The Burgess guide to the 2026 sailing regatta calendar
Winter yacht charters in the Caribbean
Published 19 一月 2026
A Caribbean winter yacht charter is an escape that promises crystal-clear waters, sun-soaked beaches, and unforgettable experiences. Whether you're a seasoned yacht charterer or exploring the idea for the first time, this guide covers everything you need to know about planning a Caribbean yacht charter. From the best destinations and activities to expert recommendations, we’ll ensure you make the most of your luxurious winter yacht rental in this tropical paradise.
Why the Caribbean is perfect for a winter yacht charter holiday
The appeal of a winter yacht charter in the Caribbean is undeniable. While the Mediterranean cools down after a busy summer season, the Caribbean remains a blissful escape for some winter sun.
With over 7,000 islands and cays to discover, a Caribbean yacht charter offers diverse landscapes, rich cultures, and endless opportunities for adventure. Whether you prefer lively beach towns or serene hideaways, the Caribbean's crystal-clear waters and steady winds make it the perfect destination for both motor yachts and sailing yachts.
When is the best time to charter in the Caribbean?
The best time to charter a yacht in the Caribbean is from November to April, when the region enjoys its high season. During these months, the climate is warm and sunny, with gentle Caribbean trade winds creating ideal conditions for sailing and cruising.
For those looking for quieter periods, May to June offers warm weather and fewer tourists, though hurricane season officially begins in June. The peak of hurricane season is from August to October, and while yachting is still possible, it’s essential to monitor weather conditions closely and plan in advance – something that Burgess’ charter brokers do for all clients.
Where to charter in the Caribbean this winter
The Caribbean is a collection of diverse islands, each offering unique attractions and experiences. Choosing the right islands can make or break your charter, but our expert team are on hand to discuss your requirements – are you looking for a slower pace and deserted beaches or somewhere for adventure? – and will create the perfect Caribbean itinerary for you and your guests.
To get you started on your journey, here's a look at some of the top island groups to visit on your Caribbean yacht rental.
Relaxed island hopping and sailing
British Virgin Islands
Known for their stunning beauty and serene atmosphere, the British Virgin Islands is one of the most popular choices for yacht charters. The BVI offers smooth sailing conditions, protected anchorages, and picture-perfect beaches like those at Virgin Gorda or Anegada. Popular spots include The Baths, a geological wonder, and the famous Soggy Dollar Bar on Jost Van Dyke. For more, including our picks of the best beaches in the Virgin Islands, explore in detail here.
Winter sunshine and shallow cruising grounds
The Bahamas
A Bahamas yacht charter offers over 700 islands and cays, from the bustling Nassau to the secluded Exumas. With turquoise waters, world-class diving spots like the Blue Hole, and endless stretches of white sandy beaches, a superyacht charter in The Bahamas is popular for good reason. Opt for a yacht with a shallow draft, such as ROYALE X, as these are uniquely suited to the shallow waters and island hopping itineraries that The Bahamas positively encourage
Culture and beaches
Leeward Islands
For those looking for a perfect blend of history, culture and breathtaking scenery, a Leeward Islands yacht charter should be the top of your list. Most notable among these islands are Antigua and St Kitts and Nevis. Antigua alone boasts 365 beaches – one for each day of the year – and its bustling harbours are home to the famous Antigua Sailing Week. For a slower pace, head to Nevis with its relaxed atmosphere, volcanic landscapes and luxurious hideaways.
Longer charter itineraries, adventure, and scenery
Windward Islands
The Windward Islands include Grenada, St Lucia, and St Vincent and the Grenadines. Known for their lush rainforests, mountainous landscapes, and vibrant coral reefs, these islands are the perfect addition to an adventurous Caribbean itinerary. For dramatic views, St Lucia’s Pitons are the two iconic twin peaks that offer incredible hikes (challenging, but the views are well worth it!), while Grenada is famous for its spice plantations and underwater sculpture park.
Easy access and diverse cruising opportunities
US Virgin Islands
Neighbouring the British Virgin Islands, a US Virgin Islands yacht charter offers a slightly different flavour. With a mix of natural beauty and rich history, you can explore sites like Trunk Bay or St John, one of the most photographed beaches in the world, or enjoy the lively energy of St Thomas. Uncover the best of the USVIs here, and how Burgess can create an island hopping itinerary around both the US and British Virgin Islands for an authentic taste of island life.
Best superyachts for a Caribbean winter charter
When it comes to private yacht charters, Burgess has an impressive fleet of motor and sailing yachts available in the Caribbean. Here are some top picks for your next charter. Whether you're looking for a motor or sailing yacht, something with endless watertoys, or something with a shallow draft that will see you anchoring close to remote islands, there's something in the Burgess charter fleet that's perfect for you.
Burgess motor yachts
For those seeking luxury and comfort, a motor yacht is the ideal choice. These vessels come equipped with lavish amenities, expansive decks, state-of-the-art entertainment systems, and a professional crew who ensure a five-star experience.
Burgess sailing yachts
If you're after the authentic charm of wind-powered sailing, Burgess offers an exclusive collection of sailing yachts. These yachts provide the perfect combination of elegance and adventure, giving you the opportunity to explore the Caribbean in style while harnessing the natural elements.
Seven-day Caribbean yacht charter itinerary
A Caribbean yacht charter is as much about the journey as it is about the destinations. To truly savour the region’s sun-soaked islands, turquoise waters, and vibrant culture, we recommend a minimum of seven days. This gives you the time to relax, explore, and immerse yourself in the unique experiences each island has to offer.
From hidden beaches to thrilling water activities, here are a few must-do highlights that will make your winter yacht charter unforgettable.
Island hopping and private anchorages
With so many islands and so much choice, it can be hard to know where to start. We'd suggest commencing your island hopping journey in one of the key gateway islands – Barbados, Antigua, or St Lucia – and from there setting course to the less developed islands to unlock a world of untapped beauty for a truly memorable adventure.
We'd argue that island hopping is the best way to see the region at its most authentic, as you'll cruise between lively islands and more laid-back ones, experiencing the Caribbean atmosphere at its fullest.
Snorkelling, diving, and watersports charters
The Caribbean is home to some of the best snorkelling and diving spots in the world, and winter diving conditions are excellent. From exploring vibrant coral reefs to swimming with sea turtles, manta rays, and even dolphins, the underwater world here is magical. Dive the wreck of the RMS Rhone in the BVIs or explore the Thunderball Grotto in The Bahamas for a truly immersive experience.
For the adventurous, a Caribbean yacht charter offers plenty of opportunities for watersports (think jetskiing, paddleboarding, and deep-sea fishing). Thanks to calm and warm waters, it's the perfect playground for water lovers of all skill levels.
Ready to set sail for the Caribbean?
The Caribbean is a yachting playground like no other, offering a mix of nature, adventure, and relaxation. Whether you’re dreaming of a BVI yacht charter or exploring the wonders of Antigua, Burgess offers world-class services to ensure your Caribbean yacht charter is an unforgettable experience. Ready to embark on your tropical escape? Contact Burgess today to start planning the ultimate Caribbean getaway.
Speak to our Burgess Charter team, and let us plan your perfect yacht vacation.
Frequently asked questions
Do I need to book a Caribbean winter yacht charter far in advance?
In short: yes. The Caribbean winter season is peak yachting time, running roughly from December through April, so yachts book up quickly. Planning several months ahead ensures you have the widest choice of yachts, itineraries, and preferred dates. Booking early also gives you the chance to secure any special requests, such as a particular crew, watertoys, or unique experiences, making your charter truly seamless.
We do, however, have several yachts with last minute availability in the Caribbean. So if you decide spur of the moment to escape somewhere sunny, speak to our charter brokers who can discuss your options.
What experiences can you enjoy on a Caribbean winter yacht charter?
A Caribbean winter yacht charter offers more than just sun and sea. You can explore hidden coves, pristine beaches, and vibrant local culture across islands like St Barths, the British Virgin Islands, or the Grenadines. On board, enjoy tailor-made activities like diving, snorkelling, paddleboarding, or deep-sea fishing. Some yachts even offer spa treatments, gourmet dining prepared by private chefs, and immersive experiences with local communities or wildlife. Every day can be a blend of adventure, relaxation, and luxury at your pace.
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.
Latest stories
The Burgess guide to the 2026 sailing regatta calendar
First launch of 2026: Benetti Class 44
New to the charter fleet
Miami International Boat Show
St Barths Bucket Regatta
