Windward Islands Charter Yachts and Sailing Vacations 2025-2026
Explore the wonderful Windward Islands from the unrivaled comfort of a luxury yacht charter 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 motor yacht, sailboat, or catamaran. We can also arrange luxury Eco-Friendly Charters in the windward islands.
See our Windward Islands Yacht Charter Guide
See Our Selection of the Finest Windward Island Charter Yachts for 2025-26 Below!
- Lagoon 52 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 Islands!"
- Fountaine Pajot Alegria 67 Crewed Catamaran
- Length: 20 m
- Year: 2022
- Cabins: 4
- Berths: 8
- From €40000 to €49000 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!"
- Sunreef 80 Luxury Crewed Catamaran
- Length: 23 m
- Year: 2024
- Cabins: 5
- Berths: 12
- From €93000 to €104000 per week
BOATBOOKINGS SAYS:
"Explore the British Virgin Islands and the plethora of scenic destinations aboard MISCHIEVOUS!"
- Lagoon Sixty 5 Luxury Crewed Catamaran
- Length: 20.42 m
- Year: 2023
- Cabins: 4
- Berths: 8
- From €50000 to €72000 per week
BOATBOOKINGS SAYS:
"Nightly rave parties await onboard REVE BLEU as you explore the South of France and the Caribbean!"
- Sunreef 80 Luxury Crewed Catamaran
- Length: 23.99 m
- Year: 2020
- 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!"
- 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: 2021
- Cabins: 3
- Berths: 6
- From $16500 to $20500 per week
BOATBOOKINGS SAYS:
"Get lulled by the gentle rhythmic waves of the Caribbean Windwards on RITMO!"
- 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 $22000 to $25000 per week
BOATBOOKINGS SAYS:
"Hurry up and book a remarkable cruise in the Caribbean on ANDIAMO!"
- Privilege Alliaura Marine Group 58 Crewed Motor Yacht
- Length: 17 m
- Year: 2004
- Cabins: 4
- Berths: 8
- From $23000 to $27000 per week
BOATBOOKINGS SAYS:
"LADY MARIGOT is your gateway to unforgettable adventures in the Caribbean year-round!"
- Lagoon 620 Crewed Catamaran
- Length: 18 m
- Year: 2018
- Cabins: 4
- Berths: 8
- From $28000 to $38000 per week
BOATBOOKINGS SAYS:
"ASCENSION will surely elevate your definition of luxurious cruising in the Caribbean!"
- CNB Bordeaux 21m Crewed Sailing Yacht
- Length: 21.36 m
- Year: 2018
- Cabins: 3
- Berths: 6
- From €17000 to €25300 per week
BOATBOOKINGS SAYS:
"You will realize that Sardinia has so much to offer and for you to see as you explore it onboard MAHINA 3!"
- Sunreef Supreme 68 Power Catamaran
- Length: 22 m
- Year: 2024
- Cabins: 4
- Berths: 8
- From $69000 to $75000 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: 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!"
- YYacht Y7 Crewed Sailing Yacht
- Length: 21.86 m
- Year: 2024
- Cabins: 3
- Berths: 6
- From €24000 to €28500 per week
BOATBOOKINGS SAYS:
"YUME, together with her outstanding crew, will surely amaze you and your group as you gasp with awe while witnessing the Balearics' highlights!"
- 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 $47300 to $54000 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 $90000 to $99000 per week
BOATBOOKINGS SAYS:
"Discover opulent living at sea on THE IDLER in Sardinia this summer!"
- Bali 4.8 Crewed Catamaran
- Length: 14.63 m
- Year: 2020
- Cabins: 3
- Berths: 6
- From $21000 to $25000 per week
BOATBOOKINGS SAYS:
"Experience a dreamy cruise on KITTIWAKE in the Bahamas!"
- Princess 82 Luxury Crewed Motor Yacht
- Length: 24 m
- Year: 2018 (2023 Refit)
- Cabins: 4
- Berths: 8
- From $35000 to $57600 per week
BOATBOOKINGS SAYS:
"You will surely be looked after by a passionate crew as you cruise the enchanting Caribbean islands on SORANA II."
- Numarine 26 XP Luxury Crewed Motor Yacht
- Length: 25 m
- Year: 2023
- Cabins: 4
- Berths: 8
- From $70000 to $75000 per week
BOATBOOKINGS SAYS:
"Dive into the alluring water of the Caribbean Leewards and make remarkable memories with your family on EXIT STRATEGY!"
- Sunseeker 95 Luxury Crewed Motor Yacht
- Length: 28 m
- Year: 2023
- 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: 43.89 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."
- 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 Luxury Crewed Catamaran
- Length: 14 m
- Year: 2022
- Cabins: 4
- Berths: 8
- From $19700 to $22700 per week
BOATBOOKINGS SAYS:
"Built in 2022 SERENITY, a brand new model catamaran, offers an abundance of space inside and out."
- Lagoon 50 Crewed Catamaran
- Length: 15 m
- Year: 2020
- Cabins: 4
- Berths: 8
- From $18000 to $35000 per week
BOATBOOKINGS SAYS:
"Step aboard the stunning luxury crewed catamaran KARMA and set sail around the beautiful British Virgin Islands!"
- 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!"
- 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 West Mediterranean and the Caribbean!"
- Robertson and Caine Leopard 50 Crewed Catamaran
- Length: 15.4 m
- Year: 2024
- Cabins: 3
- Berths: 6
- From $21000 to $25000 per week
BOATBOOKINGS SAYS:
"Lift your mood by embarking on a Caribbean cruise on BOATOX!"
