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
User Ratings:   Top-rated yachts

Displaying: Your Search Results in Windward Islands
ALIVE! - Fountaine Pajot Sanya 57 - 5 Cabins - BVI - Tortola - Jost Van Dyke - Peter Island - Anegada VIEW 1 REVIEW 
ALIVE!
    Fountaine Pajot Sanya 57 - 5 Cabins - BVI - Tortola - Jost Van Dyke - Peter Island - Anegada
  • Fountaine Pajot Sanya 57 Crewed Catamaran
  • Length: 17.98 m
  • Year: 2015
  • Cabins: 5
  • Berths: 10
  • From $28290 to $31900 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 $28290 to $31900
per week

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

CROCODILE DADDY - Lagoon 620 - 4 Cabins - Western Mediteranean - Caribbean - Virgin Islands VIEW 1 REVIEW 
CROCODILE DADDY
    Lagoon 620 - 4 Cabins - Western Mediteranean - Caribbean - Virgin Islands
  • Lagoon 620 Crewed Sailing Catamaran
  • Length: 18.9 m
  • Year: 2010
  • Cabins: 4
  • Berths: 8
  • From €23000 to €26000 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 €26000
per week

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

RAINBOW - J Class 40m - 3 Cabins - Tortola - Jost Van Dyke - Anguilla
RAINBOW
    J Class 40m - 3 Cabins - Tortola - Jost Van Dyke - Anguilla
  • J Class 40m Luxury Crewed Sailing Yacht
  • Length: 40 m
  • Year: 2012
  • Cabins: 3
  • Berths: 6
  • From €65000 to €70000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Sail
  • Length: 40 m (136' 4")
  • Year: 2012
From €65000 to €70000
per week

BOATBOOKINGS SAYS:
"RAINBOW is the ultimate combination of sophisticated and speed. Sails like a dream!"

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

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

SWALLOWS & AMAZONS - CNB 77 - 4 Cabins - Corsica - Bonifacio - Sardinia VIEW 1 REVIEW 
SWALLOWS & AMAZONS
    CNB 77 - 4 Cabins - Corsica - Bonifacio - Sardinia
  • CNB 77 Crewed Charter Yacht
  • Length: 23.7 m
  • Year: 2009
  • Cabins: 4
  • Berths: 8
  • From $18000 to $25000 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Sail
  • Length: 23.7 m (80' 6")
  • Year: 2009
VIEW 1 REVIEW
From $18000 to $25000
per week

BOATBOOKINGS SAYS:
"This is a superb sailing yacht with a vastly knowledgable crew. Experience Corsica the authentic way, mixed with the charm of Sardinia."

TRANQUILITY - Matrix Silhouette 76 - 6 Cabins - BVI - Tortola - Virgin Gorda - Jost Van Dyke VIEW 3 REVIEWS 
TRANQUILITY
    Matrix Silhouette 76 - 6 Cabins - BVI - Tortola - Virgin Gorda - Jost Van Dyke
  • Matrix Silhouette 76 Crewed Catamaran
  • Length: 23.16 m
  • Year: 2013
  • Cabins: 6
  • Berths: 12
  • From $46950 to $49950 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 $46950 to $49950
per week

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

SOON COME - Sunreef 62 - 4 Cabins - BVI - Tortola - Virgin Gorda - Jost Van Dyke
SOON COME
    Sunreef 62 - 4 Cabins - BVI - Tortola - Virgin Gorda - Jost Van Dyke
  • Sunreef 62 Crewed Sailing Catamaran
  • Length: 18.23 m
  • Year: 2006
  • Cabins: 4
  • Berths: 8
  • From $21500 to $24500 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18.23 m (62' 11")
  • Year: 2006
From $21500 to $24500
per week

BOATBOOKINGS SAYS:
"Sunreef luxury with an accomplished 5* crew. Book early to avoid disappointment."

ULA - Privilege 58 - 3 Cabins - BVI - Tortola - Virgin Gorda - Jost Van Dyke - Anegada
ULA
    Privilege 58 - 3 Cabins - BVI - Tortola - Virgin Gorda - Jost Van Dyke - Anegada
  • Privilege 58 Luxury Crewed Catamaran
  • Length: 18 m
  • Year: 2002
  • Cabins: 3
  • Berths: 6
  • From $20000 to $27000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18 m (61' )
  • Year: 2002
From $20000 to $27000
per week

BOATBOOKINGS SAYS:
"The Rolls Royce of crewed catamarans. Quality crew, amenities and luxurious decorations make for an unbeatable charter."

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 $60000 to $75000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Sail
  • Length: 35 m (119' 8")
  • Year: 2003
From $60000 to $75000
per week

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

YES DEAR - Simonis Voyage 58 - 5 Cabins - Tortola - Virgin Gorda - British Virgin Islands
YES DEAR
    Simonis Voyage 58 - 5 Cabins - Tortola - Virgin Gorda - British Virgin Islands
  • Simonis Voyage 58 Crewed Sailing Catamaran
  • Length: 17.05 m
  • Year: 2007
  • Cabins: 5
  • Berths: 10
  • From $24000 to $26500 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Catamaran
  • Length: 17.05 m (57' 1")
  • Year: 2007
From $24000 to $26500
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
AMAZING BLUES
    Lagoon 560 - 4 Cabins - Tortola - Virgin Gorda - Jost Van Dyke - Norman Island
  • Lagoon 560 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!"

MARAE - Alloy Yacht 33m - 3 Cabins - New England - Newport - Tortola - St Martin - Antigua - Mustique - Canouan
MARAE
    Alloy Yacht 33m - 3 Cabins - New England - Newport - Tortola - St Martin - Antigua - Mustique - Canouan
  • Alloy Yacht 33m Crewed Sailing Yacht
  • Length: 32.9 m
  • Year: 2004 (2014 Refit)
  • Cabins: 3
  • Berths: 7
  • From $54000 to $65000 per week
Details Enquire
  • Berths: 7
  • Cabins: 3
  • Crew: Crewed
  • Type: Sail
  • Length: 32.9 m (111' 2")
  • Year: 2004 (2014 Refit)
From $54000 to $65000
per week

BOATBOOKINGS SAYS:
"Amazing selection of water toys, a Captain who teaches racing on dinghies and a divine Chef make MARAE a must!"

REE - 115ft Valdettaro - 5 Cabins - Caribbean - Italy - French Riviera - Monaco - Turkey - Croatia
REE
    115ft Valdettaro - 5 Cabins - Caribbean - Italy - French Riviera - Monaco - Turkey - Croatia
  • 115ft Valdettaro Luxury Crewed Sailing Yacht
  • Length: 35 m
  • Year: 1996 - refitted 2011
  • Cabins: 5
  • Berths: 10
  • From $70000 to $80000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Sail
  • Length: 35 m (119' 8")
  • Year: 1996 - refitted 2011
From $70000 to $80000
per week

BOATBOOKINGS SAYS:
"A luxury yacht offering a great layout for both couples and families"

PEARL - Dean 5000 - 3 Cabins - BVI - British Virgin Islands - San Blas Islands - Belize VIEW 1 REVIEW 
PEARL
    Dean 5000 - 3 Cabins - BVI - British Virgin Islands - San Blas Islands - Belize
  • Dean 5000 Crewed Sailing Catamaran
  • Length: 15.39 m
  • Year: 2012
  • Cabins: 3
  • Berths: 6
  • From $19000 to $26000 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 15.39 m (52' 3")
  • Year: 2012
VIEW 1 REVIEW
From $19000 to $26000
per week

BOATBOOKINGS SAYS:
"Brilliant value for money with this luxury crewed cat - drinks and dives included!"

LADY MARGARET - Horizon 64 - 1 Cabin - Virgin Islands - Leeward Islands - Windward Islands VIEW 1 REVIEW 
LADY MARGARET
    Horizon 64 - 1 Cabin - Virgin Islands - Leeward Islands - Windward Islands
  • Horizon 64 Crewed Motor Yacht
  • Length: 19.51 m
  • Year: 2008
  • Cabins: 1
  • Berths: 1
  • From $18900 to $20900 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 1
  • Cabins: 1
  • Crew: Crewed
  • Type: Motor
  • Length: 19.51 m (66' 7")
  • Year: 2008
VIEW 1 REVIEW
From $18900 to $20900
per week

BOATBOOKINGS SAYS:
"An ideal charter yacht for a luxurious time in the Caribbean"

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