The Ultimate Guide to Sailing the British Virgin Islands

January 10, 2025

beach, beach bars, boat, caribbean, cocktails, Destinations, happy hour, islands, pizza, sailing

All I could think during my sailing trip around the British Virgin Islands was “wow.”

Let me set the stage for you.

You wake up on a sailboat, bouyed in the harbor of a Caribbean island. The sun is out, warming your skin all over, but the breeze and passing clouds make the temperature nothing short of ideal. All you can hear for miles is the slightest calm crashing of the waves, and maybe a few seagulls flying. The water is aqua. Not blue, not green, not even turquoise. It is a bright, almost neon, aqua. You see the outlines of coral reefs surrounding the islands, and you can’t wait to get your snorkel mask on. On shore, there is little to nothing except maybe a few beach bars scattered around. Your days are filled with snorkeling, sailing, swimming, paddle boarding, and drinking delicious tropical cocktails all day long. The nights are filled with dinners on the beach, stunning sunsets, and nights at bars that you have to dinghy to because they are nothing but a decked-out pirate ship in the middle of the ocean. This is the life. This is the life I lived for a week in the British Virgin Islands, and I’m telling you all, this place is paradise.

The British Virgin Islands are hard to get to, which is what makes them so stunningly unspoiled. Cruise ships can’t dock in the harbors, so sailboats and private yachts are the only ones who enjoy the islands. I’m almost positive you can’t get anywhere without a boat, so if you’re planning a trip, you’re going to want to look into sailboat rentals. Don’t know how to sail? You can even rent one with a captain and a chef! (THIS is the way to do it, yall!!!) Many of the sailboats are more like yachts. Ours fit 10 people comfortably and had a huge back deck for eating/drinking/playing cards & liars dice. Our boat was a catamaran, which I loved, not only because of the smooth sailing, but because we loved lounging out on the hammock in the front of the boat, too!

When to Sail the British Virgin Islands

The weather is key for the BVIs, so do lots of research. The first time we went in May and it was PERFECT, the second time, we did end of January and it was also ideal! But our friends had gone in the middle of summer and said it was too humid and hot. Alternatively, you can get a house to base from for most of your stay (I’d recommend one of the villas at Scrub Island BVI) , and just take a sailboat out for a day or a few days.

The islands of the BVI

The British Virgin Islands (BVI) are a cluster of over 50 breathtaking islands—with only about 15 of them inhabited! This dreamy sailing destination is home to four main islands: Tortola, Virgin Gorda, Anegada, and Jost Van Dyke. Each has its own unique charm, from Tortola’s bustling energy to Anegada’s secluded, ethereal coral beauty.
Tortola is the largest island, but it’s still only 12 miles long and 3 miles wide, so everything feels intimate and accessible. Virgin Gorda is all about those granite boulders and stunning beaches (hello, The Baths!), while Jost Van Dyke is home to the best beach bars in the world—Soggy Dollar, anyone? And Anegada? A whole different vibe—flat, remote, and home to some of the best lobster you’ll ever eat.
And here’s a fun fact: Sir Richard Branson (you know, the Virgin Group billionaire) owns not one, but TWO private islands here—Necker Island and Mosquito Island. Talk about a baller BVI setup!
Whether you’re sailing between them or soaking up every second on just one, the BVIs are truly paradise on earth.

How to rent a sailboat in the BVI’s

Rent a luxury catamaran – complete with a chef and captain on VRBO! Something like the one we did (fill out this form to learn more!) or this one would be fabulous. You can also reach out to Charter Smarter and specify what you are looking for and they can help match you with a charter (just be sure to let them know Jetset Christina sent you!)

Matching vacation outfits by Kenny Flowers!

THE BEST BRITISH VIRGIN ISLANDS SAILING ITINERARY

Our sailing adventure through the British Virgin Islands was next-level dreamy, and it all started with a pre-charter call where we spilled all the details on our vibe—did we want adventure? Relaxation? The best beach bars? (All of the above, obviously.) Our captain took all that into account and crafted the perfect itinerary, balancing smooth sailing conditions with hitting every must-visit spot on our list. The result? The ideal mix of sun-soaked adventure and laid-back luxury, with plenty of time both on land and at sea. Here’s our day-by-day breakdown and in my opinion the perfect British Virgin Islands sailing itinerary:

Day 1:

We kicked off our adventure by flying into EIS (Tortola, BVI) and spending a couple of dreamy nights at Scrub Island Resort to ease into island time before hopping on board. You totally don’t have to do this—you can head straight to your sailboat—but let’s be real, there’s no such thing as too much BVI time. The turquoise waters and laid-back island vibes had us more than ready to set sail!

Once we boarded, we settled in, unpacked, and immediately dove into our first meal—a delicious grilled mahi-mahi with a Greek couscous salad (fresh, flavorful, and exactly what you want to eat on a boat in the Caribbean). After lunch, we kicked back and soaked up the magic of our first sail—champagne in hand, salty breeze in our hair, and that surreal we’re actually doing this feeling.

By sunset, we arrived at Bitter End Yacht Club for golden-hour cocktails (perfection), before heading back to the boat for dinner—because let’s be real, the best food in the BVI? It’s on your boat. More on that later.

Day 2:

Bitter End Yacht Club

We spent the next day at the iconic Bitter End Yacht Club, a legendary destination for sailors. Fun Fact: This yacht club used to be coat and tie only dress for men!!! But, nowadays, it’s a casual, luxurious beachy hideaway was perfect for a sunset and overnight stay in their harbor. Their food is also great at Bitter End, if you choose to do lunch or dinner on shore. We loved soaking up the beach, hammocks, and crystal-clear waters, shopping at their island boutique (so cute) and ordering a few painkillers (the delish cocktail made famous in the BVI!).

Day 3:

The Baths at Virgin Gorda

Sailing to The Baths at Virgin Gorda was a huge highlight of our sail charter around the British Virgin Islands. We timed our arrival just before sunset (shoutout to our captain for the expert planning), and let me tell you—it was IDEAL. The Baths were practically empty, giving us this rare, serene experience of having the stunning place to ourselves. During the day, The Baths can get super packed, which is not fun when you’re battling hundreds of cruise-ship-crowds, so if you want that postcard-worthy experience, go early in the morning or just before sunset like we did. And pro tip—time your visit for an “open” day so you can actually swim in. It was hands-down one of the most unforgettable moments of the trip!

We arrived just before sunset (thanks to our captain Tim’s guidance) and it was INCREDIBLE- no one was there! During the day the Baths get suuuuper crowded and it’s just not the same experience – so go early in the morning or just before sunset- and time it on a day when it’s “open” which means you can swim in like we did! So so fun! (Also bring a waterproof phone case for pics when you’re there!)

Day 4:

Peter Island

Peter Island was next on our itinerary, and it’s a must-visit for anyone sailing the BVIs looking for a luxe beach day! Access to the pool and beach costs $50 per person, or you can dine at the Drunken Pelican restaurant for free. We opted for a full day enjoying the island’s luxurious beach, pool, floaties, and pickle ball courts!

Day 5:

Norman Island

We anchored outside Willy T’s, the BVI’s legendary floating pirate ship dive bar, and let’s just say—it did not disappoint. This spot is all about the fun, the rum, and the rite of passage that is jumping off the side of the boat (yes, it’s called walking the plank, and yes, you HAVE to do it!). Drinks are strong, the crowd is rowdy, and it’s the perfect place to let loose for a bit before sailing off into another epic day.
The next morning, we stayed put in Norman Island Bay for a full day of watersports, soaking up every second of life on the water. Between paddleboarding, snorkeling, and e-foiling (aka my latest obsession—motorized surfing that makes you feel like you’re flying), we had no shortage of adventure. And when we weren’t out playing? We were kicking back on the catamaran, indulging in the most incredible food from our charter chef, who, let’s be real, could run her own five-star restaurant. It was the perfect mix of thrill and chill, and exactly what a day in the BVIs should be.

Night 5: Cocktails @ Foxy’s Bar

We spent this night like every night in the BVI should be spent – feet in the sand, drink in hand, and live music filling the air at the iconic Foxy’s Bar. This spot is the definition of island vibes, with a festive atmosphere, killer cocktails, and the kind of live music that makes you want to dance barefoot under the stars. We soaked it all in, loving every second of the easygoing, feel-good energy that makes Foxy’s such a must-visit.
After an unforgettable night, we hopped back on board for a delicious steak dinner, a few glasses of wine, and some competitive game time. We brought our favorite game, Liar’s Dice, but the boat had tons of options, which made for the perfect laid-back, laughter-filled night. The next morning, we made our way to the iconic Soggy Dollar Bar at Jost Van Dyke. Spending the day sipping Painkillers and soaking up the sun on this famous beach was the perfect way to end our adventure. Arrive early to snag a prime spot on the beach!

Day 6:

Soggy Dollar Bar

We spent our last full day in absolute BVI paradise—lounging on the white sands of Jost Van Dyke at the iconic Soggy Dollar Bar at Jost Van Dyke with Painkillers in hand and not a care in the world. And let me tell you, our captain nailed it when it came to securing the prime mooring spot, putting us front and center for the ultimate beach day. The whole experience was a dream—turquoise water, incredible energy, and island vibes so good, I’m officially calling it: Jost Van Dyke is my favorite island in the BVIs!. Arrive early to snag a prime spot on the beach

And… the best part? A nearby boat told us there were dolphins about 500M away that afternoon, so we quickly dinghied out to them, snorkels in hand, a couple painkillers deep, and jumped in – we SWAM WITH DOLPHINS!!! It was the most ethereal, most beautiful experience I’ve ever had. They were so angelic – and swimming with them in the wild has been a lifelong dream of mine since I was a little girl. I will never get over the experience. A dream come true.

Soggy Dollar Bar continues its magic of always delivering the BEST days of all time – every single time I’ve been there!

We flew out of St. Thomas the next day but if you can with your flight path it would have been easier to fly out of the British side (EIS, Tortola airport) however they have less flights available.

JETSET TIP: The weather was too windy for us to sail to Anegada, but if you have time on your charter—GO!!!!!! This island is supposed to be the highlight of the British Virgin Islands, and, because it’s the farthest of the BVIs, it feels extra secluded and untouched. Think endless stretches of powder-white sand, crystal-clear waters, and the kind of laid-back energy that makes you want to stay forever. The beaches here? Insane. Loblolly Bay and Cow Wreck Beach are straight out of a screensaver, perfect for kicking back with a rum punch in hand. Oh, and did I mention Anegada has the third-largest coral reef in the world?! If you love snorkeling, this is the place to be—shallow reefs packed with vibrant marine life, just waiting to be explored. And the food? LOBSTER. Anegada is famous for its fresh lobster, so do yourself a favor and indulge in a Caribbean beach lobster feast while you’re there.
Sailing to Anegada is also an experience in itself—since it’s a low-lying coral island, it literally just rises up from the horizon as you approach. A true hidden gem of the BVIs!!!!!

shop our matching outfits here

WHAT’S INCLUDED IN A SAILING CHARTER IN THE BVI

Chartering a sailing yacht in the BVI’s is ALL-INCLUSIVE which is amazing – I can’t recommend it highly enough. We’ve bare-boated once and done a charter with a chef and captain once, so I’ve done it both ways! But most recently, we chartered a sailing yacht with a captain and chef and the experience was soooo luxurious – the charter came with so many things that made the experience seamless and stress-free:

All-Inclusive Meals and Drinks: 5-star meals (3 meals a day!) tailored to your specific preferences and an open bar with premium spirits (that the crew will use to make increeedible cocktails) and wine and beer. Picture yourself sipping on freshly blended strawberry mint margaritas or creamy piña coladas while you take in the island breeze as you sail. Our chef would even set up things like an island rum tasting, sampling the best of the Caribbean. And every morning, you’ll be in heaven with breakfasts complete with deliciioooous breakfasts paired with delicious lattes crafted to perfection using an onboard espresso machine! This is LUXURY, y’all. I was in absolute paradise with the food & drinks on our yacht.

We had things like homemade poke bowls for lunch, and dinners ranged from freshly grilled mahi-mahi and gourmet couscous salads to the most delicious steak and veggies one night, and a shrimp pasta that I will dream about forever! Every meal and drink is an experience, designed to elevate your time sailing.

Watersports Equipment: From snorkeling gear and paddleboards to kayaks, fishing equipment, and an e-foil surfboard (SOOO much fun), everything you need for fun on the water is onboard.

Fully Crewed Charter: The experienced crew will take care of all the sailing, cooking, and cleaning, allowing you to fully relax.

Luxury Amenities: Our yacht featured air-conditioned cabins, spacious common areas, and Wi-Fi so we could stay connected while enjoying paradise.

WHAT TO PACK FOR THE BRITISH VIRGIN ISLANDS:

bikini linked here

JETSET TIP:

Leave some room in your bag! Each stop along the way offers incredible local merchandise, from Soggy Dollar Bar t-shirts to handcrafted jewelry. You’ll definitely want to bring home a few souvenirs to remember your trip.

FAQ about sailing the British Virgin Islands

Did you get seasick?
Not at all, and trust me, I was worried about it! Our captain was an absolute rockstar, keeping things smooth even when the winds picked up. But here’s my go-to tip: avoid staying inside while the boat’s moving—that’s a recipe for queasiness. Instead, head outside, soak up that fresh ocean breeze, and leave your phone behind. I packed non-drowsy Dramamine and ginger drops, which work like magic if you need them (though I didn’t!). The whole experience was smooth sailing—literally.

Will I feel cooped up on a sailboat?
No way! The beauty of a sailing charter is that your itinerary is as flexible as you want it to be. Love land adventures? You can plan your stops to spend lots of time onshore. Plus, the boat is so spacious and comfy, it truly feels like a floating boutique hotel. Every day, we anchored somewhere new, so it never got repetitive. It’s the perfect blend of adventure and relaxation.

Can I book a shorter or longer charter?
Of course! While 7-night charters are the standard, you can absolutely customize your trip to fit your schedule. Whether it’s a quick 4-night getaway or an extended 14-night tropical escape, the experience can be tailored to make sure you get exactly what you’re dreaming of.

What’s not included?
Flights, onshore meals, excursions, and gratuities are not part of the charter rate. Gratuities usually range from 15% to 20% of the charter fee, depending on how much you loved your trip (which will likely be a lot!). But everything else—from gourmet meals onboard to the crew and water toys—is included.

What’s included in the rate?
The all-inclusive rate covers pretty much everything you’d want on the boat: water toys, crew services, cruising permits, taxes, and mouthwatering meals paired with an open bar. No stress, no hidden fees—just a seamless, luxe vacation.

How customizable is my charter?
Completely! This trip is all about you. From the destinations you visit to the meals and drinks served onboard, everything is personalized to your preferences. Fill out a pre-charter questionnaire, and the crew will bring your dream vacation to life. The plan is flexible, so if weather conditions shift or you decide to explore something unexpected, it’s all part of the adventure.

Can I bring my family (kids, babies) on board a sailboat in the BVI?

Absolutely! We did! That said, traveling with toddlers, babies, or children on a boat does come with added responsibility—our son wore a life jacket the whole time, and our baby stayed safely strapped in when we weren’t in a secure indoor space. If your kids can swim, even better! But no matter their age, the crew is there to help make the trip as seamless as possible.

Just be sure to choose a boat that is designed to be family-friendly, making it the perfect choice for a vacation with kids of all ages. You want a captain that is great at catering to families and will go above and beyond to create a magical experience for everyone, so whether you’ve got toddlers or teens, they’ll love it. From kid-approved meals to exciting water activities and even treasure hunts on the beach, your little ones will have the time of their lives. Plus, the spacious layout of the right yacht will ensure everyone has plenty of room to relax, play, and enjoy. We did bring both of our kiddos on board but we had nannies (my parents!!) with us which helped a ton!! The kids also slept SO well on the boat (as did everyone) with the light rocking. It was amazing. I wish I could have it every night – kind of like an adult SNOO, haha.

If you’re looking for a boat that will be family-friendly, reach out to Charter Smarter (let them know I sent you) and inquire about family-friendly sailing charters in particular!

This set up worked well for our family, who are very comfortable traveling with little ones, however, of course, I need to note that traveling with little ones who don’t know how to swim yet on a sailboat carries enormous responsibility and necessary caution – Harrison our son wore a life jacket the whole time on board (this bright orange one which was great) and our baby daughter is not yet mobile, so was always inside in the interior cabin safely or strapped on (such as in her carrier on one of us in the safe interior of the boat or in this high chair, which we were so glad we brought – was awesome to have on board!). We did not feel nervous on board at all (once you realize how spacious and safe you can make it, however, I was nervous leading up to the trip about having them on board! So I can imagine a trip like this being IDEAL in a few years when they can both swim and we can have a little less anxiety around their safety. However, I am SO glad we did it (and SO glad we had my parents with us to help!)

What is the food like on sailing charters with a hired captain and chef?
Unreal. Think restaurant-quality meals every single day! We experienced fresh sourdough avocado toast in the mornings and gourmet dinners like grilled mahi-mahi or shrimp pasta, every meal is seriously a highlight. And the cocktails? Next level—strawberry mint margaritas, island-style piña coladas, and rum tastings that celebrate the Caribbean. Trust me, you’ll be dreaming about the food long after your trip ends.

Where to Go in the BVI :

Breaking it Down by Island

JOST VAN DYKE

My very favorite island of the whole trip. If you’re in the BVI’s,you have to go here. No I mean it. You have to go to Jost Van Dyke. Right now.

white bay

White Bay, as if the pictures don’t do it enough justice, could not be more unreal. Pristine white beaches lined with beach bars, such as the famous Soggy Dollar Bar, make this bay a hotspot for anyone and everyone in the area. We came into White Bay during the day when the whole beach was hopping with boats blasting Jimmy Buffett, people paddleboarding and swimming into shore with beers in hand, and groups of sailors coming in for their mid-afternoon painkillers (a boozy coconut, pineapple, and OJ rum cocktail Soggy Dollar is famous for). This picturesque little slice of heaven was gorgeous, surreal and so much fun.

soggy dollar bar

We spent the entire afternoon at this bar and I can say, without a doubt, that it is the best bar I’ve ever been to. The bar is named the “Soggy Dollar” because there is no way to get there except to swim in, leaving travelers like us with our soggy dollars to pay for drinks. It is such an experience, and the painkillers (their famous drink) are to die for. They also have yummy food and some competitive ring-toss bar game that the guys loved. If you’re in the BVI’s, don’t even think about missing out on the Soggy Dollar. Day drinking followed by an afternoon nap on one of the hammocks that line the beach? It just doesn’t get much better.

foxy’s beach bar

Located in Great Harbor, just down the island from White Bay, Foxy’s is another famous beach bar experience. Whereas Soggy Dollar takes the cake on the daytime scene, Foxy’s is your nighttime go-to. They serve a great dinner, have lots of TV’s for sports, and have DJs or bands playing at night. So much fun!

the bubbly pool

If you’re looking for a day trip on Jost Van Dyke, the bubbly pool and lunch at Foxy’s is a great option. The bubbly pool, kind of like a natural hot tub formed by rocks in the ocean, are really cool but you have to go at the right time when the tide is high, or else it is underwhelming. Around the pool, you can climb up the rocks on the back side of the island and see some great views. After this, grab lunch at Foxy’s Taboo, owned by the same Foxy we met at Foxy’s, this place has some GREAT food and drinks for lunch.

VIRGIN GORDA

Virgin Gorda, one of the largest islands, is full of pristine beaches, luxury resorts, and great sailing. It’s definitely a must-do, and here’s why.

bitter end yacht club

I’m not sure what heaven looks like, but if I had to guess, it would look a little something like the Bitter End Yacht Club.

the baths

This gorgeous area on the southwest coast of the island is unlike any other beaches in the Caribbean. White sand beaches framed by HUGE granite boulders create caves and grottos with amaaaaazing snorkeling and some of the prettiest sights you’ll ever see.