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

Bali 4.5
    Watermaker & A/C - 4 + 2 (4 double 2 single) - 2019 - Nassau
  • Watermaker & A/C Bareboat Catamaran
  • Length: 13.6 m
  • Year: 2019
  • Cabins: 6
  • Berths: 8
  • From $8760 to $10000 per week
Details Enquire
  • Berths: 8
  • Cabins: 6
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 13.6 m (46' 4")
  • Year: 2019
From $8760 to $10000
per week

BOATBOOKINGS SAYS:
"Spacious Bali 4.5 available for an exciting charter around the flawless islands of the Exumas."

Lagoon 450 F Luxe
    4 Cabins - 2017 - Tortola
  • 4 Cabins Bareboat Catamaran
  • Length: 13.96 m
  • Year: 2017
  • Cabins: 4
  • Berths: 9
  • From €5250 to €13670 per week
Details Enquire
  • Berths: 9
  • Cabins: 4
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 13.96 m (47' 4")
  • Year: 2017
From €5250 to €13670
per week

BOATBOOKINGS SAYS:
"Super for exploring the hidden coves and beaches of the BVI"

Lagoon 52
    8 Cabins - 2015 - Bahamas - Tortola
  • 8 Cabins Bareboat Catamaran
  • Length: 15.84 m
  • Year: 2015
  • Cabins: 8
  • Berths: 14
  • From €8555 to €16825 per week
Details Enquire
  • Berths: 14
  • Cabins: 8
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 15.84 m (53' )
  • Year: 2015
From €8555 to €16825
per week

BOATBOOKINGS SAYS:
"Still modern and contemporary, this 2015 yacht is supreme for gliding around the BVI"

LAVIEBEL
  • Bareboat Catamaran
  • Length: 16.75 m
  • Year: 2014
  • Cabins: 6
  • Berths: 12
  • From $7500 to $11775 per week
Details Enquire
  • Berths: 12
  • Cabins: 6
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 16.75 m (56' 7")
  • Year: 2014
From $7500 to $11775
per week

BOATBOOKINGS SAYS:
"A sleek and spacious Bareboat Catamaran, ideal for charters in the Caribbean."

Bali 4.0
    6 Cabins - 2017 - St Vincent and the Grenadines
  • 6 Cabins Bareboat Catamaran
  • Length: 12.2 m
  • Year: 2017
  • Cabins: 6
  • Berths: 10
  • From €3450 to €8250 per week
Details Enquire
  • Berths: 10
  • Cabins: 6
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 12.2 m (41' 8")
  • Year: 2017
From €3450 to €8250
per week

BOATBOOKINGS SAYS:
"The brand new Bali 4.0 Catamaran is an exciting new model with all the features for an exciting charter."

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."

MANUTEA
  • Bareboat Catamaran
  • Length: 13.61 m
  • Year: 2010
  • Cabins: 4
  • Berths: 8
  • From €3630 to €8150 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 13.61 m (46' 5")
  • Year: 2010
From €3630 to €8150
per week

BOATBOOKINGS SAYS:
"Beautiful Lagoon 440 Catamaran, ideal for cruising the Caribbean in comfort and style."

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."

Fountaine Pajot Helia 44
    4 Cabins - Grenada
  • 4 Cabins Bareboat Catamaran
  • Length: 13.3 m
  • Year: 2013
  • Cabins: 4
  • Berths: 10
  • From €4968 to €7700 per week
Details Enquire
  • Berths: 10
  • Cabins: 4
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 13.3 m (45' 10")
  • Year: 2013
From €4968 to €7700
per week

BOATBOOKINGS SAYS:
"Elegance and high performance catamaran available in 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."

Leopard 46
    4 + 1 Cabins - Grenada
  • 4 + 1 Cabins Bareboat Catamaran
  • Length: 15.13 m
  • Year: 2010
  • Cabins: 5
  • Berths: 9
  • From $6995 to $9995 per week
Details Enquire
  • Berths: 9
  • Cabins: 5
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 15.13 m (51' 1")
  • Year: 2010
From $6995 to $9995
per week

BOATBOOKINGS SAYS:
"The Leopard 46 Catamaran is ideal catamaran for ease of sailing coupled with room to relax."

Leopard 46
    4 + 1 Cabins - St Vincent - Grenada - The Grenadines
  • 4 + 1 Cabins Bareboat Catamaran
  • Length: 15.13 m
  • Year: 2010
  • Cabins: 5
  • Berths: 9
  • From $4595 to $6795 per week
Details Enquire
  • Berths: 9
  • Cabins: 5
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 15.13 m (51' 1")
  • Year: 2010
From $4595 to $6795
per week

BOATBOOKINGS SAYS:
"The Leopard 46 Catamaran is ideal catamaran for ease of sailing coupled with room to relax."

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."

Lucia 40
    4 Cabins - 2018 - Annapolis - Grenadines
  • 4 Cabins Bareboat Catamaran
  • Length: 11.73 m
  • Year: 2018
  • Cabins: 4
  • Berths: 8
  • From $5568 to $6091 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 11.73 m (39' 9")
  • Year: 2018
From $5568 to $6091
per week

BOATBOOKINGS SAYS:
"A brand new 4 cabin catamaran."

SWING
  • Bareboat Sailing Yacht
  • Length: 11.95 m
  • Year: 2010
  • Cabins: 6
  • Berths: 10
  • From $3050 to $7300 per week
Details Enquire
  • Berths: 10
  • Cabins: 6
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 11.95 m (40' 7")
  • Year: 2010
From $3050 to $7300
per week

BOATBOOKINGS SAYS:
"Sleek lines and a modern interior, a brilliant choice for charter."

KIA ORA
  • Bareboat Catamaran
  • Length: 11.95 m
  • Year: 2013
  • Cabins: 4
  • Berths: 8
  • From $3050 to $7300 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 11.95 m (40' 7")
  • Year: 2013
From $3050 to $7300
per week

BOATBOOKINGS SAYS:
"Her sleek lines and modern interior make this a brilliant choice for chartering."

Lagoon 430
    4 Cabins - Grenada
  • 4 Cabins Bareboat Catamaran
  • Length: 12.94 m
  • Year: 2007
  • Cabins: 4
  • Berths: 8
  • From $4295 to $7195 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 12.94 m (44' 10")
  • Year: 2007
From $4295 to $7195
per week

BOATBOOKINGS SAYS:
"A fully loaded and elegant catamaran."

PARANA
  • Bareboat Catamaran
  • Length: 15.2 m
  • Year: 2011
  • Cabins: 5
  • Berths: 10
  • From $6710 to $7975 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 15.2 m (51' 8")
  • Year: 2011
From $6710 to $7975
per week

BOATBOOKINGS SAYS:
"This Catana 50 Carbon Infusion boasts elegance and and speed."

Top Rated Yachts
Charter destinations
  Click for larger map Mexico Yacht Charter South Pacific Yacht Charter Indian Ocean Yacht Charter including Seychelles and Maldives South East Asia Yacht Charter Mediterranean Sea Charter Northern Europe USA East Coast Brazil Charter Yachts Caribbean Yacht Charter Pacific Northwest Charter Yachts
Facebook Twitter Pinterest Youtube Instagram Linkedin

This website uses cookies --- I understand and accept