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!
- 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"
- 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:
"Perfect for smaller groups."
- 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 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
- 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."
- 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."
- 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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