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
- CNB Bordeaux 21m Crewed Sailing Yacht
- Length: 21.36 m
- Year: 2018
- Cabins: 3
- Berths: 6
- From €17000 to €21000 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!"
- 116 Holland Jachtbouw Luxury Crewed Sailing Yacht
- Length: 35 m
- Year: 2003
- Cabins: 3
- Berths: 6
- From $65000 to $74750 per week
BOATBOOKINGS SAYS:
"Perfect for entertaining family and friends."
- 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 $112000 to $125000 per week
BOATBOOKINGS SAYS:
"A sensational sailing yacht for family adventures around the Caribbean."
- Oyster 825 Crewed Sailing Yacht
- Length: 25 m
- Year: 2014
- Cabins: 0
- Berths: 8
- From €30000 to €36300 per week
BOATBOOKINGS SAYS:
"A perfect boat for sailing with family!"
- Perini Navi 45m Luxury Crewed Sailing Yacht
- Length: 45.3 m
- Year: 2007 (2016 Refit)
- Cabins: 4
- Berths: 10
- From $150000 per week
BOATBOOKINGS SAYS:
"One of our favourite Perini Navi sailing yachts, ideal for Caribbean getaways"
- Hanse 575 Luxury Crewed Sailing Yacht
- Length: 17.5 m
- Year: 2014
- Cabins: 3
- Berths: 6
- From $14000 to $16000 per week
BOATBOOKINGS SAYS:
"An intimate sailing yacht with a superb crew"
- Nauticat 58 Luxury Crewed Sailing Yacht
- Length: 17.68 m
- Year: 1987 (2014 Refit)
- Cabins: 2
- Berths: 4
- From $11335 to $5695 per week
BOATBOOKINGS SAYS:
"Stunning sailing yacht available in the Grenadines!"
- Hylass 70 Crewed Sailing Yacht
- Length: 21.34 m
- Year: 2009
- Cabins: 3
- Berths: 6
- From $17000 to $19000 per week
BOATBOOKINGS SAYS:
"Experience a royal treatment aboard THE ROYAL BLUE in your Caribbean sailing yacht charter."
- CNB 76 Sloop Luxury Crewed Sailing Yacht
- Length: 22.34 m
- Year: 1992 - extensive refit 2006
- Cabins: 4
- Berths: 8
- From $26000 to $26000 per week
BOATBOOKINGS SAYS:
"CAP II is definitely one of the most impressive vessels available in the Caribbean!"
- Jongert 2700M Crewed Sailing Yacht
- Length: 26.8 m
- Year: 2001
- Cabins: 3
- Berths: 6
- From €28000 to €34000 per week
BOATBOOKINGS SAYS:
"Vivid is a stylish yacht to sail in!"
- Perini Navi 52m Luxury Crewed Sailing Yacht
- Length: 52 m
- Year: 1997 (2007 Refit)
- Cabins: 5
- Berths: 10
- From €175000 to €189000 per week
BOATBOOKINGS SAYS:
"Her spacious flybridge is almost full-beam in width and is ideal for alfresco dining!"
- Alloy 53m Luxury Crewed Sailing Yacht
- Length: 53 m
- Year: 2002 (Refit 2014)
- Cabins: 5
- Berths: 11
- From $175000 per week
BOATBOOKINGS SAYS:
"French Captain with tremendous experience of travelling around the world, excellent Chef and Crew. Very comfortable sailing yacht. Highly recommended by the MD who has had the privilege of sailing aboard her."
- Ark Yachts 180 Luxury Crewed Sailing Yacht
- Length: 60 m
- Year: 2013
- Cabins: 13
- Berths: 26
- From €84000 to €92000 per week
- 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 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."
- 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."
- Hylas 70 Crewed Sailing Yacht
- Length: 21.2 m
- Year: 2011
- Cabins: 3
- Berths: 6
- From $18900 to $24035 per week
BOATBOOKINGS SAYS:
"A modern and elegant yacht."
- 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 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
- Lagoon 46 Feet Luxury Crewed Catamaran
- Length: 14 m
- Year: 2020
- Cabins: 4
- Berths: 10
- From €8394 to €10387 per week
BOATBOOKINGS SAYS:
"The enormous fly-bridge will have your whole family involved in the ancient art of sailing on your charter aboard WESTERLUND!"
- 3 Cabins Bareboat Sailing Yacht
- Length: 14 m
- Year: 1998
- Cabins: 3
- Berths: 6
- From $2310 to $3850 per week
- Beneteau 51.1 Crewed Sailing Yacht
- Length: 16 m
- Year: 2021
- Cabins: 3
- Berths: 0
- From €13900 to €13900 per week
BOATBOOKINGS SAYS:
"The modern and well thought design of MIO SHI is light and spacious, perfect for cruising the Caribbean."
- 4 + 1 Cabins Bareboat Sailing Yacht
- Length: 51 m
- Year: 2006
- Cabins: 5
- Berths: 9
- From $4195 to $5795 per week
