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
User Ratings: Top-rated yachts
- Bareboat Catamaran
- Length: 16.75 m
- Year: 2014
- Cabins: 6
- Berths: 12
- From $7500 to $11775 per week
BOATBOOKINGS SAYS:
"A sleek and spacious Bareboat Catamaran, ideal for charters in the Caribbean."
- 5 Cabins Bareboat Sailing Yacht
- Length: 16.06 m
- Year: 2013
- Cabins: 4
- Berths: 8
- Enquire for prices
BOATBOOKINGS SAYS:
"Perfect for Caribbean charters."
- 6 Cabins
- Length: 12.2 m
- Year: 2017
- Cabins: 6
- Berths: 10
- From €3450 to €8250 per week
BOATBOOKINGS SAYS:
"The brand new Bali 4.0 Catamaran is an exciting new model with all the features for an exciting charter."
- 3 Cabins Bareboat Sailboat
- Length: 14.3 m
- Year: 2011
- Cabins: 3
- Berths: 6
- From $3395 to $4995 per week
BOATBOOKINGS SAYS:
"An award-winning monohull yacht, the Bavaria 45 is a perfect holiday option for island hopping."
- Bareboat Sailing Yacht
- Length: 12.17 m
- Year:
- Cabins: 3
- Berths: 6
- From $1995 to $4950 per week
BOATBOOKINGS SAYS:
"Sail the Caribbean in comfort and speed in this lovely Dufour."
- Charter Catamaran
- Length: 13.61 m
- Year: 2010
- Cabins: 4
- Berths: 8
- From €3630 to €8150 per week
BOATBOOKINGS SAYS:
"Beautiful Lagoon 440 Catamaran, ideal for cruising the Caribbean in comfort and style."
- Bareboat Sailboat
- Length: 15.38 m
- Year: 2014
- Cabins: 7
- Berths: 12
- From $3950 to $5735 per week
BOATBOOKINGS SAYS:
"Exceptional seaworthiness and comfort."
- 3 Cabins Bareboat Sailboat
- Length: 14.9 m
- Year: 2009
- Cabins: 3
- Berths: 6
- From $3995 to $5595 per week
BOATBOOKINGS SAYS:
"The Jeanneau 50DS is a true classic, a swift and sleek sailing vessel."
- 4 + 2 Cabins Bareboat Sailing Catamaran
- Length: 13.1 m
- Year: 2012
- Cabins: 6
- Berths: 10
- From €3100 to €5750 per week
- 4 Cabins Bareboat Catamaran
- Length: 13.3 m
- Year: 2013
- Cabins: 4
- Berths: 10
- From €4968 to €7700 per week
BOATBOOKINGS SAYS:
"Elegance and high performance catamaran available in Grenada"
- GULLY Bareboat Catamaran
- Length: 14.3 m
- Year: 2010
- Cabins: 6
- Berths: 12
- From $3560 to $5825 per week
BOATBOOKINGS SAYS:
"Beautiful sailing yacht, ideal for holidays in the Grenadines."
- 3 Cabins Bareboat Sailboat
- Length: 12.17 m
- Year: 2012
- Cabins: 3
- Berths: 8
- From €1890 to €4900 per week
BOATBOOKINGS SAYS:
"A spacious offering from the Dufour shipyard, the 405 GL is ideal to explore Grenada with family in comfort."
- 4 Cabins Bareboat Catamaran
- Length: 12.37 m
- Year: 2005
- Cabins: 4
- Berths: 10
- Enquire for prices
- 4 + 1 Cabins Bareboat Sailing Catamaran
- Length: 15.13 m
- Year: 2010
- Cabins: 5
- Berths: 9
- From $4595 to $6795 per week
BOATBOOKINGS SAYS:
"The Leopard 46 Catamaran is ideal catamaran for ease of sailing coupled with room to relax."
- 4 + 1 Cabins Bareboat Sailing Catamaran
- Length: 15.13 m
- Year: 2010
- Cabins: 5
- Berths: 9
- From $6995 to $9995 per week
BOATBOOKINGS SAYS:
"The Leopard 46 Catamaran is ideal catamaran for ease of sailing coupled with room to relax."
charter@boatbookings.com
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