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Winter yacht charters: Our top picks for Caribbean, Indian Ocean and beyond
Published 13 十月 2025
Whether it’s the cool trade winds in the Caribbean, the tropical bounty islands of the Maldives or the calm, shallow waters of the Seychelles, crewed yacht charters in warmer climes are a blissful way to escape grey skies in the winter months.
From barefoot island-hopping to diving coral reefs and dining under the stars, discover our top picks for the best winter holiday destinations to explore by yacht.
Why choose a winter yacht charter?
Swap the boardroom suit for a wetsuit before diving headfirst from the aft deck into clear turquoise waters. Anchoring off a white-sand island in a secluded bay aboard your private yacht is the perfect way to while away long, sun-soaked days in complete privacy.
With freedom, safety and comfort seamlessly combined, life aboard a private superyacht is effortless – and endlessly rewarding.
Escape the cold in style
Feeling the sun on your skin in midwinter is a salve for the soul. Instead of snow boots, walk barefoot along the deck of your yacht or sink your toes into powder-soft sand while visiting islands throughout the Caribbean, the Maldives or Costa Rica. Begin your mornings with a refreshing swim in crystal-clear waters, then head ashore for island adventures or spend the day playing with the yacht’s watertoys.
From paddleboarding over coral gardens to sunset dining on deck, every moment is designed for relaxation and renewal.
More availability and flexibility in off-season
A winter yacht charter offers greater flexibility than peak-season cruising. With fewer crowds, you’ll enjoy your pick of sought-after anchorages, hidden coves and waterfront restaurants.
Whether you’re seeking a week-long getaway or a longer voyage, winter charters allow you to choose dates, destinations and itineraries that fit your pace. Every element of your itinerary can be fully customised to suit your preferences – from high-octane adventure to total serenity.
Where can I charter this winter?
The Caribbean and Bahamas remain the most popular winter yacht charter destinations thanks to their warm climates and easy access from the USA. These regions offer a secluded paradise of untouched beaches, colourful marine life and countless uninhabited islands to explore.
For those seeking something a little different, Costa Rica delivers wild natural beauty and adventure, while the Seychelles and Maldives offer idyllic cruising grounds in the Indian Ocean, with some of the world’s best diving.
Caribbean for island hopping and barefoot luxury
The Caribbean islands are made for yacht exploration, each offering a distinct rhythm and charm. From the French flair of Martinique to the volcanic peaks of St Lucia, and from the Grenadines’ unspoiled bays to the lush rainforests of Tobago, every island reveals something new. Hike through rainforest trails to hidden waterfalls, enjoy beach barbecues on deserted cays, or snorkel among coral gardens teeming with parrotfish and sea turtles.
Whichever route you take, a Caribbean yacht charter offers the ultimate in barefoot luxury – where days drift between sailing, swimming and soaking up the sun.
Bahamas for shallow waters and endless beaches
With more than 700 islands and cays, The Bahamas promise limitless cruising opportunities. The Exumas are a favourite for their translucent shallows and unique experiences – swim through the Thunderball Grotto cave made famous by James Bond, feed gentle nurse sharks, and visit the iconic swimming pigs of Big Major Cay.
Farther north, Harbour Island near Eleuthera offers pink-sand beaches, chic boutiques and relaxed island glamour. Thanks to their shallow draft, many yachts can anchor close to shore, giving guests direct access to the turquoise shallows that make a yacht rental in Nassau or the Exumas so magical.
Maldives for private escapes and warm seas
A chain of over 1,000 coral islands, the Maldives is the definition of paradise. While many islands host luxury resorts, a Maldives yacht rental offers the ultimate freedom – the chance to wake up to a new horizon each day. Drop anchor off an uninhabited atoll, snorkel with manta rays, or enjoy a private sandbank picnic at sunset.
With consistently warm seas and gentle breezes, the Maldives are ideal for winter sailing. Dive among vibrant reefs, fish for tuna with the crew, or simply unwind on deck surrounded by nothing but turquoise and tranquillity.
Seychelles for luxury diving opportunities
Floating in the Indian Ocean off East Africa, the Seychelles’ 115 islands are a natural playground of granitic peaks, palm-fringed beaches and coral lagoons. The Inner Islands, including Mahé, Praslin and La Digue, offer world-class anchorages and short cruising distances between them. The Outer Islands are even more remote, known for pristine coral reefs and exceptional diving.
Aboard your Seychelles yacht charter, explore UNESCO-listed Vallée de Mai, dive among whale sharks or stroll across powder-white sands at Anse Source d’Argent. With its rich biodiversity and serene anchorages, the Seychelles are perfect for those seeking nature, privacy and luxury in equal measure.
Costa Rica for new adventures
Translating literally to the ‘rich coast’, Costa Rica is one of the world’s most biodiverse nations and a rising destination for yacht charters. The country’s Pacific coastline offers lush rainforests, dramatic volcanoes and wildlife-filled national parks – all best explored by sea.
Cruise the Nicoya Peninsula, where secluded bays and surf breaks await, or head to the Osa Peninsula for encounters with dolphins, sea turtles and even migrating humpback whales. On land, zipline through rainforest canopies or explore local eco-lodges that showcase the country’s commitment to sustainability.
A Costa Rica yacht charter combines exploration and conservation – adventure with meaning.
What to look for in a superyacht for a winter charter
Whether you’re lounging on a sprawling beach club or sailing between atolls, the right yacht makes all the difference. Choose a yacht with an experienced crew who know the best anchorages, a shallow draft for exploring close to shore, and a well-equipped tender for island-hopping. Watertoys such as SeaBobs, paddleboards and diving gear elevate every moment on the water, while shaded deck spaces and on board spas ensure complete comfort between adventures.
Which yachts are available to charter this winter with Burgess?
From family-friendly explorer yachts to sleek motor yachts with open-air beach clubs, Burgess offers a diverse fleet ready for winter charters across the Caribbean, Bahamas, Indian Ocean and beyond.
Our expert brokers will match you with the perfect yacht and crew, curating every detail of your itinerary – from daily menus to hidden anchorages – so that your experience is seamless from start to finish. Explore our current listings and find your dream winter yacht charte today.
Ready to plan your winter charter?
Whether you're dreaming of a Caribbean escape, a Bahamian beach adventure or a Maldivian island odyssey, Burgess will bring your perfect winter charter to life.
Enquire today for rates, dates and sample itineraries with the Burgess team and set sail for a season of sunshine.
To find out more about Burgess’ yachts for sale and yachts for charter, please contact a Burgess broker. Alternatively, get in touch with one of our offices directly: London, Monaco, New York, Miami, Singapore or all other locations.
– Yachts, prices and availability are correct at the time of publication.
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