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 620 Crewed Catamaran
- Length: 18 m
- Year: 2019 (2022 Refit)
- Cabins: 4
- Berths: 8
- From $39500 to $42500 per week
BOATBOOKINGS SAYS:
"Feel the fresh Caribbean breeze aboard the DRAGONFLY on your British Virgin Islands cruise."
- Sunreef 80 Luxury Crewed Catamaran
- Length: 24 m
- Year: 2022
- Cabins: 4
- Berths: 8
- From $92000 to $100000 per week
BOATBOOKINGS SAYS:
"Enjoy unparalleled proportions, luxury, and comfort as you island-hop with Captain Jonathan and his vibrant crew on one of the finest Sunreef crewed catamarans in the Caribbean BVI and the Bahamas!"
- Benetti 121 Luxury Crewed Motor Yacht
- Length: 36.9 m
- Year: 2011 (2022 Refit)
- Cabins: 5
- Berths: 10
- From $110000 to $120000 per week
BOATBOOKINGS SAYS:
"Grace the shores of the Caribbean Leewards luxurious comfort on ALLORA!"
- Lagoon 620 Luxury Crewed Catamaran
- Length: 18 m
- Year: 2011 (2023 Refit)
- Cabins: 4
- Berths: 8
- From $35500 to $40500 per week
BOATBOOKINGS SAYS:
"A highly sought-after BVI crewed catamaran, perfect for families and friends alike."
- Sunseeker 95 Luxury Crewed Motor Yacht
- Length: 28 m
- Year: 2024
- Cabins: 5
- Berths: 10
- From $95000 to $115000 per week
BOATBOOKINGS SAYS:
"Experience exclusivity on ACCIDENTAL SUCCESS II while exploring the Caribbean Leewards your round!"
- Burger 144 Luxury Crewed Motor Yacht
- Length: 43 m
- Year: 2006 (2021 Refit)
- Cabins: 7
- Berths: 12
- From $175000 to $195000 per week
BOATBOOKINGS SAYS:
"CROSSED SABRE has the volume of a much larger motor yacht, ideal for charter in the Bahamas and the Caribbean."
- Moonen 122 Martinique Luxury Crewed Motor Yacht
- Length: 37.39 m
- Year: 2025
- Cabins: 5
- Berths: 10
- From $168000 to $182000 per week
BOATBOOKINGS SAYS:
"Where waves ignite, and stars delight, AD ASTRA cruises through the Bahamian and Caribbean nights!"
- Palmer Johnson 150 Luxury Crewed Motor Yacht
- Length: 45.7 m
- Year: 2009 (2024 Refit)
- Cabins: 5
- Berths: 10
- From $145000 to $160000 per week
BOATBOOKINGS SAYS:
"Be seen aboard the stylish NORMA JEAN, where Bahamas blues create a showstopping scene!"
- Bali 5.4 Crewed Catamaran
- Length: 16 m
- Year: 2019
- Cabins: 4
- Berths: 8
- From $28500 to $34000 per week
BOATBOOKINGS SAYS:
"She is a contemporary crewed catamaran, perfect for your next vacation in the British Virgin Islands with your nearest and dearest!"
- Benetti Motopanfilo 37m Luxury Crewed Motor Yacht
- Length: 36.91 m
- Year: 2022
- Cabins: 5
- Berths: 10
- From $160000 to $175000 per week
BOATBOOKINGS SAYS:
"KOJU was one of our standout yachts from FLIBS 2023; you will be dazzled by Captain Nick and his crew's dedication to delivering the ultimate Bahamas experience!"
- Fountaine Pajot Ipanema 58 Luxury Crewed Catamaran
- Length: 17 m
- Year: 2018 (2024 Refit)
- Cabins: 3
- Berths: 6
- From €25000 to €29000 per week
BOATBOOKINGS SAYS:
"You will surely enjoy your time soaking up the Sardinian and Caribbean sun while bathing in luxury on ARAOK!"
- Bali 4.8 Open Space Crewed Catamaran
- Length: 14 m
- Year: 2024
- Cabins: 4
- Berths: 8
- From $22500 to $28000 per week
BOATBOOKINGS SAYS:
"An extraordinary Caribbean journey awaits your family on BORROWED BOUNTY!"
- Dufour 48 Crewed Catamaran
- Length: 14 m
- Year: 2022
- Cabins: 4
- Berths: 8
- From $20000 to $24000 per week
BOATBOOKINGS SAYS:
"Built in 2022 SERENITY, a stunning catamaran model, offers an abundance of space inside and out."
- Lagoon Seventy 7 Luxury Crewed Catamaran
- Length: 23.28 m
- Year: 2021 (2024 Refit)
- Cabins: 4
- Berths: 8
- From €77000 per week
BOATBOOKINGS SAYS:
"Experience the serenity of nature amidst the Caribbean Leewards aboard the luxurious catamaran CAT TUA!"
- Bilgin 163 I Luxury Crewed Motor Yacht
- Length: 49.95 m
- Year: 2024
- Cabins: 6
- Berths: 12
- From €334800 to €349800 per week
BOATBOOKINGS SAYS:
"ETERNAL SPARK is a new Bilgin yacht that redefines luxurious cruising in the French Riviera!"
- Lagoon 52 Crewed Catamaran
- Length: 15 m
- Year: 2019
- Cabins: 6
- Berths: 12
- From €9750 to €15600 per week
BOATBOOKINGS SAYS:
"DUGONGO II is an intimate crewed catamaran ideal for a family charter in the Caribbean!"
- Robertson and Caine Leopard 50 Crewed Catamaran
- Length: 15.4 m
- Year: 2024
- Cabins: 3
- Berths: 6
- From $21000 to $26000 per week
BOATBOOKINGS SAYS:
"Lift your mood by embarking on a Caribbean cruise on BOATOX!"
- Fountaine Pajot Sanya 57 Luxury Crewed Catamaran
- Length: 17 m
- Year: 2012 (Yearly Refit)
- Cabins: 4
- Berths: 8
- From $31000 to $35000 per week
BOATBOOKINGS SAYS:
"Sign up for an extraordinary cruising vacation in the Caribbean on ODYSSEA, a sleek and luxurious catamaran built for your adventures!"
- Moon Yacht 6TY Luxury Crewed Catamaran
- Length: 19 m
- Year: 2023
- Cabins: 5
- Berths: 10
- From $50000 to $58000 per week
BOATBOOKINGS SAYS:
"Smooth as a breeze, MOON SHADOW will take you to exclusive breathtaking anchorages across the Caribbean!"
- Fountaine Pajot Alegria 67 Luxury Crewed Catamaran
- Length: 20 m
- Year: 2023
- Cabins: 4
- Berths: 8
- From $50000 to $63000 per week
BOATBOOKINGS SAYS:
"JEWEL is a real gem amidst the Caribbean Island treasures!"
- Vicem 46 Vulcan Luxury Crewed Motor Yacht
- Length: 46.02 m
- Year: 2013 (2021 Refit)
- Cabins: 6
- Berths: 12
- From €180000 to €220000 per week
BOATBOOKINGS SAYS:
"Let HATT MILL take the wheel, where Corsica’s cliffs and turquoise waters feel surreal!"
- Fountaine Pajot Astrea 42 Crewed Catamaran
- Length: 12 m
- Year: 2020
- Cabins: 2
- Berths: 4
- From $15750 to $17000 per week
BOATBOOKINGS SAYS:
"Spice up your Caribbean Windwards cruise on the Fountaine Pajot Astrea 42 RISE!"
- Leopard 45 Crewed Catamaran
- Length: 13 m
- Year: 2020
- Cabins: 3
- Berths: 6
- From $19500 to $21500 per week
BOATBOOKINGS SAYS:
"Get ready to shake to the Caribbean groove on SEA DANCER!"
- Robertson and Caine 42 Crewed Catamaran
- Length: 13 m
- Year: 2011
- Cabins: 4
- Berths: 7
- From $13950 to $17150 per week
BOATBOOKINGS SAYS:
"Dance or get lulled into a trance on GROOVY with her excellent crew, who will give you a fantastic charter experience from the Windwards to Leewards!"
- Robertson and Caine 43 Crewed Catamaran
- Length: 13 m
- Year: 2000 (2023 Refit)
- Cabins: 3
- Berths: 6
- From $12500 to $15500 per week
BOATBOOKINGS SAYS:
"Feel your worries drop away as NOVA paints the Caribbean in shades of play!"
- Leopard 46 Crewed Catamaran
- Length: 14 m
- Year: 2012 (2023 Refit)
- Cabins: 3
- Berths: 7
- From $12000 to $17900 per week
BOATBOOKINGS SAYS:
"Your camera will never rest from the spectacular scenery of the Caribbean on SARA!"
- Bali 4.8 Luxury Crewed Catamaran
- Length: 14 m
- Year: 2022
- Cabins: 3
- Berths: 6
- From $15000 per week
BOATBOOKINGS SAYS:
"For sunshine that is sweeter and blue water that is cleaner, chart your escape aboard MY MARINA through the Caribbean Windwards."
- Lagoon 46 Luxury Crewed Catamaran
- Length: 14 m
- Year: 2020
- Cabins: 4
- Berths: 10
- From €8394 to €10387 per week
BOATBOOKINGS SAYS:
"The enormous flybridge will have your whole family immersed in the art of sailing on your Caribbean charter aboard WESTERLUND!"
- Bali 4.6 Luxury Crewed Catamaran
- Length: 14 m
- Year: 2024
- Cabins: 5
- Berths: 10
- From $24500 to $28500 per week
BOATBOOKINGS SAYS:
"In the Leeward Islands, LOBA DO MAR sets the bar, carrying you through waters that sparkle like a guiding star!"
- Fountaine Pajot Aura 51 Crewed Catamaran
- Length: 15 m
- Year: 2022
- Cabins: 4
- Berths: 6
- From $21900 to $28680 per week
BOATBOOKINGS SAYS:
"A rare and unique opportunity to charter a new Fountaine Pajot Aura 51 in the Leewards and Grenadines in the Winter, and the Bahamas in the Summer."
