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Where can I charter a superyacht in the Caribbean this Winter

By Nina Done   7 November 2022

Looking for inspiration for a winter yacht getaway? We’ve listed our top picks of the best destinations in the Caribbean for your next luxury yacht vacation.

With winter just around the corner, the tropical paradise of the Caribbean is the perfect getaway for those looking to escape the winter blues. And with a number of international airports serving the region, you can swap the cold weather for a sun-drenched beach at a moment’s notice. 

For some inspiration, we've compiled our top destination picks for the perfect luxury Caribbean yacht charter;

Leeward Islands

Forming a series of volcanic islands in the Caribbean’s West Indies, the Leeward archipelago comprises the perennially popular destinations of Antigua, Saint-Barthelemy, Saint Martin and Saint Kitts, and are renowned for their striking natural beauty and rich cultural heritage.

View over Antigua's English Harbor in the Caribbean

As the defining jewel in the Leeward Islands' crown, Antigua has enjoyed its status as a top yachting hub for centuries, home to idyllic beaches, gin-clear waters and favorable trade winds that have proven a heady combination for seafarers of all nationalities. 

Today, the island is a major hotspot for the SuperyachtSet and A-listers, who flock here every year to immerse themselves in the island’s unique colonial history, countless powder-fine beaches and 5-star resorts, including the celebrity favorite, Jumby Bay Spa.

Meanwhile, the exclusive island of Saint-Barthelemy, or St Barts, is the spot to head for New Year’s Eve, where some of the biggest and most luxurious superyachts in the world congregate to see in the new year, with the hottest parties in town taking place aboard these private floating palaces.

The chic capital of Gustavia also plays host to a wealth of luxury designer boutiques and world-class restaurants and cafes that spill onto the pavement, providing the perfect opportunity for a spot of celebrity spotting.

Nikki Beach in St Barts, Caribbean
Port de Gustavia in St Barts, CaribbeanHermes store front in St Barts

For something a little more idyllic, head to the French side of St Martin, offering a bevy of secluded palm-fringed beaches and beautiful anchorage spots. Saint Martin is also renowned as the gastronomic capital of the Caribbean, where you’ll find some of the finest cuisine to rival its Mediterranean cousins. 

Top things to do in the Leeward Islands;

  • Nelson’s Dockyard – A restored 18th Century dockyard in Antigua’s English Harbor, and the only remaining Georgian dockyard in the world.

  • Helicopter ride over Montserrat’s volcano – Offering the unique opportunity to witness the smoldering 3,000-feet Soufrière Hills volcano up close.

  • Dine & party at Eden Rock St Barts – The iconic Eden Rock is the ultimate place to see and be seen on your yacht charter.

  • Shop til’ you drop – Visit Gustavia’s harborside Quai de la République for high-end boutiques such as Louis Vuitton, Bvlgari and Cartier, to name but a few.

Windward Islands

Lush rainforests, idyllic beaches and tropical lagoons epitomize these islands in the heart of the Caribbean’s Windward Islands. Comprising 32 individual tropical landscapes, there is also an abundance of water sports activities for guests wishing to make the most of the beautiful turquoise waters. 

The twin pitons in St Lucia, Caribbean
Caribbean jungle with lush green exotic plants, beautiful tall palm trees on blue sky background

Known as the "Jewel of the Windward Islands", St Lucia is one of the most popular islands in the archipelago, famed for its towering twin Pitons that rise majestically from its lush forests awash with flora and fauna that act as a siren call to all superyachts visiting the iconic isle.  

Afterwards, be sure to make a beeline for the charming island of Bequia, one of the Caribbean’s best-kept secrets. Located 9 miles south of St Vincent, this untouched, sleepy outpost makes the ideal cruising spot for superyachts seeking a tranquil haven. Offering secluded beaches with fantastic snorkeling and diving opportunities, as well as a fine array of bars, restaurants and golf courses, this tiny isle presents the ultimate winter getaway on a luxury yacht charter.

St Lucia beach with huts and palm trees in the Caribbean
Golf course in the Caribbean at sunset
Snorkelers amid tropical fish in the Caribbean

St Vincent and its neighbouring Grenadines, meanwhile, offer a chilled, eco-friendly vibe, where intrepid charter guests can hike meandering forest trails and swim in dappled pools under cascading waterfalls. Harnessing the island’s natural resources, St Vincent also plays host to a raft of top eco-spas perfect for unwinding and relaxing.

Top things to do in the Windward Islands;

  • Hike the UNESCO World heritage-listed Pitons – Discover St Lucia’s famous dramatic twin peaks, surrounded by a marine park teeming with marine fauna.
  • Snorkel Bequia’s scenic lagoon – A protected cluster of 5 uninhabited islets surrounded by a glorious turquoise lagoon and coral reef, home to scores of green turtles and other tropical marine life.
  • Indulge yourself at the Treetop Spa – Nestled in amongst palm trees and lush greenery, the Treetop Spa in St Vincent is unquestionably one of the defining features of the picturesque Caribbean island.
  • Sulphur Springs and waterfall – Soak up the renowned health and detoxifying properties of St Lucia’s volcanic mud baths, made up of hot spring water and volcanic ash.

British Virgin Islands

Stretching for more than 30 miles, these emerald isles boast some of the most beautiful cruising grounds on the planet, peppered with pristine beaches, hidden coves and picturesque anchorages. Offering prime sailing yacht conditions, the region also plays host to some of the Caribbean’s best bars, marinas and spas, as well as numerous natural wonders.

A yacht anchored in the shallow turquoise waters of the BVIs

Roughly split between two island chains within close proximity to each other, separated by the Sir Francis Drake Channel, the British Virgin Islands are perfect for island hopping on a superyacht charter. The main island of Tortola on the northern side is the perfect place to kick off your winter getaway, offering up an eclectic mix of culture, lively bars and lush jungle, not to mention stretches of secluded sand beaches lapped by clear turquoise seas.

The Baths on Virgin Gorda in the BVIs, CaribbeanSnorkeler at the Baths on Virgin Gorda in the BVIs, Caribbean
British red telephone box in the BVIs, Caribbean

On the south side, you’ll find the popular hotspots Virgin Gorda and Norman Islands, both brimming with unspoilt beauty and alluring grottos. Meanwhile, party lovers should head for Jost Van Dyke, a diminutive isle that packs a punch, renowned for its hedonistic party vibe. There are also numerous restaurants and bars in which to enjoy a rum cocktail as the sun sets in a tangerine blaze, overlooked by the island's incredible verdurous mountain peaks. 

Top things to do in the British Virgin Islands;

  • The Baths in Virgin Gorda – BVI’s most famous landmark is a natural phenomenon of towering boulders that frame beautiful grottos and sea pools across a 7-acre national park, perfect for anchoring and snorkeling.
  • Foxy’s Bar – Set among palm trees on the party island of Jost Van Dyke, Foxy's is practically an institution offering a relaxed and friendly vibe, famous for its beach barbeques, signature cocktails and laid-back music scene.
  • Dive the wreck of RMS Rhone – Lying within a protected marine park between Salt Island and Dead Chest, this sunken British Royal Mail steamer is one of the top wreck dives in the Caribbean, where you’ll get the chance to spot a huge array of marine species, from Octopi to turtles, and much more.
  • Smuggler’s Cove – A hidden gem tucked away on the west coast of Tortola, offering a picture-perfect haven with blonde sands and impossibly blue waters perfect for snorkeling.
Caribbean beach at sunset with palm trees

To find out more about chartering in the region, please see our Caribbean yacht charter guide. For some inspiration, check out our sample itineraries handpicked by experts with in-depth knowledge of the region.

If you'd like to learn more about renting a luxury yacht, please get in touch with your chosen yacht charter broker

Alternatively, browse all of the superyachts available for charter in the Caribbean.

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