Windward Islands Charter Yachts and Sailing Vacations

Windward Islands Charter Yachts
Wonderful Windward

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.

See our Windward islands Yacht Charter 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
User Ratings:   Top-rated yachts

THALIMA
    Southern Wind Shipyard SW110 - 4 Cabins - Caribbean Leeward - Windward - Cannes - Sardinia - Monaco
  • Southern Wind Shipyard SW110 Luxury Crewed Sailing Yacht
  • Length: 33.7 m
  • Year: 2010
  • Cabins: 4
  • Berths: 8
  • From €58000 to €64000 per week
VIEW 2 REVIEWS  Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Sail
  • Length: 33.7 m (114' 10")
  • Year: 2010
VIEW 2 REVIEWS
From €58000 to €64000
per week

BOATBOOKINGS SAYS:
"A superb sailing yacht with an outstanding crew. Do not avoid this winter in the Caribbean or next summer in Sardinia!"

CALLISTA
    Lagoon 620 - 4 Cabins - Tortola - BVI - Grenadines
  • Lagoon 620 Luxury Crewed Catamaran
  • Length: 18.89 m
  • Year: 2016
  • Cabins: 4
  • Berths: 8
  • From $33550 to $39600 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18.89 m (64' 5")
  • Year: 2016
VIEW 1 REVIEW
From $33550 to $39600
per week

BOATBOOKINGS SAYS:
"If youre looking for a full spec, diving, state-of-the-art Lagoon 620 with an expert crew, look no further."

ALIVE!
    Fountaine Pajot Sanya 57 - 5 Cabins - BVI - Tortola - Jost Van Dyke - Peter Island - Anegada
  • Fountaine Pajot Sanya 57 Luxury Crewed Catamaran
  • Length: 17.98 m
  • Year: 2015
  • Cabins: 5
  • Berths: 10
  • From $34500 to $40500 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Catamaran
  • Length: 17.98 m (61' 10")
  • Year: 2015
VIEW 1 REVIEW
From $34500 to $40500
per week

BOATBOOKINGS SAYS:
"Come to life on board ALIVE in the spectacular British Virgin Islands!"

LE REVE
    Lagoon 620 Owners Version - 3 Cabins - Tortola - St Thomas - Leeward Islands - Virgin Islands
  • Lagoon 620 Owners Version Luxury Crewed Catamaran
  • Length: 18.89 m
  • Year: 2017
  • Cabins: 3
  • Berths: 6
  • From $35700 to $42000 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18.89 m (64' 5")
  • Year: 2017
VIEW 1 REVIEW
From $35700 to $42000
per week

BOATBOOKINGS SAYS:
"LE REVE is the leading 3 cabin crewed catamaran in the BVI with an amazing crew. You will not be disappointed!"

SORANA
    Princess 67 - 3 Cabins - BVI - St. Martin - St. Barths - Antigua - Grenadines
  • Princess 67 Luxury Crewed Motor Yacht
  • Length: 20.42 m
  • Year: 2008
  • Cabins: 3
  • Berths: 6
  • From $20000 to $26000 per week
VIEW 2 REVIEWS  Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Motor
  • Length: 20.42 m (69' 2")
  • Year: 2008
VIEW 2 REVIEWS
From $20000 to $26000
per week

BOATBOOKINGS SAYS:
"Enjoy al fresco dining with stunning views of the Caribbean coastline."

MARE BLU
    Lagoon 630 - 4 Cabins - Grenadines - Tortola - St Marten - BVI
  • Lagoon 630 Luxury Crewed Power Catamaran
  • Length: 64 m
  • Year: 2018
  • Cabins: 4
  • Berths: 8
  • From $36000 to $39000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 64 m (217' 4")
  • Year: 2018
From $36000 to $39000
per week

BOATBOOKINGS SAYS:
"MARE BLU is a luxurious alternative to a sailing catamaran, offering a superb charter around the Caribbean islands."

ECLIPSE
    Lagoon 620 - 4 Cabins - BVI - Tortola - Virgin Gorda - St Thomas
  • Lagoon 620 Luxury Crewed Catamaran
  • Length: 18.89 m
  • Year: 2016 (2017 Refit)
  • Cabins: 4
  • Berths: 8
  • From $33000 to $37000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18.89 m (64' 5")
  • Year: 2016 (2017 Refit)
From $33000 to $37000
per week

BOATBOOKINGS SAYS:
"ECLIPSE is the perfect way to explore the British Virgin Islands with friends and family this season!"

BLUE PEPPER
    Fountaine Pajot Ipanema 58 - 5 Cabins - Leeward Islands - Virgin Islands - BVI
  • Fountaine Pajot Ipanema 58 Crewed Catamaran
  • Length: 18.28 m
  • Year: 2018
  • Cabins: 5
  • Berths: 10
  • From $35640 to $41480 per week
VIEW 2 REVIEWS  Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18.28 m (62' 4")
  • Year: 2018
VIEW 2 REVIEWS
From $35640 to $41480
per week

BOATBOOKINGS SAYS:
"Outstanding is the word for this crewed catamaran - just have a look at the reviews from clients!"

ZINGARA
    Matrix Silhouette 76 - 5 Cabins - Tortola - Peter Island - Virgin Gorda - Jost Van Dyke - Anegada
  • Matrix Silhouette 76 Luxury Crewed Catamaran
  • Length: 22.34 m
  • Year: 2006 (2017 Refit)
  • Cabins: 5
  • Berths: 10
  • From $42800 to $49100 per week
VIEW 2 REVIEWS  Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Catamaran
  • Length: 22.34 m (75' 2")
  • Year: 2006 (2017 Refit)
VIEW 2 REVIEWS
From $42800 to $49100
per week

BOATBOOKINGS SAYS:
"Zingara never ceases to please those looking for quality sailing and deluxe comfort!"

EXODUS
    Fountaine Pajot Ipanema 58 - BVI - Leeward Islands - Windward Islands
  • Fountaine Pajot Ipanema 58 Luxury Crewed Catamaran
  • Length: 18 m
  • Year: 2015
  • Cabins: 4
  • Berths: 8
  • From $26000 to $30000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18 m (61' )
  • Year: 2015
From $26000 to $30000
per week

BOATBOOKINGS SAYS:
"This stunning crewed catamaran is ideal for a luxurious charter holiday around the Caribbean with a fantastic Chef!"

GREAT ADVENTURE
    Lagoon 450 - 3 Cabins - Caribbean - US Virgin Islands - Windward Islands - Leewards Islands - BVI
  • Lagoon 450 Luxury Crewed Catamaran
  • Length: 13.7 m
  • Year: 2014
  • Cabins: 3
  • Berths: 6
  • From $15000 to $18500 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 13.7 m (46' 2")
  • Year: 2014
From $15000 to $18500
per week

BOATBOOKINGS SAYS:
"GREAT ADVENTURE is an immaculate catamaran that is perfect for people who love water sports and scuba diving!"

LOON
    Newcastle 180 - 6 Cabins - Caribbean - Bahamas - Naples - Sicily - Croatia
  • Newcastle 180 Luxury Crewed Motor Yacht
  • Length: 36.6 m
  • Year: 2011 (Refit 2017)
  • Cabins: 6
  • Berths: 12
  • From $280000 to $300000 per week
Details Enquire
  • Berths: 12
  • Cabins: 6
  • Crew: Crewed
  • Type: Motor
  • Length: 36.6 m (124' )
  • Year: 2011 (Refit 2017)
From $280000 to $300000
per week

BOATBOOKINGS SAYS:
"The ultimate luxury escape, with fabulous entertainment areas and a stunning infinity pool."

CROCODILE DADDY
    Lagoon 620 - 4 Cabins - Western Mediteranean - Caribbean - Virgin Islands
  • Lagoon 620 Crewed Catamaran
  • Length: 18.9 m
  • Year: 2010
  • Cabins: 4
  • Berths: 8
  • From €23000 to €25000 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18.9 m (64' 5")
  • Year: 2010
VIEW 1 REVIEW
From €23000 to €25000
per week

BOATBOOKINGS SAYS:
"One of the best crewed Catamarans on the French Riviera!"

BAGHEERA
    Lagoon 620 - 4 Cabins - Tortola - Virgin Gorda - BVI
  • Lagoon 620 Luxury Crewed Catamaran
  • Length: 18.89 m
  • Year: 2018
  • Cabins: 4
  • Berths: 8
  • From $35000 to $39800 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18.89 m (64' 5")
  • Year: 2018
From $35000 to $39800
per week

BOATBOOKINGS SAYS:
"A standout charter yacht with a vastly experienced crew; Alex, Carla and Beatrix will not disappoint!"

Lagoon 57
    Day Charter and Week Long Charter - 2017 - 4 Cabins (4 cabins) - Tortola - BVI
  • Day Charter and Week Long Charter Luxury Crewed Catamaran
  • Length: 57 m
  • Year: 1995
  • Cabins: 4
  • Berths: 4
  • From $3500 to $12990 per day
Details Enquire
  • Berths: 4
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 57 m (193' )
  • Year: 1995
From $3500 to $12990
per day

BOATBOOKINGS SAYS:
"Fantastic day charter, with the option of chartering for a week in the unrivalled BVI!"

ANANDA
    Swan 82 - 3 Cabins - Virgin Gorda - Tortola - St. Marteen - Grenada - Cannes - Monaco
  • Swan 82 Luxury Crewed Sailing Yacht
  • Length: 24.9 m
  • Year: 2012
  • Cabins: 3
  • Berths: 6
  • From $39500 to $42500 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Sail
  • Length: 24.9 m (84' 6")
  • Year: 2012
From $39500 to $42500
per week

BOATBOOKINGS SAYS:
"Built for high performance sailing, whilst offering elegance and opulence both above and below deck!"

MAYRILOU
    Sunreef Supreme 68 - 5 Cabins - Cannes - Naples - Sicily - Dubrovnik
  • Sunreef Supreme 68 Luxury Crewed Catamaran
  • Length: 20.73 m
  • Year: 2017
  • Cabins: 5
  • Berths: 10
  • From €38000 to €45000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Catamaran
  • Length: 20.73 m (70' 9")
  • Year: 2017
From €38000 to €45000
per week

BOATBOOKINGS SAYS:
"This state-of-the-art Catamaran is an indisputable game changer. MAYRILOU space and beautiful decor will offer guests uninterrupted peace of mind and comfort."

BLUE GRYPHON
    Prout 83 - 5 Cabins - Leeward Islands - Windward Islands - Virgin Islands
  • Prout 83 Luxury Crewed Catamaran
  • Length: 25.3 m
  • Year: 2013 (2017 Refit)
  • Cabins: 5
  • Berths: 12
  • From $60000 to $74000 per week
Details Enquire
  • Berths: 12
  • Cabins: 5
  • Crew: Crewed
  • Type: Catamaran
  • Length: 25.3 m (86' 10")
  • Year: 2013 (2017 Refit)
From $60000 to $74000
per week

BOATBOOKINGS SAYS:
"Impressive sailing catamaran with vast exterior space!"

BLU 470
    Feadship 50m - 5 Cabins - Monaco - Cannes - Bahamas - Caribbean
  • Feadship 50m Luxury Crewed Motor Yacht
  • Length: 49.68 m
  • Year: 1990 (2014 Refit)
  • Cabins: 5
  • Berths: 10
  • From $185000 to $210000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 49.68 m (168' )
  • Year: 1990 (2014 Refit)
From $185000 to $210000
per week

BOATBOOKINGS SAYS:
"BLU 470 is a fantastic crewed motor yacht for charter in the Mediterranean or Caribbean!"

TRANQUILITY
    Matrix Silhouette 76 - 6 Cabins - BVI - Tortola - Virgin Gorda - Jost Van Dyke
  • Matrix Silhouette 76 Luxury Crewed Catamaran
  • Length: 23.16 m
  • Year: 2013
  • Cabins: 6
  • Berths: 12
  • From $56950 to $59950 per week
VIEW 3 REVIEWS  Details Enquire
  • Berths: 12
  • Cabins: 6
  • Crew: Crewed
  • Type: Catamaran
  • Length: 23.16 m (78' )
  • Year: 2013
VIEW 3 REVIEWS
From $56950 to $59950
per week

BOATBOOKINGS SAYS:
"This is a unique, huge and extremely luxurious Catamaran - a Boatbookings favourite!"

SUR LEAU
    Privilege 74 - 4 Cabins - Virgin Islands - Leeward Islands
  • Privilege 74 Luxury Crewed Catamaran
  • Length: 22.68 m
  • Year: 2011
  • Cabins: 4
  • Berths: 8
  • From $48000 to $54000 per week
VIEW 2 REVIEWS  Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 22.68 m (77' )
  • Year: 2011
VIEW 2 REVIEWS
From $48000 to $54000
per week

BOATBOOKINGS SAYS:
"Queen of the Cats in the BVI - we highly recommend the boat and their crew."

REEL TIGHT
    Merritt 86 - 5 cabins - Boca Raton - Nassau - Virgin Islands - Windwards/Leewards - Mexico
  • Merritt 86 Fishing Boat
  • Length: 26.21 m
  • Year: 2017
  • Cabins: 5
  • Berths: 10
  • From $70000 to $70000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 26.21 m (89' 5")
  • Year: 2017
From $70000 to $70000
per week

BOATBOOKINGS SAYS:
"Fishing has never been so luxurious than onboard REEL TIGHT."

ALEGRIA
    Benetti 44m - 5 Cabins - St Martin - Bahamas - Nassau - Caribbean
  • Benetti 44m Luxury Crewed Motor Yacht
  • Length: 44 m
  • Year: 2010
  • Cabins: 5
  • Berths: 10
  • From $129000 to $129000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 44 m (149' 8")
  • Year: 2010
From $129000 to $129000
per week

BOATBOOKINGS SAYS:
"ARSANA is an ideal motor yacht for chartering with family or friends."

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 $60000 to $65000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Sail
  • Length: 35 m (119' 8")
  • Year: 2003
From $60000 to $65000
per week

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

YES DEAR
    Simonis Voyage 58 - 5 Cabins - Tortola - Virgin Gorda - British Virgin Islands
  • Simonis Voyage 58 Crewed Catamaran
  • Length: 17.05 m
  • Year: 2007
  • Cabins: 5
  • Berths: 10
  • From $19700 to $27000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Catamaran
  • Length: 17.05 m (57' 1")
  • Year: 2007
From $19700 to $27000
per week

BOATBOOKINGS SAYS:
"Excellent yacht, amenities and crew in one of the most sought after winter yachting destinations."

AMAZING BLUES
    Lagoon 560 - 4 Cabins - Tortola - Virgin Gorda - Jost Van Dyke - Norman Island
  • Lagoon 560 Luxury Crewed Catamaran
  • Length: 17.07 m
  • Year: 2015
  • Cabins: 4
  • Berths: 8
  • From $23000 to $32000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 17.07 m (58' 3")
  • Year: 2015
From $23000 to $32000
per week

BOATBOOKINGS SAYS:
"Enjoy the amazing blues of the Caribbean on AMAZING BLUE for a holiday you won`t be able to stop talking about!"

BABAC
    Lagoon Seventy 7 - 4 Cabins - Belize - Placencia - French Polynesia - Tahiti
  • Lagoon Seventy 7 Luxury Crewed Catamaran
  • Length: 23.5 m
  • Year: 2018
  • Cabins: 4
  • Berths: 8
  • From $52000 to $55000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 23.5 m (79' 10")
  • Year: 2018
From $52000 to $55000
per week

BOATBOOKINGS SAYS:
"The iconic Lagoon Seventy 7 is a real stand-out yacht!"

NAMASTE
    Privilege 78 - 3 Cabins - Tortola - Virgin Islands - French Polynesia - Fiji - New Zealand
  • Privilege 78 Luxury Crewed Catamaran
  • Length: 23.83 m
  • Year: 2017
  • Cabins: 3
  • Berths: 6
  • From $56000 to $75000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 23.83 m (81' 7")
  • Year: 2017
From $56000 to $75000
per week

BOATBOOKINGS SAYS:
"A spacious catamaran with plenty of entertainment"

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 $42000 to $48000 per week
Details Enquire
  • Berths: 6
  • Cabins: 4
  • Crew: Crewed
  • Type: Sail
  • Length: 35 m (119' 8")
  • Year: 1938 - refitted 2010
From $42000 to $48000
per week

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

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