Written by Missy Johnston

sunset on the island of Virgin Gorda, BVI

Beautiful Sunset on Virgin Gorda in the BVI’s

A warm Caribbean adventure in winter will cure even the deepest cold-weather blues. Frommers calls the winter climate from Puerto Rico south a “perpetual May,” averaging between 75°F and 85°F. In the islands, winter is also the dry season, with only the occasional shower. In other words, you can look forward to near-perfect conditions for your winter in the Caribbean chartering a yacht.

Not only that—the main sailing season in the Caribbean begins in November and ends in July. The primary high season runs from mid-December through to the end of May. Anyone searching for a warm-weather getaway chartering a yacht from either Europe or North America will be delighted by the tropical, storm-free conditions.

The weather is only the first great reason to book a private yacht charter this winter in the Caribbean. You can find the perfect hotspot for yourself and your family based upon the things you love to do and the type of exploration that appeals to you. The following is everything we like about all of our favorite places, along with a little on the appeal of spending the holidays in the islands. Finally, we will detail average private yacht charter pricing for a Caribbean yacht charter.

Caribbean Yacht Charter Winter Hotspots

What is a good winter yacht charter destination? These are our favorites:

The British Virgin Islands

The Baths

The Baths, Virgin Gorda

Fifteen islands in a 15-mile diameter make up the pristine British Virgin Islands, a territory considered virtually unspoiled. Calm protected waters and dozens of anchorages greet the average yachting enthusiast. Visit Anegada to see the deserted beaches and the unique flora and fauna of its salt ponds, home to the pink flamingo. Go snorkeling amongst the giant boulders of the Baths on Virgin Gorda. Enjoy the long sandy beach of Cane Garden Bay, and stop in at the Soggy Dollar Bar, home of the original Painkiller Cocktail at Jost Van Dyke. Anchor in the Bight on Norman Island, where pirates used to hide, and snorkel or scuba dive on the Wreck of the Rhone—the “other unsinkable ship” built at the same time as the Titanic.

St. Maarten and St. Martin

Beautiful Waters of St. Martin

Beautiful Waters of St. Martin

Experiencing these two halves of the same island is a remarkable opportunity. Legend has it that the French and the Dutch each walked from their ends of the isle to reach the boundary that would split the territory between the two nations, but as both sides were drinking, the French—always the more polished drinkers—walked faster and covered more ground.

Visit French St. Maarten for seclusion, chic shopping, restaurants, and beautiful beach bars with seating in the sand. Dutch St. Martin boasts duty-free shopping and buzzing nightlife, including flashy casinos.

St. Barts

Eden Roc Hotel St Barths

Eden Roc Hotel

Gustavia in St. Barts is a bustling harbour with a very French feel. European architecture and trendy boutiques line the streets. High-end nightlife and top French restaurants make this port très chic. The feeling overall is festive and somehow quaint at the same time. Enjoy a long lunch at Nikki Beach Restaurant or the restaurant at the Eden Roc Hotel, which overlooks one of the most popular beaches on the island. There are many more beaches; you can see the most secluded ones from your yacht and can often enjoy an entire tucked-away beach all to yourselves.

St. Kitts

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St. Kitts Sugar Cane Fields

Visit St. Kitts if only for the stunning views from Brimstone Hill Fortress, or the antics of the green vervet monkeys. They were brought to the islands in the 1800s by French plantation owners and have charmed and amused visitors ever since. The old sugar cane train takes you through the fields and by the ruins of plantation homes and sugar mills—a truly unique landscape.


Antigua English Harbor Nelson's Dockyard Old Sail Loft Boat Hauling Area

Nelson’s Dockyard

On the island of Antigua, head to Nelson’s Dockyard, part of a UNESCO World Heritage Site. This beautiful harbour is where quite a few private charter yachts spend the winter. Many of the original buildings and fortifications built by the British Royal Navy, created from coral block, are still standing, some said to be haunted by sailors from long ago. The former naval yard now boasts hotels, restaurants, museums, little boutiques, and more. Sailing into Nelson’s Dockyard as ships have done since the 1700s and coming in stern along the dockyard walls originally laid by Nelson’s men provides that extra little bit of magic.

Tobago Cays

Caribbean, Luxury Yacht Charter

Green Sea Turtle

The Tobago Cays Marine Park invites snorkelers to play in warm, sparkling blue-green waters, and see green and hawksbill turtles at the turtle sanctuary. Scuba divers can dive a wrecked British gunship and the coral gardens. On land, have a picnic on beaches used in filming Pirates of the Caribbean. Enterprising locals may come by to sell lobsters to your chef for an onboard Caribbean lobster dinner.


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Bequia Whale Bone Jaws

Bequia is a fascinating port. As its own nation with fewer than six thousand permanent residents, it boasts a distinct ambiance. In the 1800s, a native left to learn the whaling trade in New England and returned to teach the locals. Today, Bequia is one of the few locations allowed to hunt a small number of whales per year, a number that they rarely meet. Lookouts are posted every day and a small team trained in whale hunting is always standing by to jump into shallow-hulled fast-sailing skiffs designed and built on the island to hunt whales by hand with handmade harpoons. Residents are also known for their artistry work carving ship half hulls for display.

A Caribbean Winter Yacht Vacation Holiday

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Caribbean Sunset

Does the idea of digging your toes into the sand on a warm New Year’s Eve appeal to you? The holiday spirit is alive and well on the islands. Anguilla is less crowded, with many spots to dance the night away to the calypso beat. On St. Kitts and Nevis, the party begins on Boxing Day (the day after Christmas) and runs through the New Year. Meet the Rastafari, check out local dances and plays, and watch the joyful street parades.

Why charter in the Caribbean for the holiday season? Because the Caribbean is the only guaranteed warm weather yacht charter cruising location. Jump in the warm water without a wetsuit for a refreshing swim, with air temperatures averaging between 75 and 85 degrees Fahrenheit. There is an excellent selection of crewed private charter yachts from which to choose for your charter.

High-Season Holiday Tips for a Caribbean Yacht Charter

The holiday charter season does not necessarily mean big crowds! With so many Caribbean islands, all with their own distinct culture and flavor, it is easy to find peace and quiet. Whether you seek seclusion or want to enjoy a fun, festive environment with your family or guests, either is readily available in the Caribbean. Just let your charter broker know how you would like to spend the holiday season.

There are two charter locations in the Caribbean where New Year’s is celebrated with gusto! There has always been an annual New Year’s Eve party at Foxy’s on Jost Van Dyke Island in the British Virgin Islands where food, drinks, and dancing in the sand continue until the wee hours of the morning. Gustavia Harbour in St. Barths is a hopping scene with fireworks at midnight and a harbor filled with multimillion dollar charter and private yachts on anchor and stern at the main quay. There is an outdoor party on both sides of the quay, with dazzling parties taking place on various yachts, with ship’s tenders buzzing around the harbor. Parties ashore are happening at all of the night clubs.

Pricing for a Private Yacht Charter in the Caribbean

Caribbean, Children snorkeling on luxury yacht charter

Snorkeling in the Caribbean

As with other parts of the world, all private yacht charters in the Caribbean are booked through a yacht charter broker. They can explain pricing, which often scales in proportion to the size of the yacht. The larger the yacht, the higher the charter price.

Yacht charters are booked on a whole-boat basis. This means whether your group consists of 2 people or 12, the fee paid will be for the yacht charter itself and not per the number of occupied staterooms. Private yacht charter peaks at 12 guests per yacht as private yacht charter fits under international SOLAS rules and regulations that govern cruise ships and other multi-cabin ships that carry more than 12 guests, and can be booked “by cabin.”

Typically, there are two pricing structures when chartering a yacht found in the Caribbean:

  • All-inclusive—This pricing includes the yacht, crew, food, and beverages. Often there are other inclusions in the pricing as well. All inclusions and exclusions in the pricing should be clearly delineated by the charter broker. If there are any questions, you should feel free to ask. Yachts offered on an all-inclusive basis are usually sailing catamarans and some smaller sailing monohulls offered for crewed yacht charter in the British Virgin Islands, as the normal weekly expenses are well known in this cruising area.
  • Plus all expenses—This is the pricing structure more readily found in the Caribbean for most motor yachts and for many larger sailing yachts outside of the British Virgin Islands. With this pricing structure, you customize your trip, meaning you can ask for whatever you would like to have on board as far as food, beverage, and bar goes, and the itinerary is at your discretion. You are only charged for what you want, and your expenses are at the receipt price. The base charter price includes the yacht and crew, including the services of a chef, so food is charged at the grocery store receipt price. The cost of fuel, dockage, port fees, taxes, mooring ball fees and other additional charges depending on the charter location are also additional expenses charged based on that consumed, requested, or charged by authorities in the charter location.

For every charter, whether the pricing is all-inclusive or “plus all expenses,” it is customary at the end of the charter to leave a crew gratuity. This is discretionary and based on the quality of the service provided during the charter. A typical gratuity in the Caribbean is in the range of 10-20 percent of the charter fee for all-inclusive or the base charter fee for “plus all expenses.”

Caribbean Beach, Luxury Yacht Charter

Perfect Caribbean Beach

My advice? Get comfortable and ask questions. This way we can help to identify a yacht within the perfect price range for you and your guests. A Caribbean yacht charter vacation should be a relaxing and lovely experience, not one marred by financial worries, which your yacht charter broker can help to alleviate.

Now it’s time to begin asking questions about your own charter in the Caribbean this winter. Contact us and get started!