Looking for the best Caribbean yachts to charter this winter?
As winter approaches in the northern hemisphere, it’s the perfect time to start thinking ahead to your winter holidays. Leave the snow and cooler temperatures behind and escape to the white sand beaches and tropical sun of the Caribbean onboard your own luxury yacht.
With yachts quickly booking up, now is the time to make your plans and secure your yacht. We’ve curated a list of eight yachts that still have availability this winter in a wide range of sizes and budgets. Whether you’re a group of friends, a multigenerational family, or just a couple looking for some sun, this winter, The Superyacht People can help bring your dreams to fruition.
With the water at the perfect temperature, swathes of sandy beaches on offer and a multitude of island-hopping opportunities, the Caribbean was made for yacht charters. From the glamour of the Virgin Islands, to the glitz of St Barths, the quiet islands amongst the Grenadines, and crystal clear waters of the Bahamas, there’s an island and style for every type of charterer.
Regardless of which island or yacht you’d like to explore, your itinerary can be completely tailored to the style, tastes and desires of your group.
55M | USD 430,000 per week + expenses
Brand new in 2025 from Heesen Yachts, SOLEMATES has been designed around family, entertaining and relaxation. The 110-square-metre sundeck, Jacuzzi, beach club and onboard gym are major highlights for guests looking to make the most of their time onboard. For water sport enthusiasts, there is a wide selection of toys to choose from, including Jet Skis, Seabobs, an eFoil and sailing dinghy. Six spacious cabins are available for up to 12 guests looking to explore the Caribbean this winter.
49M | USD 295,000 per week + expenses
This contemporary, sustainability-minded charter yacht comes equipped with hybrid propulsion. A beautiful heated infinity pool, Jacuzzi, fold-down beach club and open-aiur cinema make this a great yacht for entertaining. Inside, light interiors lead to a full-beam master suite with a private balcony and accommodates 10 guests in five staterooms.
49M | USD 172,000 per week + expenses
Once owned by Malcom Forbes, this legendary Feadship has hosted a number of high profile and celebrity guests over the years.
46M | USD 180,000 per week + expenses
An excellent option for large or multigenerational groups, accommodating 12 guests in seven cabins. A large sundeck complete with Jacuzzi, outdoor cinema, gym and dedicated activity and media room is perfect for those looking for ample spaces to move about onboard. A great option for those searching for accessibility options, there is a lift that connects to all decks, while the extensive toy collection, inflatable water park and waterslide is great for families and active charterers.
32M | 120,000 per week + expenses
This modern 2024 Custom Line yacht is suited to smaller groups ins search of contemporary luxury. A beach club, main-deck master suite and stabilisers at anchor ensure a smooth and comfortable journey at every stop. A wide range of water toys including Jet Skis, Seabobs, fishing equipment and a large sportfishing tender. EVEXIAS I is perfect for groups of eight across five cabins including one convertible, three doubles, and one twin.
28M | 49,950 per week + expenses
Brand-new for 2026, MICHISAN brings Sanlorenzo’s refined Italian styling to the Caribbean. Accommodating eight guests across four cabins, she combines an intimate onboard atmosphere with a beach club, main-deck master suite and contemporary entertainment systems. Her cruising speed of 25 knots makes her particularly well suited to guests hoping to explore more of the islands, while a Jet Ski, eFoils, Seabobs and paddleboards provide plenty of fun once at anchor.
27M | 85,000 per week + expenses
Fresh from a 2026 refit, LOUDER is a relaxed and versatile option for families or groups of friends exploring the Caribbean. She accommodates eight guests in four double cabins and offers a beach club, main-deck master suite and stabilisers both underway and at anchor. Entertainment is a particular strength, with a karaoke machine, outdoor television, Jet Skis, an eFoil, underwater scooters and a 37-foot chase tender for adventures beyond the yacht.
23M | 60,000 per week + expenses
A spacious catamaran built for easy island-hopping, FRENCH WEST has space for eight guests in four cabins with a wide platform offering exceptional volume for her length. The owner’s suite includes a private beach platform with direct water access, while a family-friendly toy selection includes adult and children’s waterskis, wakeboards, sea scooters, paddleboards and a protected inflatable swimming area.
The right yacht depends on how you want to experience the Caribbean. SOLEMATES and ANJELIF offer contemporary superyacht luxury, with expansive outdoor spaces, impressive wellness amenities and exceptional access to the water. HIGHLANDER combines legendary Feadship heritage with the benefits of an extensive recent refit, while JUBILEE is particularly well suited to large and multigenerational groups.
EVEXIAS I balances modern comfort with fishing and adventures on the water, MICHISAN is ideal for faster-paced island-hopping, and LOUDER delivers relaxed, entertainment-led cruising. For generous living space and a laid-back catamaran experience, FRENCH WEST is an excellent choice.
Don’t see the right yacht for you? Explore all yachts available for charter now.
The Caribbean offers very different charter experiences from one island group to the next. You might picture afternoons at St Barths’ beach clubs, easy island-hopping through the Virgin Islands, or quieter days exploring the Grenadines. Each offers a different way to spend a week on the water, and the best choice depends on what your group wants from the trip.
Your destination also shapes which yachts make sense for your dates. Our team can help you compare the cruising grounds, find yachts available in the right area and plan an itinerary that brings it all together.
Start with our guide to the top Caribbean yacht charter destinations.
The Caribbean yacht season is quickly approaching and dates are filling up. If you’re looking to secure a yacht in the Caribbean this winter, especially around the holidays, please contact the team so we can help get the process started.
The Superyacht People will work with you throughout the process to create a fully curated itinerary and selection of yachts for you to choose from.
For Winter 2026-2027
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