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 Bareboat; in Windward Islands
LAVIEBEL
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."

Jeanneau 53 - 5 Cabins - St Vincent and the Grenadines
Jeanneau 53
    5 Cabins - St Vincent and the Grenadines
  • 5 Cabins Bareboat Sailing Yacht
  • Length: 16.06 m
  • Year: 2013
  • Cabins: 4
  • Berths: 8
  • Enquire for prices
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Bareboat
  • Type: Sail
  • Length: 16.06 m (54' 9")
  • Year: 2013
Enquire for prices

BOATBOOKINGS SAYS:
"Perfect for Caribbean charters."

Bali 4.0 - 6 Cabins - 2017 - St Vincent and the Grenadines
Bali 4.0
    6 Cabins - 2017 - St Vincent and the Grenadines
  • 6 Cabins
  • 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
Bavaria 45
    3 Cabins - Grenada
  • 3 Cabins Bareboat Sailboat
  • 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."

MANUTEA
MANUTEA
  • Charter 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."

RIOJA
RIOJA
  • Bareboat Sailboat
  • 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 Sailboat
  • 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."

Orana 44 Evolution - 4 + 2  Cabins -  Le Marin - Martinique
Orana 44 Evolution
    4 + 2 Cabins - Le Marin - Martinique
  • 4 + 2 Cabins Bareboat Sailing Catamaran
  • Length: 13.1 m
  • Year: 2012
  • Cabins: 6
  • Berths: 10
  • From €3100 to €5750 per week
Details Enquire
  • Berths: 10
  • Cabins: 6
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 13.1 m (44' 2")
  • Year: 2012
From €3100 to €5750
per week

Helia 44 - 4 Cabins - Grenada
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"

HULLY-GULLY
HULLY
    GULLY
  • GULLY Bareboat Catamaran
  • Length: 14.3 m
  • Year: 2010
  • Cabins: 6
  • Berths: 12
  • From $3560 to $9215 per week
Details Enquire
  • Berths: 12
  • Cabins: 6
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 14.3 m (48' 2")
  • Year: 2010
From $3560 to $9215
per week

BOATBOOKINGS SAYS:
"Beautiful sailing yacht, ideal for holidays in the Grenadines."

Dufour 405 Grand Large - 3 Cabins - Grenada
Dufour 405 Grand Large
    3 Cabins - Grenada
  • 3 Cabins Bareboat Sailboat
  • 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."

Lagoon 410 - 4 Cabins - Grenada
Lagoon 410
    4 Cabins - Grenada
  • 4 Cabins Bareboat Catamaran
  • Length: 12.37 m
  • Year: 2005
  • Cabins: 4
  • Berths: 10
  • Enquire for prices
Details Enquire
  • Berths: 10
  • Cabins: 4
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 12.37 m (42' 1")
  • Year: 2005
Enquire for prices

Leopard 46 - 4 + 1 Cabins - St Vincent - Grenada - The Grenadines
Leopard 46
    4 + 1 Cabins - St Vincent - Grenada - The Grenadines
  • 4 + 1 Cabins Bareboat Sailing 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."

Leopard 46 - 4 + 1 Cabins - Grenada
Leopard 46
    4 + 1 Cabins - Grenada
  • 4 + 1 Cabins Bareboat Sailing 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."

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