Windward Islands Charter Yachts and Sailing Vacations
The Windward Islands are so named because they were more windward to sailing ships arriving in the New World than the Leeward Islands, given that the prevailing trade winds in the West Indies blow east to west.
The Windward Islands are renowned for sailing vacations and yacht charters because they offer all the best of that which is Caribbean - sun, beach, marine life, beautiful water, and of course, great island to island sailing! The main islands in the Windwards are: Martinique, Saint Lucia, Saint Vincent and the Grenadines, Grenada, Dominica, Trinidad and Tobago and Barbados.
We can find you the perfect charter yacht in the Windward Islands, and recommend itineraries that suit your needs. Just check through the boats below or simply contact us and we will recommend the perfect boat for you!
If you’re interested in an Ecological Charter, see our Grenada Eco Tourism Guide.
Sort through the charter yachts below or use these handy links to quickly find the yachts that best fit your needs:
Motor Yachts: Crewed
Monohull Sailing Yachts: Bareboat (inc. Bareboat with Skipper) | Crewed
Catamarans: Bareboat (inc. Bareboat with Skipper) | Crewed
Yachts for Special Events: Motor Yachts
- Fountaine Pajot Alegria 67 Crewed Catamaran
- Length: 20 m
- Year: 2022
- Cabins: 4
- Berths: 8
- From €34000 to €40000 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!"
- 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!"
- Fountaine Pajot Alegria 67 Crewed Catamaran
- Length: 20.42 m
- Year: 2024
- Cabins: 4
- Berths: 8
- From $48000 to $54000 per week
BOATBOOKINGS SAYS:
"LIQUID SKY always offers an exceptional aquatic adventure in the Caribbean Virgin Islands."
- 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!"
- 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 the Caribbean this summer!"
- 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!"
- 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."
- Fountaine Pajot Ipanema 58 Luxury Crewed Catamaran
- Length: 17.8 m
- Year: 2018 (2022 Refit)
- Cabins: 3
- Berths: 6
- From €25000 to €29000 per week
BOATBOOKINGS SAYS:
"You will surely enjoy your time soaking up the Caribbean and Sardinian sun while bathing in luxury on ARAOK!"
- 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 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!"
- Sunreef 80 Luxury Crewed Catamaran
- Length: 23.87 m
- Year: 2024
- Cabins: 5
- Berths: 10
- From €74000 to €84000 per week
BOATBOOKINGS SAYS:
"The excitement never dies throughout your stay in NALANI while exploring the wonders of Sardinia in Italy!"
- Robertson and Caine 42 Crewed Catamaran
- Length: 13.11 m
- Year: 2011
- Cabins: 4
- Berths: 7
- From $13950 to $16850 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!"
- Robertson and Caine 43 Crewed Catamaran
- Length: 13.4 m
- Year: 2000 (2022 Refit)
- Cabins: 3
- Berths: 6
- From $12500 to $15500 per week
BOATBOOKINGS SAYS:
"Say yes to a memorable Caribbean cruise on NOVA!"
- 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!"
- Leopard 46 Crewed Catamaran
- Length: 14 m
- Year: 2012
- Cabins: 3
- Berths: 7
- From $16000 to $17500 per week
BOATBOOKINGS SAYS:
"Your camera will never rest from the spectacular sceneries of the Caribbean on SARA!"
- Bali 4.8 Crewed Catamaran
- Length: 14 m
- Year: 2024
- Cabins: 3
- Berths: 6
- From $22500 to $24500 per week
BOATBOOKINGS SAYS:
"Bask and relax in the sunlight with your favorite cocktail blend as you cruise the British Virgin Islands on ALORA!"
- 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."
- Robertson and Caine Leopard 50 Crewed Catamaran
- Length: 15 m
- Year: 2020
- Cabins: 3
- Berths: 6
- From $19000 to $21000 per week
BOATBOOKINGS SAYS:
"Wave your body smoothly like the water while partying in the middle of the Caribbean Leewards on WIND DANCER!"
