Windward Islands Charter Yachts and Sailing Vacations 2025-2026
Explore the wonderful Windward Islands in 2026 and 2027 from the unrivaled comfort of a luxury motor yacht charter or crewed catamaran and discover an unmatched kind of relaxation!
The Windward Islands are a historical sailing ground named by sailors coming to the America's on trans-Atlantic currents and winds. As these sailing ships arrived in the New World they named the islands the windwards because of their rougher conditions as compared to the more southernly protected Leeward Islands. Renowned for sailing vacations and yacht charters, the Windward Islands offer all the best features of the Caribbean- sun, beach, marine life, beautiful water, and of course, great island-to-island sailing!
The main islands are: Martinique, Saint Lucia, Saint Vincent and the Grenadines, Grenada, Dominica, Trinidad and Tobago, and Barbados. Our Boatbookings Charter Experts can find the perfect charter yacht for your Windward islands vacation whether you are looking for a Caribbean motor yacht, sailboat, or crewed catamaran. We can also arrange luxury Eco-Friendly Charters in the Windward islands.
See our Windward Islands Yacht Charter Guide 2026 and 2027
See Our Selection of the Finest Windward Island Charter Yachts for 2026 and 2027 Below!
- Lagoon 52 Luxury Crewed Catamaran
- Length: 15 m
- Year: 2022
- Cabins: 4
- Berths: 8
- From $31000 to $40000 per week
BOATBOOKINGS SAYS:
"LIQUID ZEN is a luxurious den amidst the beautiful Caribbean Virgin Islands!"
- Lagoon Seventy 7 Luxury Crewed Catamaran
- Length: 23 m
- Year: 2019
- Cabins: 4
- Berths: 8
- From $74000 to $80000 per week
BOATBOOKINGS SAYS:
"Spend a week on the Caribbean's most sought-after crewed catamaran!"
- Fountaine Pajot Alegria 67 Crewed Catamaran
- Length: 20 m
- Year: 2023
- Cabins: 4
- Berths: 8
- From $48000 to $54000 per week
BOATBOOKINGS SAYS:
"Live your daydream aboard LOOMA, the brand new catamaran that promises an unforgettable adventure exploring the highlights of Sardinia!"
- Lagoon 620 Crewed Catamaran
- Length: 18 m
- Year: 2021
- Cabins: 4
- Berths: 8
- From $39000 to $42000 per week
BOATBOOKINGS SAYS:
"ASTROLABE is a luxurious and spacious choice for sailing the West Mediterranean and the Caribbean, and you won't be disappointed!"
- Mangusta Oceano 50 Luxury Crewed Motor Yacht
- Length: 49.99 m
- Year: 2022
- Cabins: 6
- Berths: 12
- From $295000 to $320000 per week
BOATBOOKINGS SAYS:
"Sleek and luxurious, embrace the suave as you venture through the Caribbean wonders on MAVERICK!"
- Sunreef 80 Luxury Crewed Catamaran
- Length: 23 m
- Year: 2024
- Cabins: 5
- Berths: 12
- From €96000 to €120000 per week
BOATBOOKINGS SAYS:
"Explore the British Virgin Islands and the plethora of scenic destinations aboard MISCHIEVOUS!"
- Lagoon Seventy 7 Luxury Crewed Catamaran
- Length: 23 m
- Year: 2022
- Cabins: 4
- Berths: 8
- From €60000 to €69000 per week
BOATBOOKINGS SAYS:
"Discover the enchanting tropical beauty of the Caribbean aboard KAJIKIA, a true marvel by Lagoon!"
- Lagoon Sixty 5 Luxury Crewed Catamaran
- Length: 20.55 m
- Year: 2023
- Cabins: 4
- Berths: 8
- From €45000 to €50000 per week
BOATBOOKINGS SAYS:
"Explore calm coves and isles anew as REVE BLEU glides through the Caribbean and the West Mediterranean’s hue!"
- Sunreef 80 Luxury Crewed Catamaran
- Length: 23.99 m
- Year: 2020 (2023 Refit)
- Cabins: 4
- Berths: 8
- From $60000 to $80000 per week
BOATBOOKINGS SAYS:
"SEACLUSION is one of the top catamarans chartering the Caribbean and has won the Best Yacht in the 2022 USVI Yacht Show!"
- Fountaine Pajot Alegria 67 Luxury Crewed Catamaran
- Length: 20 m
- Year: 2022
- Cabins: 4
- Berths: 8
- From €56000 to €60000 per week
BOATBOOKINGS SAYS:
"SEMPER FIDELIS is always faithful to her mission of providing top-notch hospitality while exploring the Caribbean and the Bahamas."
- Sunreef 60 Luxury Crewed Catamaran
- Length: 18.3 m
- Year: 2025
- Cabins: 4
- Berths: 8
- From $46000 to $52000 per week
BOATBOOKINGS SAYS:
"Shout Booyah for OYA and let the Caribbean Islands turn your cruising adventure up a notch!"
- Fountaine Pajot Alegria 67 Luxury Crewed Catamaran
- Length: 19.49 m
- Year: 2024
- Cabins: 4
- Berths: 10
- From $35000 to $45000 per week
BOATBOOKINGS SAYS:
"Get ready to say WOW upon witnessing the enchanting and stunning visual prowess of the Caribbean aboard NEOW!"
- Lagoon Seventy 7 Luxury Crewed Catamaran
- Length: 23.84 m
- Year: 2025
- Cabins: 4
- Berths: 8
- From €60000 to €82800 per week
BOATBOOKINGS SAYS:
"Follow the sun across Sardinia aboard REVA NUI, where polished cruising and postcard-perfect anchorages come together beautifully."
- Lagoon 55 Luxury Crewed Catamaran
- Length: 16 m
- Year: 2023
- Cabins: 5
- Berths: 10
- From $35000 to $42000 per week
BOATBOOKINGS SAYS:
"Don't settle for less and experience more in your BVI cruise on VALINOR - Winter!"
- Privilege Alliaura Marine Group 58 Luxury Crewed Catamaran
- Length: 17 m
- Year: 2004
- Cabins: 4
- Berths: 8
- From $25500 to $29500 per week
BOATBOOKINGS SAYS:
"LADY MARIGOT is your gateway to unforgettable adventures in the Caribbean year-round!"
- Sunreef Supreme 68 Power Catamaran
- Length: 20 m
- Year: 2024
- Cabins: 4
- Berths: 8
- From $63500 to $69500 per week
BOATBOOKINGS SAYS:
"Indulge in an everyday feast while cruising the BVI on MARIA THERESE!"
- Lagoon 620 Luxury Crewed Catamaran
- Length: 18.89 m
- Year: 2017
- Cabins: 3
- Berths: 6
- From $42000 to $46000 per week
BOATBOOKINGS SAYS:
"LE REVE is the leading 3 cabin crewed catamaran in the BVI or in New England with an amazing crew, really amazing crew. You will not be disappointed!"
- Lagoon 46 Crewed Catamaran
- Length: 14 m
- Year: 2020
- Cabins: 3
- Berths: 6
- From $16500 to $18500 per week
BOATBOOKINGS SAYS:
"Party all night and dance tango with your loved ones on the Lagoon 46 MONDANGO!"
- Leopard 50 Crewed Catamaran
- Length: 15.24 m
- Year: 2023
- Cabins: 3
- Berths: 6
- From $27500 to $30000 per week
BOATBOOKINGS SAYS:
"Hurry up and book a remarkable cruise in the Caribbean on ANDIAMO!"
- Lagoon 620 Crewed Catamaran
- Length: 18 m
- Year: 2018
- Cabins: 4
- Berths: 8
- From $38000 to $44000 per week
BOATBOOKINGS SAYS:
"ASCENSION will surely elevate your definition of luxurious cruising in the Caribbean!"
- Lagoon 620 Luxury Crewed Catamaran
- Length: 18.89 m
- Year: 2016 (2017 Refit)
- Cabins: 4
- Berths: 8
- From $33000 to $37000 per week
BOATBOOKINGS SAYS:
"ECLIPSE is the perfect way to explore the British Virgin Islands with friends and family this season!"
- Trinity 161 Luxury Crewed Motor Yacht
- Length: 49 m
- Year: 2007 (2024 Refit)
- Cabins: 5
- Berths: 12
- From €225000 per week
BOATBOOKINGS SAYS:
"Find more than what you came for aboard DIRT POOR, where Bahamian blues make every moment feel rich to the core!"
- Fountaine Pajot Alegria 67 Luxury Crewed Catamaran
- Length: 20 m
- Year: 2025
- Cabins: 4
- Berths: 8
- From $58000 to $61000 per week
BOATBOOKINGS SAYS:
"Get ready for the newest Fountaine Pajot 67 in the BVI and be the first to charter SAPPHIRE!"
- Fountaine Pajot Alegria 67 Crewed Catamaran
- Length: 20 m
- Year: 2021
- Cabins: 4
- Berths: 8
- From €45000 to €50000 per week
BOATBOOKINGS SAYS:
"Be inspired by the Jacuzzi and enchanting vistas of Croatia or the Caribbean on INSPIRANTE!"
- Christensen 162 Luxury Crewed Motor Yacht
- Length: 49.37 m
- Year: 2011 (refit 2020)
- Cabins: 6
- Berths: 8
- From $230000 to $230000 per week
BOATBOOKINGS SAYS:
"Step onboard REMEMBER WHEN and enjoy the Bahamas and Caribbean in unrivalled luxury this year."
- Fountaine Pajot Ipanema 58 Crewed Catamaran
- Length: 18.28 m
- Year: 2018
- Cabins: 5
- Berths: 8
- From $34200 to $39900 per week
BOATBOOKINGS SAYS:
"Outstanding is the word for this crewed catamaran - just have a look at the reviews from clients!"
- Matrix Silhouette 76 Luxury Crewed Catamaran
- Length: 22.34 m
- Year: 2006 (2017 Refit)
- Cabins: 5
- Berths: 10
- From $49800 to $57500 per week
BOATBOOKINGS SAYS:
"Zingara never ceases to please those looking for quality sailing and deluxe comfort!"
- Sunreef Eco 80 Luxury Crewed Catamaran
- Length: 24 m
- Year: 2024
- Cabins: 4
- Berths: 8
- From $95000 to $99000 per week
BOATBOOKINGS SAYS:
"Sail between worlds of beauty aboard THE IDLER, basking in Sardinia’s golden summer and Caribbean bliss when winter arrives!"
- Oyster 885 Luxury Crewed Sailing Yacht
- Length: 27 m
- Year: 2025
- Cabins: 4
- Berths: 8
- From $65000 per week
BOATBOOKINGS SAYS:
"Under skies so blue and waters aglow, Antigua comes alive when you’re on SUNYO!"
- Bali 5.4 Crewed Catamaran
- Length: 16 m
- Year: 2024
- Cabins: 4
- Berths: 8
- From $31000 to $35000 per week
BOATBOOKINGS SAYS:
"Take in the lovely vistas of the British Virgin Islands on award-winning catamaran LA VIE EST BELLE!"
