Windward Islands Charter Yachts and Sailing Vacations 2025-2026

Windward Islands Charter Yachts
A Stunning Beach in the Windward Islands

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!

MAHINA 3 - CNB Bordeaux 21m - 3 Cabins - Cap d'Agde - Porto Cervo - La Maddalena - Sardinia - Italy
MAHINA 3
    CNB Bordeaux 21m - 3 Cabins - Cap d'Agde - Porto Cervo - La Maddalena - Sardinia - Italy
  • CNB Bordeaux 21m Crewed Sailing Yacht
  • Length: 21.36 m
  • Year: 2018
  • Cabins: 3
  • Berths: 6
  • From €18000 to €23000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Sail
  • Length: 21.36 m (72' )
  • Year: 2018
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!"

YUME - YYacht Y7 - 3 Cabins - Palma - Mallorca - Ibiza - Balearics - Spain
YUME
    YYacht Y7 - 3 Cabins - Palma - Mallorca - Ibiza - Balearics - Spain
  • YYacht Y7 Crewed Sailing Yacht
  • Length: 21.86 m
  • Year: 2024
  • Cabins: 3
  • Berths: 6
  • From €24000 to €28500 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Sail
  • Length: 21.86 m (74' 2")
  • Year: 2024
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!"

ABIDE - Jongert 138 - 4 Cabins - St Martin - St Barths - Leewards - Caribbean
ABIDE
    Jongert 138 - 4 Cabins - St Martin - St Barths - Leewards - Caribbean
  • Jongert 138 Crewed Sailing Yacht
  • Length: 42 m
  • Year: 2002 (2024 Refit)
  • Cabins: 3
  • Berths: 6
  • From $90000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Sail
  • Length: 42 m (142' )
  • Year: 2002 (2024 Refit)
From $90000
per week

BOATBOOKINGS SAYS:
"Glide on enchanting waters and have an exhilarating exploration of the Caribbean waters on ABIDE!"

CHRONOS - Ark Yachts 54m - 13 Cabins - Cannes - Nice - St Tropez - Antibes - French Riviera
CHRONOS
    Ark Yachts 54m - 13 Cabins - Cannes - Nice - St Tropez - Antibes - French Riviera
  • Ark Yachts 54m Luxury Crewed Sailing Yacht
  • Length: 54 m
  • Year: 2013 (2023 Refit)
  • Cabins: 13
  • Berths: 26
  • From €85000 to €95000 per week
Details Enquire
  • Berths: 26
  • Cabins: 13
  • Crew: Crewed
  • Type: Sail
  • Length: 54 m (183' )
  • Year: 2013 (2023 Refit)
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!"

WHISPER - 116 Holland Jachtbouw - 3 Staterooms - New England - Caribbean - St Maarteen - Virgin Islands
WHISPER
    116 Holland Jachtbouw - 3 Staterooms - New England - Caribbean - St Maarteen - Virgin Islands
  • 116 Holland Jachtbouw Luxury Crewed Sailing Yacht
  • Length: 35 m
  • Year: 2003
  • Cabins: 3
  • Berths: 6
  • From $75000 to $86250 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Sail
  • Length: 35 m (119' 8")
  • Year: 2003
From $75000 to $86250
per week

BOATBOOKINGS SAYS:
"Perfect for entertaining family and friends."

EROS - 35m Staystill Schooner - 4 Cabins - New England - Newport,RI - Caribbean - BVIs
EROS
    35m Staystill Schooner - 4 Cabins - New England - Newport, RI - Caribbean - BVIs
  • 35m Staystill Schooner Luxury Crewed Sailing Yacht
  • Length: 35 m
  • Year: 1938 - refitted 2010
  • Cabins: 4
  • Berths: 6
  • From $46000 to $49000 per week
Details Enquire
  • Berths: 6
  • Cabins: 4
  • Crew: Crewed
  • Type: Sail
  • Length: 35 m (119' 8")
  • Year: 1938 - refitted 2010
From $46000 to $49000
per week

BOATBOOKINGS SAYS:
"A beautiful traditional sailing schooner sure to make your charter unforgettable!"

HYPERION - Royal Huisman 47m - 3 Cabins - Bahamas - Leeward Islands - Windward Islands
HYPERION
    Royal Huisman 47m - 3 Cabins - Bahamas - Leeward Islands - Windward Islands
  • 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
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Sail
  • Length: 47.42 m (161' 2")
  • Year: 1998 (2015 Refit)
From $112000 to $125000
per week

BOATBOOKINGS SAYS:
"A sensational sailing yacht for family adventures around the Caribbean."

CHAMPAGNE HIPPY - Oyster 825 - 4 Cabins - Palma de Mallorca - Menorca - Ibiza
CHAMPAGNE HIPPY
    Oyster 825 - 4 Cabins - Palma de Mallorca - Menorca - Ibiza
  • Oyster 825 Crewed Sailing Yacht
  • Length: 25 m
  • Year: 2014
  • Cabins: 0
  • Berths: 8
  • From €30000 to €38000 per week
Details Enquire
  • Berths: 8
  • Cabins: 0
  • Crew: Crewed
  • Type: Sail
  • Length: 25 m (85' 4")
  • Year: 2014
From €30000 to €38000
per week

BOATBOOKINGS SAYS:
"A perfect boat for sailing with family!"

HELIOS - Perini Navi 45m - 4 Cabins - Leeward Islands - Virgin Islands - Croatia - Sicily
HELIOS
    Perini Navi 45m - 4 Cabins - Leeward Islands - Virgin Islands - Croatia - Sicily
  • Perini Navi 45m Luxury Crewed Sailing Yacht
  • Length: 45.3 m
  • Year: 2007 (2016 Refit)
  • Cabins: 4
  • Berths: 10
  • From $150000 per week
Details Enquire
  • Berths: 10
  • Cabins: 4
  • Crew: Crewed
  • Type: Sail
  • Length: 45.3 m (154' 6")
  • Year: 2007 (2016 Refit)
From $150000
per week

BOATBOOKINGS SAYS:
"One of our favourite Perini Navi sailing yachts, ideal for Caribbean getaways"

XIMERA - Hanse 575 - 3 Cabins - Virgin Islands - Leeward Islands - Windward Islands
XIMERA
    Hanse 575 - 3 Cabins - Virgin Islands - Leeward Islands - Windward Islands
  • Hanse 575 Luxury Crewed Sailing Yacht
  • Length: 17.5 m
  • Year: 2014
  • Cabins: 3
  • Berths: 6
  • From $14000 to $16000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Sail
  • Length: 17.5 m (59' 10")
  • Year: 2014
From $14000 to $16000
per week

BOATBOOKINGS SAYS:
"An intimate sailing yacht with a superb crew"

SALAMANDER - Nauticat 58 - 2 Cabins - Grenada - Bequia - Leewards - Windwards - Martinique
SALAMANDER
    Nauticat 58 - 2 Cabins - Grenada - Bequia - Leewards - Windwards - Martinique
  • Nauticat 58 Luxury Crewed Sailing Yacht
  • Length: 17.68 m
  • Year: 1987 (2014 Refit)
  • Cabins: 2
  • Berths: 4
  • From $11335 to $5695 per week
Details Enquire
  • Berths: 4
  • Cabins: 2
  • Crew: Crewed
  • Type: Sail
  • Length: 17.68 m (60' 4")
  • Year: 1987 (2014 Refit)
From $11335 to $5695
per week

BOATBOOKINGS SAYS:
"Stunning sailing yacht available in the Grenadines!"

THE ROYAL BLUE - Hylass 70 - 3 Cabins - St. Thomas - Tortola - US Virgin Islands - British Virgin Islands - Grenadines - Windwards - Leewards - Caribbean
THE ROYAL BLUE
    Hylass 70 - 3 Cabins - St. Thomas - Tortola - US Virgin Islands - British Virgin Islands - Grenadines - Windwards - Leewards - Caribbean
  • Hylass 70 Crewed Sailing Yacht
  • Length: 21.34 m
  • Year: 2009
  • Cabins: 3
  • Berths: 6
  • From $17000 to $19000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Sail
  • Length: 21.34 m (72' 10")
  • Year: 2009
From $17000 to $19000
per week

BOATBOOKINGS SAYS:
"Experience a royal treatment aboard THE ROYAL BLUE in your Caribbean sailing yacht charter."

CAP II - CNB 76 Sloop - 4 Cabins - Virgin Islands - Leeward Islands - Windward Islands
CAP II
    CNB 76 Sloop - 4 Cabins - Virgin Islands - Leeward Islands - Windward Islands
  • 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
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Sail
  • Length: 22.34 m (75' 2")
  • Year: 1992 - extensive refit 2006
From $26000 to $30000
per week

BOATBOOKINGS SAYS:
"CAP II is definitely one of the most impressive vessels available in the Caribbean!"

VIVID - Jongert 2700M - 3 Cabins - Falmouth - Solent - Isle of Wight - Isles of Scilly - Channel Islands - Caribbean
VIVID
    Jongert 2700M - 3 Cabins - Falmouth - Solent - Isle of Wight - Isles of Scilly - Channel Islands - Caribbean
  • Jongert 2700M Crewed Sailing Yacht
  • Length: 26.8 m
  • Year: 2001
  • Cabins: 3
  • Berths: 6
  • From €28000 to €34000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Sail
  • Length: 26.8 m (91' 4")
  • Year: 2001
From €28000 to €34000
per week

BOATBOOKINGS SAYS:
"Vivid is a stylish yacht to sail in!"

LUNA - Perini Navi 52m - 5 Cabins - Leeward Islands - Caribbean - Monaco - Cannes - San Remo - Sardinia
LUNA
    Perini Navi 52m - 5 Cabins - Leeward Islands - Caribbean - Monaco - Cannes - San Remo - Sardinia
  • Perini Navi 52m Luxury Crewed Sailing Yacht
  • Length: 52 m
  • Year: 1997 (2007 Refit)
  • Cabins: 5
  • Berths: 10
  • From €175000 to €189000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Sail
  • Length: 52 m (176' 4")
  • Year: 1997 (2007 Refit)
From €175000 to €189000
per week

BOATBOOKINGS SAYS:
"Her spacious flybridge is almost full-beam in width and is ideal for alfresco dining!"

Bavaria 45 - 3 Cabins - Grenada
Bavaria 45
    3 Cabins - Grenada
  • 3 Cabins Bareboat Sailing Yacht
  • Length: 14.3 m
  • Year: 2011
  • Cabins: 3
  • Berths: 6
  • From $3395 to $4995 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 14.3 m (48' 2")
  • Year: 2011
From $3395 to $4995
per week

BOATBOOKINGS SAYS:
"An award-winning monohull yacht, the Bavaria 45 is a perfect holiday option for island hopping."

THOXA VII
THOXA VII
  • Bareboat Sailing Yacht
  • Length: 12.17 m
  • Year:
  • Cabins: 3
  • Berths: 6
  • From $1995 to $4950 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 12.17 m (41' 5")
  • Year:
From $1995 to $4950
per week

BOATBOOKINGS SAYS:
"Sail the Caribbean in comfort and speed in this lovely Dufour."

RIOJA
RIOJA
  • Bareboat Sailing Yacht
  • Length: 15.38 m
  • Year: 2014
  • Cabins: 7
  • Berths: 12
  • From $3950 to $5735 per week
Details Enquire
  • Berths: 12
  • Cabins: 7
  • Crew: Bareboat
  • Type: Sail
  • Length: 15.38 m (52' 2")
  • Year: 2014
From $3950 to $5735
per week

BOATBOOKINGS SAYS:
"Exceptional seaworthiness and comfort."

Jeanneau 50DS - 3 Cabins - Grenada
Jeanneau 50DS
    3 Cabins - Grenada
  • 3 Cabins Bareboat Sailing Yacht
  • Length: 14.9 m
  • Year: 2009
  • Cabins: 3
  • Berths: 6
  • From $3995 to $5595 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 14.9 m (50' 2")
  • Year: 2009
From $3995 to $5595
per week

BOATBOOKINGS SAYS:
"The Jeanneau 50DS is a true classic, a swift and sleek sailing vessel."

Dufour 405 Grand Large - 3 Cabins - Grenada
Dufour 405 Grand Large
    3 Cabins - Grenada
  • 3 Cabins Bareboat Sailing Yacht
  • Length: 12.17 m
  • Year: 2012
  • Cabins: 3
  • Berths: 8
  • From €1890 to €4900 per week
Details Enquire
  • Berths: 8
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 12.17 m (41' 5")
  • Year: 2012
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."

Beneteau 515 - 4 + 2 Cabins - Grenadines
Beneteau 515
    4 + 2 Cabins - Grenadines
  • 4 + 2 Cabins Bareboat Sailing Yacht
  • Length: 51 m
  • Year: 2007
  • Cabins: 6
  • Berths: 10
  • From $4800 to $7500 per week
Details Enquire
  • Berths: 10
  • Cabins: 6
  • Crew: Bareboat
  • Type: Sail
  • Length: 51 m (173' )
  • Year: 2007
From $4800 to $7500
per week

Sun Odyssey 36i - 3 Cabins - Grenada
Sun Odyssey 36i
    3 Cabins - Grenada
  • 3 Cabins Bareboat Sailing Yacht
  • Length: 10.69 m
  • Year: 2009
  • Cabins: 3
  • Berths: 6
  • From $2185 to $3035 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 10.69 m (36' 1")
  • Year: 2009
From $2185 to $3035
per week

BOATBOOKINGS SAYS:
"Wonderful sailing boat for up to 6 guests, sail the Caribbean in comfort and style."

Bavaria 39 - 3 Cabins - Grenada
Bavaria 39
    3 Cabins - Grenada
  • 3 Cabins Bareboat Sailing Yacht
  • Length: 11.47 m
  • Year: 2008
  • Cabins: 3
  • Berths: 6
  • From $2195 to $3695 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 11.47 m (39' 7")
  • Year: 2008
From $2195 to $3695
per week

Jeanneau 43 DS - 4 Cabins - St. Vincent and the Grenadines
Jeanneau 43 DS
    4 Cabins - St. Vincent and the Grenadines
  • 4 Cabins Bareboat Sailing Yacht
  • Length: 13.11 m
  • Year: 2003
  • Cabins: 4
  • Berths: 8
  • From $2310 to $3850 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Bareboat
  • Type: Sail
  • Length: 13.11 m (44' 3")
  • Year: 2003
From $2310 to $3850
per week

Beneteau Cyclades 43 - 3 Cabins - St. Vincent
Beneteau Cyclades 43
    3 Cabins - St. Vincent
  • 3 Cabins Bareboat Sailing Yacht
  • Length: 13.26 m
  • Year: 2006
  • Cabins: 3
  • Berths: 6
  • From $2750 to $4350 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 13.26 m (45' 6")
  • Year: 2006
From $2750 to $4350
per week

Beneteau 463 - 3 Cabins - St. Vincent/Grendines
Beneteau 463
    3 Cabins - St. Vincent/Grendines
  • 3 Cabins Bareboat Sailing Yacht
  • Length: 14 m
  • Year: 1998
  • Cabins: 3
  • Berths: 6
  • From $2310 to $3850 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 14 m (47' 8")
  • Year: 1998
From $2310 to $3850
per week

MIO SHI - Beneteau 51.1 - 3 Cabins - 2021 - Grenada - Bequia - Mustique
MIO SHI
    Beneteau 51.1 - 3 Cabins - 2021 - Grenada - Bequia - Mustique
  • Beneteau 51.1 Crewed Sailing Yacht
  • Length: 16 m
  • Year: 2021
  • Cabins: 3
  • Berths: 0
  • From €13900 to €13900 per week
Details Enquire
  • Berths: 0
  • Cabins: 3
  • Crew: Crewed
  • Type: Sail
  • Length: 16 m (54' 4")
  • Year: 2021
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."

Beneteau 51.5 - 4 + 1 Cabins - Grenada
Beneteau 51.5
    4 + 1 Cabins - Grenada
  • 4 + 1 Cabins Bareboat Sailing Yacht
  • Length: 51 m
  • Year: 2006
  • Cabins: 5
  • Berths: 9
  • From $4195 to $5795 per week
Details Enquire
  • Berths: 9
  • Cabins: 5
  • Crew: Bareboat
  • Type: Sail
  • Length: 51 m (173' )
  • Year: 2006
From $4195 to $5795
per week

PRANA - 58.4m Alloy Yachts - 5 Staterooms - Tortola - St Maarten - Antigua - Monaco - Porto Cervo - Naples
PRANA
    58.4m Alloy Yachts - 5 Staterooms - Tortola - St Maarten - Antigua - Monaco - Porto Cervo - Naples
  • 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
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Sail
  • Length: 58.4 m (198' 8")
  • Year: 2006 (2022 Refit)
From $225000 to $245000
per week

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