Top Sailing Itineraries: British Virgin Islands

/ Published in British Virgin Islands

Top Sailing Itineraries: British Virgin Islands

The sailing season in the BVI is one of the longest in the world, giving new and seasoned sailors ample opportunity to explore the renowned Caribbean waters in our award-winning destination

Thanks to the subtropical climate, you can sail the BVI year-round, except for a few months in late summer/early fall during “hurricane season”. While the British Virgin Islands have not taken a direct hit from a hurricane since 2017, our Tortola base is closed from mid-August to early October and all boats in our fleet are taken out of the water as a precautionary measure. 

For most of the year, the sailing conditions in the BVI are extraordinary, with hot summers and warm winters. The high season for sailing the BVI is December through March with mid-day temperatures consistently reaching into the 80s. The summer features hotter temperatures and a slightly higher chance of rain, but the sailing conditions are otherwise phenomenal. 

Pro Tip: Most of our BVI catamarans are newer models that come with air conditioning, so be sure to check for that feature when booking the hotter summer months for optimal comfort aboard.

Regardless of the time of year you decide to sail, this article will lay out two of our charter guests’ most popular sailing itineraries for the BVI. Get ready for our top sailing tips, let our team of experts help you book your yacht, and start planning your next award-winning yacht charter today!

Both of our featured BVI sailing itineraries are for 6 nights (7 days), but they can easily be adjusted to fit a longer or shorter trip. If you don’t want to follow these itineraries completely, just view them for inspiration when you plan your BVI sailing trip, and use this article for ideas about places to visit and things to do. If you add a professional skipper to your booking, they can help you plan an unforgettable sailing route with a local touch, based on the length of your trip, preferences, and priorities. You can still use the sample routes below as your starting point. 

If you’re seeking the highest level of luxury and service and want to experience the ultimate exclusive vacation, we now offer our luxury crewed charter in the BVI onboard the beautiful Valinor. It’s the perfect opportunity to enjoy these sailing itineraries in extraordinary opulence while adding a few extra layers of luxury to your experience.  


Itinerary 1: Snorkeling Adventures and Island Hopping Extravaganza

With stops at Norman Island, Cooper Island, Beef Island, Virgin Gorda, Jost van Dyke, and Peter Island.

Sailing Itinerary 1

Day 1: Norman Island

On the first day, sail from our base in Road Town, Tortola, to The Bight, Norman Island. It’s the ideal place to start your Caribbean journey with sheltered anchorages, seaside restaurants, and the perfect place for water sports, swimming, and relaxing. 

We recommend a stop for drinks or a quick lunch at the popular Willy T, which is a floating restaurant onboard a ship. Just take your dinghy or swim over! If you are looking for a dinner spot in the area, a great choice is Pirates Bight, a beautiful, ambient restaurant located right on the beach with a perfect view of the sunset. You may have to reserve a table in advance as it’s unsurprisingly a popular place. The overnight anchoring spot is in the Bight. 

Day 2: Snorkeling and Cooper Island

While still on Normans Island, make a stop by the Caves for some snorkeling and you have the chance to see corals in addition to a variety of fish and wildlife. Then sail over to the Indians, a famous site featuring impressive rock formations in the water. This is another excellent snorkeling place as it’s teeming with sea life. If you haven’t had enough of underwater exploration, you can also stop by the famous shipwreck of The Rhone. Whether you go snorkeling on your own or book a diving tour with a guide to see the wreck up close, it’s worth a visit. 

Your anchoring spot for the night is in the beautiful Manchioneel Bay on Cooper Island where you can watch the sunset from the deck of your charter boat while you savor a delicious dinner onboard. 

Day 3: The Baths and Trellis Bay

Start the day by sailing to Virgin Gorda, which is home to the spectacular “The Baths” and arguably one of the coolest beaches in the world. The Baths is a must-visit if this is your first time in the British Virgin Islands. 

Then, sail over to Trellis Bay on Beef Island for the night where you can pick and choose among a variety of seaside restaurants and beach bars and enjoy the lively nightlife. Trellis Bay is known for its beach party celebrations, such as the monthly full moon party. 

Day 4: Dog Islands and Virgin Gorda 

As you head over Sir Francis Drake Channel again towards the north part of Virgin Gorda, make a stop by the Dog Islands on the way, where you can explore more underwater life or simply enjoy the rare sight of untouched nature. 

Continue to the north coast of Virgin Gorda and you will find many popular restaurants for a delicious dinner by the sea, for example, the restaurant at Leverick Bay which features a pirate theme, or the beautiful waterfront restaurant at the Bitter End Yacht Club. A third option is Saba Rock Resort, located on a small island north of the Bitter End Yacht Club. 

Before dinner, go and explore the area and try to spot some turtles here. You may also just relax on a beach or do some water sports activities if there is time. 

Day 5: Guana Island and Jost van Dyke

Prepare for the longest sail yet as you start your journey towards Jost van Dyke. About halfway there, you will discover Guana Island and the southern tip of it known as Monkey Point. It’s a perfect place to stop for lunch onboard the yacht. Anchor in the bay for a while as you enjoy the white sandy beaches and the gorgeous nature, then continue your sailing journey towards your destination. 

Jost van Dyke is home to some of the most iconic beaches of the British Virgin Islands, the most well-known one being the beach in White Bay where the famous Soggy Dollar Bar is located. The Soggy Dollar is where the drink called Pain Killer originated, so if you want to try the original version, this is the place to go. After the drink, finish the day off with a sunset dinner on the beach at one of the beach restaurants or enjoy a meal onboard your yacht. 

Day 6: Soper’s Hole Marina and Peter Island

On your last day of sailing, it’s time for some souvenir shopping. Soper’s Hole Marina is perfect for that, and it’s on the way from Jost van Dyke to Road Town anyway. Walk the streets, do some shopping, or go for ice cream. 

If you still have some hours to spare, you can take a trip to Deadman’s Bay (Peter Island) for a last glimpse of the Caribbean beauty. Great Harbour (also Peter Island) is a good place to anchor for the night. 

Day 7: Tortola

Now it is time to head back to Road Town, Tortola, where our base is located. Disembarkation needs to be done by noon, so make sure you leave early and have enough time to fill up the fuel tanks when you return. 

Itinerary 2: Exploring the Caribbean's Distant Wonders (including Anegada)

With stops at Virgin Gorda, Anegada, Beef Island, Jost van Dyke, and Norman Island.

Day 1: The Baths and Spanish Town

Start your Caribbean journey by sailing east to The Baths, possibly the most iconic beach in the British Virgin Islands. The Baths feature rock formations that come together with the blue water and fine sand to form a postcard view of rare Caribbean beauty. On land, the rock formations create a maze-like structure with hiking trails inside of it. If you decide to make the hike to the top, you will find a restaurant (Top of the Baths) with a good view of the island. Heading south will take you to the beautiful Devil’s Bay National Park.

A brief sail northward ends at Spanish Town where you can enjoy some shopping and an array of dining options or settle for a nice dinner onboard your yacht with a sunset view.

Day 2: Virgin Gorda

Enjoy the scenic sail along the west coast of Virgin Gorda as you make your way to Gorda Sound. The various bays in Gorda Sound are great places for swimming, kayaking, paddle boarding or just relaxing on a beach or on the deck of your yacht. 

As the sun begins to set, find a seaside restaurant to savor the last hours of the day with a delicious meal and a spectacular waterfront view. There are several good restaurant options in this area such as the Restaurant at Leverick’s Bay, the Bitter End Yacht Club, and Saba Rock Resort

Day 3: Anegada

It’s time to make the longest sail of the trip, to Anegada. Located in the open sea about 15 miles north of Virgin Gorda, it’s the most remote of the British Virgin Islands. The sail alone is quite memorable as you’ll be surrounded by blue water on all sides and feel the wind in the sails. 

If you are a nature enthusiast, a diver, or a seafood lover, Anegada is a must-visit. This unusual island is made of coral and limestone. Surrounded by several underwater coral reefs and more than a few shipwrecks, this place is a paradise to explore for divers. 

Anegada is also famous for its lobster, so we recommend a lobster dinner or lunch at one of the waterfront restaurants while you’re here (we can recommend the Lobster Trap). Usually, the chefs cook the lobster right on the beach not far from where it’s been fished, which makes for a culinary experience unlike any other. 

Day 4: Beef Island

Sail from Anegada to either Guana Island or Scrub Island, where you can stop for some mid-day fun in the sun, and then make your way to Beef Island. It’s a day for exploring, island hopping, water sports, snorkeling, and relaxing beneath the warm sun. 

End your day at Trellis Bay on Beef Island. Trellis Bay is known for its nightlife on the beach, the most notable celebration being the full moon party. Have a drink and a local meal at a beach bar or enjoy a lovely sunset dinner onboard your yacht. 

Day 5: Jost van Dyke

Sail to Jost van Dyke where you can go for a hike in the lush hills above Great Harbour and enjoy the white sandy beaches. It’s a fun place, perfect for swimming and relaxing with a tropical drink in your hand. Why not try the famous Painkiller drink while you’re here? The Soggy Dollar Bar is the place where the drink originated back in the 1970s. Finish off the day with a delicious dinner by the sunset at one of the beach restaurants.

Day 6: Norman Island

The waterway between Tortola and St. John is known as The Narrows. On Day 6, you’ll travel along The Narrows, between Great Thatch Island and Mary Point, then follow the coastline of St. John in the southeast direction before eventually heading straight south towards Norman Island. 

Norman Island is a beautiful sailing destination with secluded bays and coves perfect for watersports, swimming, snorkeling, and enjoying the scenery. This place is said to be the inspiration behind the famous “Treasure Island” written by Robert Louis Stevenson. 

Besides some great bars and restaurants (including the floating bar Willy T and the beach restaurant Pirate’s Bight) you will also find an excellent snorkeling spot here known as the Caves and it’s only a short trip from the Indians, another famous place for underwater exploration. 

Day 7: Tortola

On the last day, you can head back to the base early for more time to explore Tortola or make one last stop at Peter Island for a last opportunity to bask in the Caribbean beauty. Just remember to leave well in advance so you have enough time to fill up the fuel tanks before disembarkation, which must be completed by noon. 

While there are so many beautiful places to visit during your yacht charter in the British Virgin Islands, unfortunately, everything won’t fit into a one-week itinerary. Having to prioritize and choose when it comes to any itinerary can be difficult, so we wanted to lend you a helping hand. We hope these sample sailing routes will inspire you when you plan your vacation.

Whether you follow one of these top-rated sailing itineraries or only draw some ideas and inspiration from them, we have built itineraries based on our charter guests' favorite places to visit and things to do. We hope you will enjoy them too! 

Since 2001, over 350,000+ charter guests have set sail with Navigare - it’s safe to say that your yachting adventure will be in capable hands. With 12 exotic locations worldwide, the possibilities are endless! Whether you're an experienced sailor or a first-time adventurer, Navigare Yachting opens up a world of exploration, discovery, and sailing that comes with complete peace of mind.

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