Leeward Island Yacht Charters

British Virgin Islands are located in the Leeward Islands

Your yacht charter will allow you the freedom of a leisurely cruise around the magnificent fjords and coastal inlets. Stunning beaches, world-class snorkeling. The northern islands of the archipelago are more sheltered and it is rumoured that the early British explorers called them the Leeward Islands.

Situated where the Northeastern Caribbean Sea meets the western Atlantic ocean, the Leeward group of islands reach from Dominica, just above Martinique, and arc gently northwest for just under 150 miles to include the U.S. Virgin Islands, the British Virgin Islands, Anguilla, Saint Martin, Saint-Barthelemy, Saba, Sint Eustatius, Saint Kitts, Nevis, Barbuda, Antigua, Redonda, Montserrat and Guadeloupe. They end near St. Martin 150 miles east of Puerto Rico.

The Leeward group of islands and its waters are a popular destination for a comfortable, relaxing, gorgeous Caribbean charter yacht adventure.

Find the perfect yacht for your Charter Yacht holiday in the Leeward Islands, Caribbean!


The British Virgin Islands

Chartering a yacht to explore the British Virgin Islands will reveal a satisfying pace of life that will nourish the soul. Working with Crewed Charter Vacations and our crew, we will make every effort to ensure that your experience not only meets but completely surpasses your expectations.

Apart from the opportunities, the Caribbean ocean’s playground provides, as well as the obvious world-class snorkeling and diving, each island of the British Virgin Islands has a unique characteristic, from the culture and history of the British Virgin Island’s four largest islands to the pristine natural beauty of its many smaller isles. The splendor that greets, every time you drop anchor, is what makes the Caribbean, and the British Virgin Islands a most remarkable and truly unforgettable charter yacht destination.

As you discover each island’s treasures you will be spoilt for choice, and all or nothing of what you choose to do will be your own.

Good news! The West End Ferry Terminal has finally resumed its operations on August the 01st to welcome ferry vessels from the United States Virgin Islands (USVI’s) and other international destinations.


Islands in the British Virgin Islands

The British Virgin Islands consist of the main islands of Tortola, Virgin Gorda, Anegada, and Jost Van Dyke, along with over 50 other smaller islands and cays. About 15 of the islands are inhabited. Road Town is the capital and is situated on Tortola, the largest island. Tortola is about 12 miles (20km) long and 3 miles (5km) wide and has a population of just under 25,000 permanent inhabitants.

The permanent inhabitants of the British Virgin Islands are British citizens. Although the territory is not part of the European Union and not directly subject to EU law, British Virgin Islanders are deemed to be citizens of the EU by virtue of their British citizenship.

The first settlers of the Virgin Islands were the Arawak people from South America around 100 BC. The Arawaks inhabited the islands until the 15th century when they were succeeded by the more aggressive and powerful Caribs, a tribe from the Lesser Antilles islands. The Caribbean sea is named after the Carib tribe.

Christopher Columbus and his expedition were the first westerners to discover the British Virgin Islands in 1493 on their second voyage to the Americas. Columbus gave them the over-imaginative name Saint Ursula and her 11,000 Virgins, shortened to The Virgins, after the legend of Saint Ursula.

The Spanish Empire, therefore, claimed the islands by discovery in the early 16th century, but never settled them, and subsequent years saw the English, Dutch, French, Spanish, and Danish all jostling for control of the region, which was fast becoming a notorious haunt for pirates. The Dutch had established a permanent settlement on the island of Tortola by 1648. In 1672, the English captured Tortola from the Dutch, and the English annexation of Anegada and Virgin Gorda followed in 1680. Meanwhile, over the period 1672–1733, the Danish gained control of the nearby islands of Saint Thomas, Saint John, and Saint Croix.

The British Virgin Islands were considered principally a strategic possession, but slowly it’s economic viability was discovered and crops were planted. The British introduced sugar cane which was to become the main crop and source of foreign trade, and a large number of slaves were brought from Africa to work on the sugar cane plantations. The islands prospered economically until the middle of the nineteenth century, when a combination of the abolition of slavery in the territory, a series of disastrous hurricanes, and the growth in the sugar beet crop in Europe and the United States significantly reduced sugar cane production and led to a period of economic decline.

Leeward Island Yacht Charters
British Virgin Islands Yacht Charter Vacations
Leeward Island Yacht Charters Destinations

British Virgin Islands

This one-week itinerary is designed to maximize your time spent enjoying your fabulous charter yacht, as well as experiencing the remarkable magic of the British Virgin Islands. Overnight anchorages in the most exquisite and secluded coves of uninhabited islands, balanced out with spectacular attractions and a good taste of local cuisine, unforgettable cocktails and more fun than you can handle.

After arrival and welcome by your charter yacht crew, you will have a chance to settle in before setting sail to a nearby cove where lunch will be served and you will spend the night at anchor. Enjoy your first few hours on your charter yacht, lazing on deck, swimming, snorkeling or taking advantage of the many onboard toys and activities. Settle in for an evening of scrumptious local cuisine served by your crew, and sip on a special cocktail of your choice while you relax in comfort on the spacious flybridge with 360-degree views of the spectacular islands.

After breakfast, we set off on an easy sail through the Sir Francis Drake Channel to Norman Island. This area is known for some of the best snorkeling spots in the British Virgin Islands. You can snorkel at the Indians, a dramatic series of rocks jutting out of the sparkling cerulean waters approaching Norman Island, or the legendary Caves. While away the afternoon and settle into the laid back island rhythm, enjoy another meal onboard specially prepared by your personal chef, or head ashore to Pirates Bight restaurant to watch the sunset and catch some island vibe.

We haul anchor and begin a gentle sail northeast from Norman Island to Peter Island, with a swim and a snorkel at any one of the 5 paradise beaches. Deadman’s Beach is stunning and is a favorite for swimming with the sea turtles or hang out with these gorgeous creatures on your paddleboard or kayak. There is often enough surf to enjoy the waves or soak up some rays on the white sand beach. The uninhabited National Park island of Dead Chest is a large rocky outcrop located just under a one-half mile northeast of Deadman’s Bay on Peter Island and is a popular scuba diving and snorkeling site. If you fancy something a little more lively, head around for some entertainment at the new Willy ‘T’ floating bar and burger joint, which is now back at its original location in The Bite, Norman Island. A more tranquil alternative is Little Harbour, here, the underwater lights will attract stingrays and huge tarpon who will put on a glorious show in the crystal clear waters.

Day four will begin shortly after breakfast as we set sail and pass by Salt Island, which is aptly named after its salt ponds, which were once an important resource. Salt Island is also the location of the famous RMS Rhone wreck, the Royal Mail packet steamer which sank in a hurricane in 1867. The stone gravesite where her victims were buried is still there today, just a short walk from the main beach. The wreck of the Rhone is one of the best scuba diving sites in the Caribbean. Close by, Cooper Island, is home to a popular beach bar and restaurant, with a dive shop, boutique and Rum Bar positioned in Manchioneel Bay. The stunning sand bottom blue Chromis Reef, named after the blue chromis fish, features numerous corals with sea fans, gorgonians, quillfin blennies in abundance. Exploring the reef is a must for those that want to experience the majesty of this natural wonder. It is a deep dive spot, but ideal for training, since the visibility is so good.

Not very much further along we will sail past the privately owned Ginger Island which rises gracefully from the sea, surrounded by luscious mangroves. And beyond the hilly landscapes of Ginger Island you will see Virgin Gorda, famous for her ‘natural baths’! A fabulous spot to spend the night is Long Bay, Virgin Gorda. An early anchorage allows for plenty of time to either swim to shore to explore The Baths, which are a stunning set of pools in amongst boulders of various shapes and sizes, or tender across and enjoy the hike to get to them.
The laid-back pace of the island is the perfect excuse to take your time, whether you’re wading along the granite grottoes of The Baths, doing some casual snorkeling in Devil’s Bay, exploring the stone ruins of a 19th century Copper Mine, or hanging out on a hammock sipping an ice cold Caribbean cocktail.

Early morning set off from Long Bay, after another delicious breakfast, should get you to Anegada by late afternoon. This lengthy and exhilarating sail will still allow time to stop at some more of the Caribbean’s underwater paradises, such as ‘The Dogs’, for a swim and snorkel, and there are a number of great scuba diving spots here as well. The idyllic Eustatia Sound, is a wonderful place for lunch, another swim or snorkel and you’ll want to photograph the surreal turquoise seas and white beaches that surround you. From here it is another two-hour glorious sail to Anegada, the low lying coral atoll famous for its pristine beaches and pink flamingoes! There’s plenty of fascinating sea life, dolphins and flying fish are known to join us on this leg of the journey, and even humpback whales when in season.
On arrival at Anegada, there’s plenty to choose from for dinner: the Wonky Dog, Potters by the Sea and the Lobster Trap are all restaurants that come highly recommended for a truly Caribbean experience.

Here you have the option to spend a little more time in Anegada, which we highly recommend. You could possibly hire a car, or a scooter to allow you some ‘solo’ unlimited discovery. Anegada is the only inhabited British Virgin Island formed from coral and limestone, rather than being of volcanic origin, it may be flat, but it’s diverse and there is certainly lots to explore. Anegada is known for miles of white sand beaches and the 18-mile-long Horseshoe Reef, the largest barrier coral reef in the Caribbean, and the fourth largest on earth. You can happily spend some time here…
Apart from the gorgeous white sand beaches, you can explore the 18-mile-long Horseshoe Reef, the largest barrier coral reef in the Caribbean, and the fourth largest on earth. Surrounded by shallow coral reefs, Loblolly and Cow Wreck beaches are favorites, both have great restaurants for lunch, and the Anegada Beach Club is excellent. If you’re up for exerting a bit more energy, Tommy Gaunt Kitesurfing School is also situated at the Anegada Beach Club, you can hire or take lessons if you’re not too familiar with kite surfing. Either way, it’s a lot of fun…

Another stop, could be Marina Cay, or nearby Bellamy Cay – an island located entirely within Trellis Bay on Beef Island. Or even Guana Island, one of the few remaining privately owned islands in its part of the world. Guana has seven white powder-sand beaches and 850 acres of tropical forest, mountains, hills, and valleys. The island is mostly natural preserve and has a small resort.

A chilled downwind sail to White Bay, on Jost Van Dyke is on the itinerary today. Some might say this is ‘saving the best for last’… Jost Van Dyke one of the British Virgin Islands most popular destinations, and there are many good reasons for that. Located right on the beach in White Bay is the Soggy Dollar Bar, famous for its ‘Painkiller’ rum-based cocktail. Other exceptional Soggy Dollar Bar antics include playing “hook the ring”, or you might enjoy a “cheeseburger in paradise” and flick through their amazing book about the rebuilding after Irma. White Bay is lined with beach bars and is a very popular stop for yachts and boaters from Tortola, St. Thomas, and St. John. It’s pristine white beach is fabulous for sunning yourself, swimming or snorkeling … or take a stroll and enjoy the fine white sand between your toes.

On the east side of Jost Van Dyke, Foxy’s Taboo is a locally famous lunch restaurant, bar, and gift shop. A dock is available for day boaters. Nearby, a natural rock formation called the bubbly pool is a popular attraction. It gets its name from the bubbles that form in the water when waves crash against the rocks.

As the sun begins to set, head over to Great Harbor for dinner at Corsairs and dancing late into the night at the famous Foxy’s. If Foxy isn’t playing his guitar, he can often be found in the restaurant and is happy to take a picture with you.

After a last swim in the pristine Carribean waters, with a happy heart and possibly slightly ‘foggy’ head, filled with great memories and new friends, we set sail back to Tortola where your time on your charter yacht will come to an end, until the next time!

Please note, this is a sample itinerary designed to whet your appetite and by no means depicts your expectations or limits available options. Crewed Charter Yacht Vacations will work with you to ensure your IDEAL itinerary is finalized.

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Famous for its warm climate, breathtaking beaches, and epic yachting events, Antigua is one of the Caribbean’s premier tourist destinations. Antigua offers charter yacht guests a myriad of explorative opportunities, from coves and inlets to its nearby uninhabited tropical island paradise offering excellent snorkeling and a variety of secluded beaches.
Antigua Yacht Charters
Antigua Crewed Yacht Charter Vacations


Antigua is one of the Leeward Islands in the Caribbean region and the main island of the country of Antigua and Barbuda. The island’s circumference is approximately 87km and has a population of a little over 80,000, with over 32,000 people living in the capital city, St. John’s.

This one-week itinerary is designed to fully explore the Antigua and Barbuda by circumnavigation on your charter yacht. An ideal itinerary if you’re looking for the best of both worlds; land and sea!

After arriving in Antigua, and being transported to your charter yacht, you will be met by your crew and welcomed aboard with a delicious refreshing Caribbean beverage. A safety and orientation briefing will be given and you will then set sail to a nearby cove where lunch will be served and you will spend the night at anchor.

Enjoy the afternoon swimming, snorkeling and getting to know your charter yacht and crew. Settle into the laid back island flow while taking it all in and unwind before being presented with your first fabulous meal prepared by your highly trained crew.

Day two of your charter is an easy sail northwards to Deep Bay. The very vision of an idyllic Caribbean beach, the white sands, and palm trees create the ideal backdrop for a day of relaxation. Deep bay offers a fantastic opportunity for snorkeling the wreck of The Andes, a merchant ship that caught fire and sank offshore in 1907 which now rests in the shallow waters. Its coral-encrusted mast can be seen protruding from the water in low tide. As you’d expect, the wreck is home to a plethora of fascinating and colorful sea life and is a wonder to explore. Your crew could prepare another scrumptious meal, or you could head across to Fort Barrington for a delicious restaurant meal, or take a short hike up to the fort through the Manchioneel trees. Today the remains of Fort Barrington include a powder magazine and two gun platforms that held eight guns as well as providing magnificent views of St. John’s Harbour and Deep Bay. After lunch, find a comfortable seat on the foredeck as we sail north to Barbuda which is home to the Frigate Bird Sanctuary, located in the Codrington Lagoon. Enjoy a tour of the bird sanctuary followed by fresh lobster or fish for dinner, and enjoy a stunning sunset while anchored at Low Bay.

After a delicious breakfast, spend a few more hours exploring Barbuda’s gorgeous wild beaches full of driftwood and shells, and make your way around to the other side of the island with its pink sand beaches which are perfect for swimming and snorkeling. There’s plenty of opportunities to see turtles, rays, sharks, barracuda and many other varieties of tropical fish in the turquoise water.

Barbuda is also a paradise for birdwatchers who come to see the Frigate birds and many other rare species including Ospreys, Whistling Ducks, Tropicbirds and the yellow Barbuda Warbler – known locally as the Christmas Bird and the only one of its kind in the world!
An alternative to Barbuda (or in addition if time allows it) is Great Bird Island. An idyllic setting with its white sand beaches lined with palm trees and populated by exotic wildlife and makes Great Bird island the quintessential vision of paradise. A short hike will take you to the perfect vantage point of the surrounding islands, and the marine life is worth checking out below the sea surface.

We set sail for Green Island and Nonsuch Bay, with a good chance of spotting a fever of stingray in their natural environment. We can organize a tour where the participants may have the opportunity to feed, touch, and interact with the wild creatures under supervision. After a thrilling experience with the stingrays, and scrumptious lunch we continue to Nonsuch Bay on beautiful Green Island. There is plenty of room in Nonsuch Bay for anchoring and the windward reef offers protection from the sea. Nonsuch Bay is home to Harmony Hall; an art gallery and Italian restaurant set high overlooking the bay. Enjoy cocktails in a converted sugar mill. Nonsuch Bay is also home to Nonsuch Bay Resort, and dinner reservations can be made at this wonderful waterfront resort. You could also try kite surfing and the snorkeling here is excellent.

Today we set off after breakfast for our downwind sale towards English Harbour, a Caribbean sanctuary, rich in maritime significance and naval history. The main entrance to the protected natural harbor is flanked by fortresses on either side, transporting you back in time to the 18th century when the Royal Navy’s Caribbean fleet was first established there. Not far from Nelson’s Dockyard, English Harbour has plenty to offer travelers of all kinds including an array of bars and restaurants, and an English pub that offers a British menu with a Caribbean twist. There is also duty-free shopping, a museum highlighting the local history of the land, and “jump up” steel band sessions that will have you bopping and clapping along.
We will spend the night anchored at Freeman’s Bay, a breathtaking, hidden away, tropical paradise with splendid snorkeling conditions.

Spend the day relaxing, exploring the charm of English Harbour a little further, or take a walk to Falmouth Harbour for a horse ride on the beach. If you’re still up for some water activity, there is plenty to be had, from diving to snorkeling, swimming or kite surfing. You will not be bored as there is plenty to see and do at this end of the island.

After a leisurely breakfast, we continue our downwind sail, past Cades Reef onto 5 Islands, Pinching Bay or perhaps Hermitage Bay, all of which are exceptional anchorage options. We would spend the day and evening enjoying the serenity and beauty of Antigua. Perhaps beach games or try your hand at using the Stand Up Paddleboards…relax on one of our floating sun lounges or simply relax on the foredeck of SV Callista, under the shade with a book and ice cold beverage while listening to your own personal music through speakers on the foredeck.

After breakfast and a last swim, we will set off on the final short leg of your fabulous charter yacht journey to Jolly Harbour Marina where you will leave us with happy hearts, a head full of memories and a promise to return. Until next time!

Please note, this is a sample itinerary designed to whet your appetite and by no means depicts your expectations or limits available options. Crewed Charter Yacht Vacations will work with you to ensure your IDEAL itinerary is finalized.
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