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
- Watermaker & A/C Bareboat Catamaran
- Length: 13.6 m
- Year: 2019
- Cabins: 6
- Berths: 8
- From $8760 to $10000 per week
BOATBOOKINGS SAYS:
"Spacious Bali 4.5 available for an exciting charter around the flawless islands of the Exumas."
- 4 Cabins Bareboat Catamaran
- Length: 13.96 m
- Year: 2017
- Cabins: 4
- Berths: 9
- From €5250 to €13670 per week
BOATBOOKINGS SAYS:
"Super for exploring the hidden coves and beaches of the BVI"
- 8 Cabins Bareboat Catamaran
- Length: 15.84 m
- Year: 2015
- Cabins: 8
- Berths: 14
- From €8555 to €16825 per week
BOATBOOKINGS SAYS:
"Still modern and contemporary, this 2015 yacht is supreme for gliding around the BVI"
- 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."
- 6 Cabins Bareboat Catamaran
- 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 Sailing Yacht
- 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."
- Bareboat 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 Sailing Yacht
- 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 Sailing Yacht
- 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 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"
- Bareboat Catamaran
- Length: 14.3 m
- Year: 2010
- Cabins: 8
- Berths: 12
- Enquire for prices
BOATBOOKINGS SAYS:
"Beautiful sailing yacht, ideal for holidays in the Grenadines."
- 3 Cabins Bareboat Sailing Yacht
- 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 + 1 Cabins Bareboat 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."
- 4 + 1 Cabins Bareboat 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 + 2 Cabins Bareboat Sailing Yacht
- Length: 51 m
- Year: 2007
- Cabins: 6
- Berths: 10
- From $4800 to $7500 per week
- 3 Cabins Bareboat Sailing Yacht
- Length: 10.69 m
- Year: 2009
- Cabins: 3
- Berths: 6
- From $2185 to $3035 per week
BOATBOOKINGS SAYS:
"Wonderful sailing boat for up to 6 guests, sail the Caribbean in comfort and style."
- 3 Cabins Bareboat Sailing Yacht
- Length: 11.47 m
- Year: 2008
- Cabins: 3
- Berths: 6
- From $2195 to $3695 per week
- 4 Cabins Bareboat Catamaran
- Length: 11.73 m
- Year: 2018
- Cabins: 4
- Berths: 8
- From $5568 to $6091 per week
BOATBOOKINGS SAYS:
"A brand new 4 cabin catamaran."
- 4 Cabins + 2 Bareboat Catamaran
- Length: 11.9 m
- Year: 2010
- Cabins: 4
- Berths: 8
- From $3775 to $5800 per week
BOATBOOKINGS SAYS:
"The Lavezzi 40 has it all."
- Bareboat Catamaran
- Length: 11.95 m
- Year: 2013
- Cabins: 4
- Berths: 8
- From $3050 to $7300 per week
BOATBOOKINGS SAYS:
"Her sleek lines and modern interior make this a brilliant choice for chartering."
- Bareboat Sailing Yacht
- Length: 11.95 m
- Year: 2010
- Cabins: 6
- Berths: 10
- From $3050 to $7300 per week
BOATBOOKINGS SAYS:
"Sleek lines and a modern interior, a brilliant choice for charter."
- 4 + 2 Cabins Bareboat Catamaran
- Length: 11.95 m
- Year: 2010/2011
- Cabins: 4
- Berths: 10
- From €2600 to €4100 per week
- 4 Cabins Bareboat Catamaran
- Length: 12.94 m
- Year: 2007
- Cabins: 4
- Berths: 8
- From $4295 to $7195 per week
BOATBOOKINGS SAYS:
"A fully loaded and elegant catamaran."
- 4 Cabins Bareboat Sailing Yacht
- Length: 13.11 m
- Year: 2003
- Cabins: 4
- Berths: 8
- From $2310 to $3850 per week
- 3 Cabins Bareboat Sailing Yacht
- Length: 13.26 m
- Year: 2006
- Cabins: 3
- Berths: 6
- From $2750 to $4350 per week
- 3 Cabins Bareboat Sailing Yacht
- Length: 14 m
- Year: 1998
- Cabins: 3
- Berths: 6
- From $2310 to $3850 per week
- 4 Cabins Bareboat Catamaran
- Length: 14.05 m
- Year: 2001
- Cabins: 4
- Berths: 8
- From $3495 to $5995 per week
BOATBOOKINGS SAYS:
"She sails like a dream."
- Bareboat Catamaran
- Length: 15.2 m
- Year: 2011
- Cabins: 5
- Berths: 10
- From $6710 to $7975 per week
BOATBOOKINGS SAYS:
"This Catana 50 Carbon Infusion boasts elegance and and speed."
- 4 + 1 Cabins Bareboat Sailing Yacht
- Length: 51 m
- Year: 2006
- Cabins: 5
- Berths: 9
- From $4195 to $5795 per week
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