Last Updated on February 12, 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!
Pin this Guide to Virgin Islands Sailing Charters for later!
This article contains affiliate links. If you click through and make a purchase, I might earn a commission, at no additional cost to you. Thanks for your support in this way! Learn more in my Disclosure Policy.
Virgin Islands Sailing Charter Quick Tips
- I’ll share more individual options later in the article, but these links can give you a preview of costs, options, and availability of Virgin Islands sailing charters, including the one we chose:
Airbnb Virgin Islands Charters | VRBO Virgin Islands Charters | Guiding Light Charter
- And if you’re a solo traveler or looking for a hack for sailing the Virgin Islands on a budget, check out small group sailing tours from G Adventures
- 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
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!)
Love the USVI? Be sure to check out my guide to the best Airbnbs in 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 island of St. John is ⅔ undeveloped, including a national park perfect for snorkeling and hiking. Further south, St. Croix offers colonial history and tours of the Cruzan Rum distillery.
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.
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.
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 Holiday-Weather.com.
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.
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.
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.
Guiding Light Catamaran Charter
- Yacht 800 sq. ft.
- Sleeps: 6
- Bedrooms: 3
- Bathrooms: 3
- Min Stay: 5 nights
BVI Catamaran Charter Boat
- Boat
- Sleeps: 8
- Bedrooms: 4
- Bathrooms: 4
- Min Stay: 3–7 nights
Vivo Catamaran Charter: Luxury at an Affordable Price
- Yacht
- Sleeps: 8
- Bedrooms: 5
- Bathrooms: 5
- Min Stay: 5 nights
Sea Witch 58 Foot Luxury Pearson Sailing Yacht
- Yacht
- Sleeps: 4
- Bedrooms: 3
- Bathrooms: 2
- Min Stay: 2 nights
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.
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.
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. 😉
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.
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.
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.
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.
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.
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!
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.
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.
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.
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.
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.
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 ratings and booking:
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.
Snorkeling, Charter & Liveaboard Packing List
Liveaboard boat trips are an amazing way to experience snorkeling and diving destinations, but what should you bring? Grab these tips for what to pack for any snorkeling or diving trip, whether based on land or a liveaboard sailing trip.
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.
Pin this guide to BVI & USVI Sailing or share with a friend!
The Haphazard Traveler is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to Amazon.com. As an Amazon Associate I earn from qualifying purchases.
