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

Displaying: Your Search Results in Windward Islands
LE REVE - Lagoon 620 Owners Version - 3 Cabins - Tortola - St Thomas - Leeward Islands - Virgin Islands
LE REVE
    Lagoon 620 Owners Version - 3 Cabins - Tortola - St Thomas - Leeward Islands - Virgin Islands
  • Lagoon 620 Owners Version Crewed Catamaran
  • Length: 18.89 m
  • Year: 2017
  • Cabins: 3
  • Berths: 6
  • From $34000 to $38000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18.89 m (64' 5")
  • Year: 2017
From $34000 to $38000
per week

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!"

SORANA - Princess 67 - 3 Cabins - BVI - St. Martin - St. Barths - Antigua - Grenadines VIEW 2 REVIEWS 
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."

DIANA - Sunreef 74 - 4 Cabins - Antigua - Caribbean Leeward - Virgin Islands - Carribean Windward
DIANA
    Sunreef 74 - 4 Cabins - Antigua - Caribbean Leeward - Virgin Islands - Carribean Windward
  • Sunreef 74 Luxury Crewed Catamaran
  • Length: 22.56 m
  • Year: 2017
  • Cabins: 4
  • Berths: 8
  • From $49000 to $52500 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 22.56 m (76' )
  • Year: 2017
From $49000 to $52500
per week

BOATBOOKINGS SAYS:
"A well designed luxury catamaran perfect for any occasion."

NEVER ENOUGH - Trinity 157 - 5 Cabins - Bahamas - Nassau - Caribbean - Miami - Florida
NEVER ENOUGH
    Trinity 157 - 5 Cabins - Bahamas - Nassau - Caribbean - Miami - Florida
  • Trinity 157 Luxury Crewed Motor Yacht
  • Length: 47.85 m
  • Year: 2006 (2014 Refit)
  • Cabins: 5
  • Berths: 11
  • From $150000 per week
Details Enquire
  • Berths: 11
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 47.85 m (162' 9")
  • Year: 2006 (2014 Refit)
From $150000
per week

BOATBOOKINGS SAYS:
"This glorious luxury yacht is the perfect charter yacht for guests wanting unadulterated luxury to sail the Caribbean and Bahamas!"

DONA LOLA - Westport 130 - 5 Staterooms - St Martin - St Barths - Anguilla
DONA LOLA
    Westport 130 - 5 Staterooms - St Martin - St Barths - Anguilla
  • Westport 130 Luxury Motor Yacht
  • Length: 39.6 m
  • Year: 2003 (2010 Refit)
  • Cabins: 5
  • Berths: 10
  • From $90000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 39.6 m (134' )
  • Year: 2003 (2010 Refit)
From $90000
per week

BOATBOOKINGS SAYS:
"A special elegant yacht with a 5 star crew"

TUTTO LE MARRANE - Leopard 46 - 5 Cabins - Nassau - Paradise Island - Georgetown - Caribbean - BVI - St Barts
TUTTO LE MARRANE
    Leopard 46 - 5 Cabins - Nassau - Paradise Island - Georgetown - Caribbean - BVI - St Barts
  • Leopard 46 Luxury Crewed Motor Yacht
  • Length: 46.33 m
  • Year: 2011
  • Cabins: 5
  • Berths: 12
  • From $145000 to $165000 per week
Details Enquire
  • Berths: 12
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 46.33 m (157' 1")
  • Year: 2011
From $145000 to $165000
per week

BOATBOOKINGS SAYS:
"This sophisticated motor yacht will take you around the Caribbean in style!"

SOVEREIGN - Newcastle 180 - 6 Cabins - Caribbean - Bahamas - Naples - Sicily - Croatia
SOVEREIGN
    Newcastle 180 - 6 Cabins - Caribbean - Bahamas - Naples - Sicily - Croatia
  • Newcastle 180 Luxury Motor Yacht
  • Length: 36.6 m
  • Year: 2011 (Refit 2017)
  • Cabins: 6
  • Berths: 12
  • From €275000 to €295000 per week
Details Enquire
  • Berths: 12
  • Cabins: 6
  • Crew: Crewed
  • Type: Motor
  • Length: 36.6 m (124' )
  • Year: 2011 (Refit 2017)
From €275000 to €295000
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 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!"

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!"

BAGHEERA - Lagoon 620 - 4 Cabins - Tortola - Virgin Gorda - BVI
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 $30500 to $33500 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18.89 m (64' 5")
  • Year: 2018
From $30500 to $33500
per week

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

MAYRILOU - Sunreef Supreme 68 - 5 Cabins - Cannes - Naples - Sicily - Dubrovnik
MAYRILOU
    Sunreef Supreme 68 - 5 Cabins - Cannes - Naples - Sicily - Dubrovnik
  • Sunreef Supreme 68 Crewed Catamaran
  • Length: 20.73 m
  • Year: 2017
  • Cabins: 5
  • Berths: 10
  • From €43000 to €45000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Catamaran
  • Length: 20.73 m (70' 9")
  • Year: 2017
From €43000 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."

BLU 470 - Feadship 50m - 5 Cabins - Monaco - Cannes - Bahamas - Caribbean
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 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."

Top Rated Yachts
  • NENNE - Fountaine Pajot Victoria 67

    NENNE - Fountaine Pajot Victoria 67

    Details
  • LE REVE - Lagoon 620 Owners Version

    LE REVE - Lagoon 620 Owners Version

    Details
  • PTARMIGAN - Swan 82

    PTARMIGAN - Swan 82

    Details
  • ALIVE! - Fountaine Pajot Sanya 57

    ALIVE! - Fountaine Pajot Sanya 57

    Details
  • VENTANA - Lagoon 52

    VENTANA - Lagoon 52

    Details
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