 sq. ft.
  • Sleeps: 6
  • Bedrooms: 3
  • Bathrooms: 3
  • Min Stay: 5 nights

photo of a catamaran in the ocean

BVI Catamaran Charter Boat

  • Boat
  • Sleeps: 8
  • Bedrooms: 4
  • Bathrooms: 4
  • Min Stay: 3–7 nights

photo og a catamaran and crew in turquoise waters in the virgin islands

Vivo Catamaran Charter: Luxury at an Affordable Price

  • Yacht
  • Sleeps: 8
  • Bedrooms: 5
  • Bathrooms: 5
  • Min Stay: 5 nights

photo of a sailing yacht in the Virgin Islands

Sea Witch 58 Foot Luxury Pearson Sailing Yacht

  • Yacht
  • Sleeps: 4
  • Bedrooms: 3
  • Bathrooms: 2
  • Min Stay: 2 nights

photo of a catamaran in the turquoise waters of the Virgin islands

Crewed All-Inclusive Luxury 5 Star Catamaran

  • Yacht: 1080 sq. ft.
  • Sleeps: 6
  • Bedrooms: 3
  • Bathrooms: 3
  • Min Stay: 5 nights

Best Sights for Virgin Islands Sailing

Wondering what the top sights are in the BVI and USVI?  Check out these ideas for your Virgin Islands sailing itinerary.

BVI Top Sights | Sights for Sailing in the British Virgin Islands 

The Baths on Virgin Gorda Island

The huge, smooth grey boulders and clear turquoise waters of The Baths are one of the most-recognizable sights of the BVI.  This national park is a must-see spot for Virgin Islands sailing.  Swim in from the bay to snorkel and explore the grotto and calm pools. You can hike from the top of The Baths to the picturesque Devil’s Bay, at Virgin Gorda’s southwestern end.

photo of the boulders on the beach of Virgin Gorda Island

Jost Van Dyke

The smallest of the four main islands of the BVI, Jost van Dyke is rumored to have been named for a Dutch pirate that used the island’s harbours as a hideout.  The island is accessible by ferry service and private boats, as well as cruises that dock and shuttle passengers ashore.  White Bay is a gorgeous white sand beach with many bars like the Soggy Dollar, home of the famous Painkiller cocktail.  On the east side of the island, visit the Bubbly Pool, a natural jacuzzi formed by waves rushing over the rocky shore.  At the Great Harbor, have dinner and drinks at Corsairs restaurant and popular Foxy’s bar.  Nearby, hike and snorkel at Sandy Cay, a tropical deserted island surrounded by a barrier reef.

aerial view of White Bay beach on Jost Van Dyke

Soper’s Hole, West End, Tortola BVI

Soper’s Hole in Tortola’s West End is one of the places where you can clear customs and immigration from the USVI to the BVI.  It has a colorful marina with restaurants and shops which are a good spot for souvenirs.  If you need provisions, stop in at Harbour Market.  Be sure to check out Pusser’s Landing, a bar and restaurant which also claims to be the birthplace of the Painkiller! You should definitely try both to see if you prefer theirs or the Soggy Dollar’s. 😉

photo of the waterfront at Sopers Hole marine

Cane Garden Bay, Tortola

Cane Garden bay is the most popular beach on Tortola, with calm turquoise waters and a beautiful crescent beach.  Swimming, windsurfing and other water sports are popular here, as well as the lively bars and restaurants that line the beach.  Tour the nearby Callwood Rum Distillery, where they’re producing rum the same way they did 200 years ago.

photo of beach and turquoise waters at Cane Garden Bay Tortola

Norman Island & The Indians

Norman Island is a BVI gem rumored to have inspired the Robert Louis Stevenson classic “Treasure Island.” Snorkel right into the high cliff face at the island’s famous caves which are full of marine life.   Nearby, you can also snorkel on the Indians, a dramatic series of rocks as you approach Norman Island.  The water on one side of the Indians is deep, but the reef is full of colorful coral, sea fans, and marine life.  The Indians are a must-see spot for BVI sailing.  At Norman Island’s protected anchorage area known as “the Bight,” visit local bars and restaurants including the floating bar Willy T’s and Pirates Bight restaurant.

underwater photo of a coral formation

RMS Rhone

The RMS Rhone is a shipwreck that sank in 1867 during a category 3 hurricane.  Now, the wreck site and surrounding waters are the Rhone National Marine Marine Park.  This is an amazing site for scuba diving, but it’s possible to snorkel as well since the water is very clear.  Much of the vessel is still intact.

Top USVI Sights | Sights for Sailing in the US Virgin Islands

Virgin Islands National Park, St. John

Virgin Islands National Park occupies ⅔ of the island of St. John. Many of the beaches are fringed by coral reefs. They include Trunk Bay, with an underwater snorkeling trail including guide signs with information on the coral and sealife.  The beach here has been voted one of the most beautiful in the world!  Annaberg Plantation has the ruins of an 18th-century sugar plantation, which visitors can tour to learn more about the plantation’s role in the African slave trade as well as how it produced sugar, molasses, and rum. Trails through tropical forests lead to the ruins of Reef Bay Sugar Mill, in the south.

photo of a bay and mountains of the national park in the US Virgin Islands on St. John

Cinnamon Bay Beach, St. John

Cinnamon Bay Beach is one of the most beautiful and pristine beaches within the National Park. It’s the longest beach on St. John, with a half mile of white sand plus palm trees and sea grapes for shade.  Snorkelers can explore the small cay located less than 100 yards off the shoreline. This beach is still recovering from Hurricane Irma, and doesn’t have any restaurants.

photo of pristine beach in the USVI - Cinnamon Bay

Buck Island, off St. Croix

Off the coast of St. Croix lies uninhabited Buck Island, 175 acres of protected land surrounded by 19,000 acres of the Buck Island Reef National Monument. The barrier reef is a nesting area for three species of sea turtles, and also has an underwater trail through coral and sea fans.

Caribbean Gem: Buck Island Reef National Monument (Short Film, 2014)

Leinster Bay & Waterlemon Cay, St. John

Waterlemon Cay is tiny island in Leinster Bay, and a top snorkeling spot on St. John with many species of coral, fish, and marine life.  A strong current sometimes runs on the north side of the cay, so use caution snorkeling there.  On the south side, find longspine sea urchins, many fish, and hard and soft corals.  This was another of my favorite snorkeling spots on our trip!

aerial view of a small island in Leinster Bay

Salt Pond Bay, St. John

Salt Pond Bay has a beautiful crescent shaped beach with calm, clear waters.  This is a more secluded beach, as it’s further from tourist spots, and also a quarter mile hike from its parking lot.  Salt Pond Bay is one of the top snorkeling locations on St. John, and has access to hiking trails that provide views of the island. 

Salt Pond Bay hike - St. John USVI

Maho Bay, St. John

Maho Bay is a popular spot to see sea turtles. The seagrass beds in the middle of the shallow bay provide a habitat for the green sea turtles.  There are also reefs at the eastern and western ends of the shore with hard and soft corals and many tropical fish species.

Maho Bay St. John USVI

Sandy Point, St. Croix

Sandy Point is a pristine beach on the southwestern tip of St. Croix that is also a national wildlife refuge.  If it looks familiar, it was featured in the movie “The Shawshank Redemption.”   The 400-acre reserve is a habitat for leatherback sea turtles.  Since it’s a wildlife reserve, there are no beach bars or services here – just uninhabited beaches.

Sandy Point - US Virgin Islands St. Croix

Magens Bay, St. Thomas

Beautiful Magens Bay is one of the most popular beaches in the USVI, with a mile-long stretch of sand with calm clear waters.  It’s known as a spot for snorkeling with sea turtles as well as paddleboarding and other water sports.  Relax at the beach bar and restaurant  for a drink and a snack.

Magens Bay - St. Thomas USVI

Getting to the Virgin Islands for a Sailing Charter

US Virgin Islands Airports, Ferries and Taxis

There are two major airports in the Virgin Islands: Cyril E. King Airport on St. Thomas (STT) and Henry E. Rohlsen Airport on St. Croix (STX).  Most charters start from St. Thomas.  

Check flights to St. Thomas STT | Check flights to St. Croix STX

There is a ferry that runs from St. Thomas and St. John between Red Hook and Cruz Bay.

At the airport, exit to find a taxi stand outside.  Taxis are priced per person based on your destination.  Many run like a shuttle, in a large van with other travelers.  Get an idea of rates and destinations here.

If you’d like to pre-book a private transfer, here are some options with online bookings and good reviews:

British Virgin Islands Airports & Transportation

There are two ways to get to the British Virgin Islands. The first is to fly directly to Terrance B. Lettsome International Airport on Tortola (EIS), formerly Beef Island Airport. The second way is to fly to Cyril E. King airport in St Thomas in the US Virgin Islands (STT) and then take a ferry to Tortola, BVI.  Most charters in the BVI depart from Tortola.

Inter-Island Ferries

There are many ferry services within the Virgin Islands

What to Pack for Your Virgin Islands Sailing Charter Vacation

As I mentioned before, a sailing vacation is very casual!  I recommend packing at least 2 bathing suits as well as a rashguard shirt with UPF (Ultraviolet Protection Factor) to protect you from the sun.  If you’re an avid snorkeler, you might even want UPF capris so that your backside doesn’t get burnt (true story). A dry-bag is a must-have for trips ashore.

Also, there won’t be much room onboard, so be sure to bring a soft-sided bag rather than a regular suitcase.  Get my full packing list for snorkeling trips and liveaboard adventures and check out my list of favorite gear.

More Recommended Gear for Your Trip

Safety Note: USCG Approved Life Jackets for Kids

Your charter will surely provide life jackets for all passengers, but it’s especially important for children to have a life jacket (or personal flotation device – PFD) that is meant for their age, size and weight and approved by the US Coast Guard (USGC).  USGC ratings specify that jackets for infants and small children should have a padded head support, grab handle, and crotch strap to keep it from riding up (and the child from slipping out). 

Get more info here and tips from REI including getting kids used to jackets ahead of time at home.  Note: water wings, float suits, and similar items are meant for supervised play.  US law requires that children under 13 years of age must wear their lifejacket, unless below deck.

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Adrienne, The Haphazard Traveler

I used to be a hot travel mess, but I got better! I kept the name and now blog my best tips for culture and adventure travel from around the globe. Follow along for travel advice, destination info, and photography from faraway lands - and at home in Washington, D.C.

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