We’ve been fortunate to travel around the globe to amazing places near and far, but if you ask David where his absolute happy place is, his answer will come without hesitation: the British Virgin Islands (BVIs). For us, the BVIs are truly like an adult amusement park, best enjoyed with a fantastic group of close friends and loved ones. It’s a magical combination of numerous islands, almost all within sight of each other (except for one special exception!), each offering its own unique highlights and reasons to drop anchor and explore. We’ve been fortunate enough to visit these turquoise waters three times, and honestly, we can’t wait to go back!

While there are certainly a number of amazing resorts sprinkled throughout these idyllic islands, we firmly believe the quintessential BVI experience comes from hopping around and embracing the freedom of the open water. And the absolute best way to do that, in our humble opinion, is by chartering your very own 3 or 4-cabin catamaran.

The Call of the Ocean: Our Self-Captaining Journey

The ability to self-captain a catamaran in the BVIs wasn’t just a passing thought for David; it actually became a significant life goal back in 2017. He was utterly captivated by the idea of being at the helm, navigating those stunning waters. It wasn’t a small undertaking – he diligently took multiple sailing courses and tackled rigorous certification exams over the course of two years to make that dream a reality. And let us tell you, there’s an amazing, almost indescribable feeling that comes with having the awesome power of a 50-foot sailboat at your direction, gliding silently across the Caribbean Sea.

However, right off the bat, we want to make it clear that you absolutely do not need to be a seasoned sailor like David to have this exact same incredible experience. Not at all! You can very easily hire a professional captain to be at your disposal, taking care of all the navigation, docking, and general boat handling. And if you truly want to lean into pure relaxation and indulgence, you can even add a private chef to your crew, who will whip up gourmet meals right on board. This makes the entire journey utterly seamless for you, allowing you to focus solely on enjoying the sun, sea, and company.

We’ve found that a 7-night trip is the perfect amount of time to get around to all the major spots and really soak in the BVI vibe, while still leaving plenty for repeat visits – because trust us, you’ll want to come back! When it comes to choosing a yacht charter company, we wholeheartedly recommend Moorings. They are undeniably the biggest player in the game, which means they have plenty of availability and a wide array of boat options to suit different group sizes and preferences. We've personally loved their boats for so many reasons. For instance, we adore the thoughtful design detail of the door in the galley that leads directly to the bow of the boat. This makes it incredibly easy and quick to get to the front of the boat, transforming that forward space into a much more usable and delightful area for lounging or enjoying the breeze. Another fantastic feature we appreciate is the seating area located above the galley. This elevated spot is absolutely perfect for gathering your whole group for pre-dinner cocktails as the sun sets, offering spectacular panoramic views. And if you happen to be chartering a three-cabin boat with three couples, you'll be thrilled to know that one of the cabins takes up an entire hull. This creates an amazing, incredibly spacious retreat that feels larger and more private than many hotel rooms, offering a truly luxurious experience on the water. They put a tremendous amount of thought into the details of their vessels, making it really easy to live on their boats for a week.

When to Go: Our Insider Tips for Your BVI Adventure

Before we dive into the itinerary, let’s talk about timing. The weather in the BVIs is generally fantastic year-round, offering warm temperatures and sun-drenched days. The main consideration is hurricane season, which typically runs from July through October. We’ve found it’s best to avoid this period if possible.

In terms of pricing, the cost for chartering boats changes based on the time of year. The most expensive periods are usually over the holidays (think Christmas and New Year's) and then from February through April, when demand is highest. If you're looking for better value and fewer crowds, we highly recommend the shoulder seasons. November to mid-December and May/June tend to be the cheapest times to visit. We've personally always gone in November, and we've found it to be absolutely lovely. The weather is still fantastic, the water temperature is perfect for swimming and snorkeling, and there are noticeably fewer crowds, allowing for a more relaxed and intimate experience.

Our Dream 7-Day BVI Catamaran Itinerary: An Adult Amusement Park Awaits!

This itinerary is designed to give you a fantastic blend of iconic BVI experiences, hidden gems, and plenty of time for relaxation and fun. We typically recommend going counter-clockwise around Tortola for better winds at most times of the year, maximizing your sailing enjoyment.

Day 1: Arriving in Tortola – The Gateway to Paradise

Your BVI adventure begins with your arrival in Tortola. You have a couple of options here: you can either fly directly into Terrance B. Lettsome International Airport (EIS), also known as Beef Island Airport, on Tortola itself, or you can fly into St. Thomas (STT) in the USVI and then take a scenic water taxi or private boat transfer over to Tortola.

No matter how you arrive, you'll need to spend one night in Tortola before departing the next morning on your boat. On our first trip, we stayed at Maria’s by the Sea in Road Town, and it was perfectly lovely for the pre-cruise night. However, we’ve discovered a much-preferred strategy for subsequent trips: doing a “sleepaboard” on your catamaran. This means you get to "check in" to your boat the night before your official departure and sleep on it right there in the marina. This is an absolute game-changer! You avoid the hassle of packing and unpacking an extra time, and it gives you a fantastic opportunity to get comfortable with the boat's layout, start stocking it with all your favorite drinks and snacks, and just generally settle in before the happy commotion of the next morning when you're trying to get off the dock and underway.

For that first evening, we highly recommend having a nice dinner somewhere on Tortola. Most restaurants are an easy 30-minute taxi ride away at most, and the marina staff are always happy to call a car for you. Some of our favorite spots for that first taste of island dining include: Peg Legs (a casual, lively spot right on the beach), Myett's (often featuring great live music for a fun atmosphere), or the more upscale Brandywine Estate Restaurant (offering exquisite dining with stunning views).

Day 2: Sail Away – Your BVI Adventure Truly Begins!

The morning of Day 2 will be filled with energy and anticipation as you get ready to set sail. There will be some essential paperwork, a boat inspection to ensure everything is ship shape, and you'll get to know your Moorings captain (if you've hired one!) and discuss your desired itinerary for the week. Remember, this is your trip, and the itinerary can always be changed on the fly based on your mood, the weather, or a new recommendation you pick up along the way!

Then, it’s truly time to depart the dock and leave all your worries behind. As you raise the sails and feel the gentle push of the wind across the Sir Francis Drake Channel, it’s full-on relaxation mode. Your first destination will be a small cluster of dramatic rocks known as The Indians. This is a perfect spot for your first lunch on board and an exhilarating snorkel. The underwater world here is vibrant and teeming with life.

After enjoying The Indians, you'll sail a short distance to Norman Island, the legendary inspiration for Robert Louis Stevenson’s Treasure Island. Your anchorage for the first night will be The Bight, a very calm and protected bay. It's a fantastic spot, home to the infamous Willy T pirate ship (a floating bar and restaurant – a true BVI institution!). We always enjoy a visit to the Willy T for a cocktail or three and don’t forget to jump off the second deck of the ship! For dinner, Pirates Bight on Norman Island offers a delicious meal in a beautiful setting. If you’re feeling adventurous before dinner, there’s a great hike that starts just behind the restaurant. It takes you to the opposite side of the island, culminating in a serene, totally private beach – a little reward for your efforts!

Day 3: Exploring Hidden Coves and Sunken Treasures

We suggest continuing your counter-clockwise journey this morning, enjoying those favorable winds! Your first stop is just a stone's throw away: the Caves on the other side of The Bight. This is a perfect spot for a quick snorkel, and who knows, you might even spot some "treasure" – perhaps a glimmering fish or a unique shell!

Next up is a poignant and fascinating stop at the site of the RMS Rhone, a Royal Mail Steamship that sank in 1867 during a hurricane. Best explored scuba diving, we were amazed how much of the wreck you could see while snorkeling. It’s a great place for lunch on the boat after your underwater exploration.

Your final destination for Day 3 is Cooper Island and the charming Cooper Island Beach Club. This is a popular spot for a reason, offering more excellent snorkeling right off the boat or at nearby coves. The Beach Club itself is a lovely spot to go ashore for a sundowner cocktail, perhaps even enjoy their renowned rum bar, and settle in for a relaxed dinner.

Day 4: Natural Wonders and Billionaire's Backyards – Virgin Gorda

Get ready for one of the most iconic and visually stunning stops in the BVIs: The Baths on Virgin Gorda. This unique geological formation features colossal granite boulders scattered across the beach, forming picturesque grottoes, tidal pools, and hidden caves that you can explore. It’s truly like nature’s own playground. Spend the morning climbing, wading, and discovering these incredible formations, and then enjoy lunch back on board your yacht.

As you sail north from The Baths, make sure to get out your binoculars and check out Mosquito Island as you pass by. This is one of Richard Branson’s private islands, and notably, this particular one is available to rent – if your budget allows for an absolutely exclusive escape!

Your journey continues up into the majestic North Sound of Virgin Gorda. We recommend mooring near Saba Rock and the Bitter End Yacht Club. Both are legendary spots in the BVIs for drinks and dinner, offering a lively yet sophisticated atmosphere. We recommend visiting both, one for drinks and the other for dinner.

Upon your arrival in the North Sound, keep a keen eye out for a small boat with a man and his dog, both wearing bright orange. That, dear friends, is Jim and Drake – the famous Rum Runners! They’ll motor right up to your boat and bring you their delicious, potent Rum Runner cocktails.

Day 5: Cruising West and Finding the Best Snorkel Spot (In Our Opinion!)

As you reluctantly leave the North Sound behind on Day 5, wave goodbye to Branson's Necker Island as you start your journey west. You might be tempted by a detour to Anegada (more on that later!), but for now, we're sticking to the classic circuit.

Your next stop is the serene Dog Islands, a lovely spot for a quiet lunch and some excellent snorkeling. Afterwards, you'll moor off of Marina Cay, a tiny, picturesque island with a charming beach bar and restaurant. Dinner here or a short dinghy ride to Scrub Island Resort offers great options.

Now, for a true insider tip and one of our absolute favorite snorkeling spots in the entire BVIs: West End Bay off of Great Camanoe. The clarity of the water and the abundance of marine life here are simply unparalleled in our opinion. Make sure to make time for this underwater paradise. If you find yourself running low on provisions, you can go ashore at Trellis Bay, which is conveniently right near the airport, so if a member of your crew needs to be thrown overboard this is the place to do it!!

Day 6 & 7: The Joys of Jost Van Dyke – Our Top Pick for an Extended Stay

As you continue your westward journey, your next stop should definitely be Monkey Point on Guana Island for a great beach and snorkel combo. Just a friendly warning from us: don’t venture too far past the beach, as there’s a private resort there that isn’t exactly welcoming to charterers.

From Guana, it’s a relatively short and often exhilarating sail to Jost Van Dyke. We absolutely recommend spending two nights here because this island offers three distinct, equally amazing choices for your anchorage and exploration: Little Jost Van Dyke, Great Harbour, or White Bay. Each has its own incredible personality.

Little Jost Van Dyke: This is perfect for a more secluded feel. From here, you can take a short hike to the Bubbly Pool, a natural phenomenon where waves crash through rock formations to create a natural jacuzzi – it's a blast! You can also take a short cruise over to Sandy Spit, a tiny, uninhabited island with a single palm tree, straight out of a postcard – perfect for photos and a quick dip. For dining, Foxy’s Taboo or the B-Line Beach Bar are great choices, with the latter sometimes hosting fun BBQs right on the beach.
Great Harbour: This is where the energy picks up a notch. On your way, be sure to stop at Sandy Cay, another picture-perfect uninhabited island. In the morning, keep an eye out for a woman and her son who come around in a boat selling delicious empanadas from their Sugar and Spice Snack Bar – we always look forward to this treat! Great Harbour is also home to the legendary Foxy’s, famous for its nightlife, especially during its monthly Full Moon Parties, which are epic. There are plenty of casual restaurants like Corsairs and Tipsy Shark. You could also easily take a taxi from here over to White Bay if you wanted to experience both.

Katie and David at Soggy Dollar with Painkillers in hand

White Bay: This is perhaps the most famous anchorage on JVD, and for good reason. We love to spoil ourselves with massages right on the boat in the harbor. White Bay is also home to the world-famous Soggy Dollar Bar, the birthplace of the Painkiller cocktail. The ritual? You literally swim ashore (hence the "soggy dollar" you'll use to pay!). Follow that up with dinner at Hendo’s Hideout, and you've had a truly classic BVI day.

Day 8: Winding Down the Dream

As your final full day in paradise dawns, take a leisurely sail around the western end of Tortola. If you wish, pop into Soper’s Hole for lunch. This charming, colorful marina offers a few great spots to grab a bite and do some last-minute souvenir shopping.

For your last night, we recommend making your way to Peter Island. It’s a convenient location that makes your disembarkation morning much easier. The newly opened Peter Island Resort & Spa offers a fantastic option for a farewell dinner ashore if you're looking for one last indulgence. Alternatively, and often our preference for the final night, simply have dinner on the boat, enjoying your remaining provisions and savoring the last quiet evening under the stars.

Day 9: Departure

On your final morning, it's just a quick, bittersweet sail back across the channel to Road Town, Tortola, where you'll disembark your boat. From there, it’s an easy transfer to Beef Island Airport or the ferry terminal to head home, already dreaming of your next BVI adventure!

Itinerary Options: Customizing Your BVI Paradise Experience

The beauty of a catamaran charter is the flexibility it offers. While we've outlined our favorite classic 7-day circuit, here are some fantastic itinerary options we highly recommend if you have more time or want to tailor your trip even further:

The view from Hog Heaven on Virgin Gorda

Spend an extra night in the North Sound on Virgin Gorda. The North Sound is so captivating that it’s easy to want to stay longer. If you have an extra night here, we suggest mooring near Biras Creek Resort or Leverick Bay. From there, you can catch a taxi up to the fantastic, casual BBQ dive place (in the best possible way!) called Hog Heaven. The name fits, as it boasts some of the best views around – perfect for a sunset meal.

Venture to Anegada Island: Anegada is a truly special BVI island, located significantly north (and out of eyesight!) of the North Sound on Virgin Gorda. It’s a beautiful sail to get there, taking a few hours, but it’s absolutely worth the journey. Anegada is strikingly different from the rest of the BVIs. Unlike the volcanic, hilly islands, Anegada is completely flat and largely unpopulated, boasting some of the most amazing white sandy beaches you'll ever see, and an incredibly casual, relaxed vibe.
Once you grab a mooring ball off of Setting Point and go ashore, your first order of business should be to pick the color of the Moke you want to rent from one of the local shops. You could also opt for a pickup truck with bench seating in the back if you have a larger group. Either option provides you the freedom to explore and (try to!) get lost on the island – though that's almost impossible, as there's basically one main road that circles the island. We always make sure to check out the charming pink flamingos in the middle of the island – they’re a delight! There are a number of fantastic beachside cafes and bars where you can easily spend a lazy afternoon. Our personal favorite is Tipsy by Ann on Cow Wreck Beach, but honestly, you can’t go wrong at the Anegada Beach Club or The Big Bamboo Beach Bar.

Don’t fill up too much on those afternoon snacks, though, because you have a truly great dinner ahead. Anegada is world-famous for its grilled spiny lobster, and it is absolutely amazing. Now, this might get me into trouble back home since I live in Maine, but I honestly think it’s even better than the lobster in my home state! There are a number of fantastic restaurants right on the beach near your boat to choose from. The Wonky Dog is our personal favorite, but we haven’t had a bad experience at any of them. Just make sure you call the restaurant in the afternoon and place your lobster order – it’s a custom that ensures your fresh catch is ready for you! We actually enjoy spending two days at Anegada because it truly is the epitome of Caribbean relaxation for us. If you are looking for more to do on a second day, you could take a tour of Conch Island or even try your hand at spear fishing for bonefish (good luck – they're fast!).

Regarding St. John's in the USVI: St. John's in the US Virgin Islands is incredibly close to the BVIs – you’ll definitely see it from several points – and it seems so easy to just shimmy on over and pop into one of the amazing bays on the island with unbelievable snorkeling. However, we want to give you our honest opinion: it's not as easy as it looks. The challenge is that you need to formally clear out of the BVIs and enter the USVIs, and then do the same in reverse on your way back. This involves time-consuming paperwork, using mobile apps, and stopping at customs offices to pay fees, which, to us, doesn't sound very vacation-like! Personally, we would stick to exploring the BVIs to the fullest and then, on a separate trip, come back and charter a boat for another week strictly in the USVIs! Trust us, there is plenty to keep you busy and delighted in both places. We’ve done both ourselves, and this approach truly maximizes your relaxation time.

Life Aboard Your Catamaran: What to Expect from Your Floating Paradise

One of the most common questions we get is, "What's it really like to live on a catamaran for a week?" It's an experience unlike any other, offering freedom and intimacy that resorts simply can't match.

Your Comfortable Floating Home: Moorings catamarans are designed for comfortable living. While the cabins are not massive, they are incredibly well-appointed and cozy, each with its own private head (bathroom). You'll find them to be a perfect retreat after a day of sun and sea. The living spaces – both inside the salon and especially out on the spacious deck – offer plenty of room to stretch out, relax in the shade, or soak up the sun. Imagine swimming and snorkeling right off the stern anytime you wish – no crowded resort pools here! The rhythm of life on a catamaran is inherently relaxing.
Eating: A Delicious Rhythm (Including Provisioning!): We typically recommend enjoying breakfast and lunch on the boat. This is easy to do with your provisions, offers flexibility, and often comes with the best views! Dinners are usually enjoyed out at the various beach bars and restaurants on the islands, giving you a chance to experience the local cuisine and vibrant nightlife. This balance works perfectly.
Now, let's talk about provisioning – stocking your floating pantry! This is a major activity that ensures you have everything you want on board for the week, including all your food and beverages. Moorings has a fantastic service that allows you to provision ahead of time, and they'll have everything delivered directly to your boat. We've definitely taken advantage of this convenience, as it's a huge time-saver and ensures your fridge is full upon arrival! However, we also love making a quick visit to the nearby supermarket for any last-minute cravings or forgotten items – it’s part of the pre-sail excitement. Having all your favorites on board makes onboard dining incredibly easy and enjoyable.
Wi-Fi on Board: Don’t worry, you will still be connected to your loved ones back home as there is Wi-Fi available on the Moorings catamarans. Feel free to let everyone know what they’re missing!

Your Dinghy: Your Island Shuttle: Your trusty dinghy, the small motorized boat kept on board, truly becomes your "car" to shore and back. It's how you get to those beach bars, restaurants, or simply explore a secluded cove that’s too shallow for the catamaran. It’s also a lot of fun to learn how to drive. And here's a tip from our own experience: at night, when you're returning on your dinghy from dinner, it can be very difficult to find your catamaran among all the others in the bay. We've found that hanging up some twinkle or Christmas lights around the catamaran, brought from home, makes it so much easier and festive!

Help as Much (or as Little) as You Wish: If you've hired a captain, your participation is entirely up to you. You can sit back with a book and a cocktail, or you can get involved! You can help out with picking up mooring balls, raising or taking down the sails, or learning about navigation. It’s entirely your choice.
Activities Galore (Right Off Your Deck!): From the moment you wake up until the sun sets, there are endless ways to spend your days. It’s incredibly easy to go snorkeling, try your hand at fishing right off the boat, or enjoy paddleboarding and kayaking in calm bays. Or, if you prefer, simply sit and do nothing at all but read a good book.
Post-Dinner Fun: Our Evening Rituals: Evenings on the boat, especially if you’re with a group of friends, are just as memorable. Post-dinner fun typically includes some form of impromptu dance party under the stars, competitive (or not-so-competitive!) card games, and, of course, delicious cocktails made from your onboard provisions. These are some of our favorite memories from our BVI trips.

Conclusion: Your Unforgettable BVI Catamaran Dream Awaits!

The British Virgin Islands, explored by catamaran, offer an experience that’s truly unparalleled. It’s a perfect blend of adventure and relaxation, stunning natural beauty and vibrant local culture. From navigating the Sir Francis Drake Channel to discovering hidden grottoes and enjoying world-famous beach bars, every day brings a new discovery.

For us, it's more than just a vacation; it's a re-connection with the sea, with friends or family, and with a profound sense of freedom. We hope our personal insights and recommended itinerary have inspired you to consider this incredible way to experience David's happy place. We truly believe it's one of the best adventures you can have anywhere in the world and we at Jetsettery are happy to share our personal knowledge and make this dream a reality for you. Catamarans book quickly so let’s start planning now!

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