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 | Sailing Yachts
- Fountaine Pajot Sanya 57 Luxury Crewed Catamaran
- Length: 17.98 m
- Year: 2015
- Cabins: 5
- Berths: 10
- From $34500 to $40500 per week
BOATBOOKINGS SAYS:
"Come to life on board ALIVE in the spectacular British Virgin Islands!"
- 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 with an amazing crew. You will not be disappointed!"
- Lagoon 630 Luxury Crewed Power Catamaran
- Length: 64 m
- Year: 2018
- Cabins: 4
- Berths: 8
- From $0 to $0 per week
BOATBOOKINGS SAYS:
"MARE BLU is a luxurious alternative to a sailing catamaran, offering a superb charter around the Caribbean islands."
- 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!"
- 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!"
- Lagoon 450 Luxury Crewed Catamaran
- Length: 13.7 m
- Year: 2014
- Cabins: 3
- Berths: 6
- From $16500 to $18500 per week
BOATBOOKINGS SAYS:
"GREAT ADVENTURE is an immaculate catamaran that is perfect for people who love water sports and scuba diving!"
- Lagoon 620 Crewed Catamaran
- Length: 18.9 m
- Year: 2010
- Cabins: 4
- Berths: 8
- From €23000 to €25000 per week
BOATBOOKINGS SAYS:
"One of the best crewed Catamarans on the French Riviera!"
- Lagoon 67 Crewed Power Catamaran
- Length: 20 m
- Year: 2022
- Cabins: 3
- Berths: 6
- From $59000 to $70000 per week
BOATBOOKINGS SAYS:
"Step aboard this stand out crewed catamaran and begin making unforgettable memories in the Virgin Islands with the amazing crew who were awarded Best Crew at the 2022 USVI Yacht Show!"
- Day Charter and Week Long Charter Luxury Crewed Catamaran
- Length: 57 m
- Year: 1995
- Cabins: 4
- Berths: 4
- From $3500 to $12990 per day
BOATBOOKINGS SAYS:
"Fantastic day charter, with the option of chartering for a week in the unrivalled BVI!"
- Swan 82 Luxury Crewed Sailing Yacht
- Length: 24.9 m
- Year: 2012
- Cabins: 3
- Berths: 6
- From $39500 to $42500 per week
BOATBOOKINGS SAYS:
"Built for high performance sailing, whilst offering elegance and opulence both above and below deck!"
- Lagoon 45 Luxury Crewed Catamaran
- Length: 13.72 m
- Year: 2019
- Cabins: 3
- Berths: 6
- From $20000 to $28000 per week
BOATBOOKINGS SAYS:
"Stunning and immaculate catamaran with an experienced, fun crew perfect for exploring the crystal clear waters of the Caribbean!"
- Dufour 48 Luxury Crewed Catamaran
- Length: 14 m
- Year: 2022
- Cabins: 4
- Berths: 8
- From $19000 to $22500 per week
BOATBOOKINGS SAYS:
"Built in 2022 SERENITY, a brand new model catamaran, offers an abundance of space inside and out."
- Lagoon 50 Luxury Crewed Catamaran
- Length: 14.75 m
- Year: 2020
- Cabins: 4
- Berths: 8
- From $25000 to $35000 per week
BOATBOOKINGS SAYS:
"Step aboard onto stunning luxury crewed catamaran, KARMA, and set sail around the beautiful Virgin Islands!"
- Bali 5.4 Luxury Crewed Catamaran
- Length: 16 m
- Year: 2019
- Cabins: 4
- Berths: 8
- From $25000 to $30000 per week
BOATBOOKINGS SAYS:
"Enjoy cruising the Caribbean with this enthusiastic, knowledgeable crew looking after you!"
- Lagoon 620 Crewed Catamaran
- Length: 18 m
- Year: 2020
- Cabins: 5
- Berths: 0
- From €19000 to €38000 per week
BOATBOOKINGS SAYS:
"Charter this stand out Lagoon 62 for a luxurious sailing experience around the Sardinian coast or Caribbean Windwards"
- Lagoon 620 Crewed Catamaran
- Length: 18 m
- Year: 2021
- Cabins: 4
- Berths: 8
- From $39000 to $46000 per week
BOATBOOKINGS SAYS:
"BREIZ-ILE is a luxurious and spacious choice for sailing the Caribbean; you won\'t be disappointed!"
- Trinity 164 Luxury Crewed Motor Yacht
- Length: 50 m
- Year: 2009
- Cabins: 5
- Berths: 12
- From $230000 to $250000 per week
BOATBOOKINGS SAYS:
"Extraordinary Luxury Yacht with palatial interior and an abundance of special features."
- Fountaine Pajot 65 Luxury Crewed Catamaran
- Length: 19.81 m
- Year: 2009
- Cabins: 5
- Berths: 10
- From $35800 to $39800 per week
BOATBOOKINGS SAYS:
"MOBY DICK is the perfect catamaran choice for families, friends, or corporate events."
- Matrix Silhouette 76 Luxury Crewed Catamaran
- Length: 23.16 m
- Year: 2013
- Cabins: 6
- Berths: 12
- From $54950 to $64950 per week
BOATBOOKINGS SAYS:
"This is a unique, huge and extremely successful Catamaran for 12 guests - a Boatbookings favourite in the BVI!"
- Fountaine Pajot Luxury Crewed Catamaran
- Length: 13.94 m
- Year: 2020
- Cabins: 4
- Berths: 8
- From $18000 to $21500 per week
BOATBOOKINGS SAYS:
"Explore the Virgin Islands on board this SAONA 47 to create wonderful memories with family or friends"
- Lagoon 78 Luxury Crewed Catamaran
- Length: 23 m
- Year: 2020
- Cabins: 4
- Berths: 0
- From $50000 to $66000 per week
- Merritt 86 Fishing Boat
- Length: 26.21 m
- Year: 2017
- Cabins: 5
- Berths: 10
- From $70000 to $70000 per week
BOATBOOKINGS SAYS:
"Fishing has never been so luxurious than onboard REEL TIGHT."
- 116 Holland Jachtbouw Luxury Crewed Sailing Yacht
- Length: 35 m
- Year: 2003
- Cabins: 3
- Berths: 6
- From $65000 to $70000 per week
BOATBOOKINGS SAYS:
"Perfect for entertaining family and friends."
- Lagoon 560 Luxury Crewed Catamaran
- Length: 17.07 m
- Year: 2015
- Cabins: 4
- Berths: 8
- From $23000 to $32000 per week
BOATBOOKINGS SAYS:
"Enjoy the amazing blues of the Caribbean on AMAZING BLUE for a holiday you won`t be able to stop talking about!"
- Lagoon Seventy 7 Luxury Crewed Catamaran
- Length: 23.5 m
- Year: 2018
- Cabins: 4
- Berths: 8
- From $57000 to $60000 per week
BOATBOOKINGS SAYS:
"The iconic Lagoon Seventy 7 is a real stand-out yacht!"
- Privilege 78 Luxury Crewed Catamaran
- Length: 23.83 m
- Year: 2017
- Cabins: 3
- Berths: 6
- From $56000 to $75000 per week
BOATBOOKINGS SAYS:
"A spacious catamaran with plenty of entertainment"
- 115ft Valdettaro Luxury Crewed Sailing Yacht
- Length: 35 m
- Year: 1996 - refitted 2011
- Cabins: 5
- Berths: 10
- From $52000 to $68250 per week
BOATBOOKINGS SAYS:
"A luxury yacht offering a great layout for both couples and families"
- 35m Staystill Schooner Luxury Crewed Sailing Yacht
- Length: 35 m
- Year: 1938 - refitted 2010
- Cabins: 4
- Berths: 6
- From $44000 to $49000 per week
BOATBOOKINGS SAYS:
"A beautiful traditional sailing schooner sure to make your charter unforgettable!"
- Royal Huisman 47m Luxury Crewed Sailing Yacht
- Length: 47.42 m
- Year: 1998 (2015 Refit)
- Cabins: 3
- Berths: 6
- From $91000 to $112000 per week
BOATBOOKINGS SAYS:
"A sensational sailing yacht for family adventures around the Caribbean."
