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!
- CNB Bordeaux 21m Crewed Sailing Yacht
- Length: 21.36 m
- Year: 2018
- Cabins: 3
- Berths: 6
- From €18000 to €23000 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!"
- YYacht Y7 Crewed Sailing Yacht
- Length: 21.86 m
- Year: 2024
- Cabins: 3
- Berths: 6
- From €24000 to €28500 per week
BOATBOOKINGS SAYS:
"YUME, together with her outstanding crew, will surely amaze you and your group as you gasp with awe while witnessing the Balearics' highlights!"
- Jongert 138 Crewed Sailing Yacht
- Length: 42 m
- Year: 2002 (2024 Refit)
- Cabins: 3
- Berths: 6
- From $90000 per week
BOATBOOKINGS SAYS:
"Glide on enchanting waters and have an exhilarating exploration of the Caribbean waters on ABIDE!"
- Ark Yachts 54m Luxury Crewed Sailing Yacht
- Length: 54 m
- Year: 2013 (2023 Refit)
- Cabins: 13
- Berths: 26
- From €85000 to €95000 per week
BOATBOOKINGS SAYS:
"Time is of the essence so spend it with loved ones discovering the vibrant French Riviera on CHRONOS!"
- 116 Holland Jachtbouw Luxury Crewed Sailing Yacht
- Length: 35 m
- Year: 2003
- Cabins: 3
- Berths: 6
- From $75000 to $86250 per week
BOATBOOKINGS SAYS:
"Perfect for entertaining family and friends."
- 35m Staystill Schooner Luxury Crewed Sailing Yacht
- Length: 35 m
- Year: 1938 - refitted 2010
- Cabins: 4
- Berths: 6
- From $46000 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 €38000 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 $30000 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!"
- 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."
- 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
- 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
- 58.4m Alloy Yachts luxury Crewed Sailing Yacht
- Length: 58.4 m
- Year: 2006 (2022 Refit)
- Cabins: 5
- Berths: 10
- From $225000 to $245000 per week
