Luxury Yacht Charter in the Leeward Islands

Yacht Charter in the Leeward Islands
Pool with a view!

The Leeward Islands are to the east of Puerto Rico in the Lesser Antilles of the Caribbean. They are some of the most beautiful yachting destinations in the world… offering something for everyone…from pristine, private beaches to chic shops and restaurants. The most notable islands in the Leeward Chain are Anguilla and St Barts - winter favourites for the Jet Set worldwide.

If you are looking for quiet and relaxation, we know where to find it. If you are looking for Caribbean versions of St Tropez packed with activities and other people, the Leewards offer that as well! Everybody wins and everybody is happy here, it is hard not to be when you are surrounded with cheerful vibes, swaying palm trees and a cool summer breeze!

More information on the Leeward Islands

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  |  Sailing Yachts
User Ratings:   Top-rated yachts

Displaying: Your Search Results Bareboat; in Leeward Islands
Dufour 460 GL - 4 cabins - 2017 - Antigua
Dufour 460 GL
    4 cabins - 2017 - Antigua
  • 4 cabins
  • Length: 14 m
  • Year: 2017
  • Cabins: 4
  • Berths: 10
  • Enquire for prices
Details Enquire
  • Berths: 10
  • Cabins: 4
  • Crew: Bareboat
  • Type: Sail
  • Length: 14 m (47' 8")
  • Year: 2017
Enquire for prices

BOATBOOKINGS SAYS:
"This yacht is only available for charter from November 2017 in Antigua."

Dufour 500 - 5 Cabins - 2016 - Antigua
Dufour 500
    5 Cabins - 2016 - Antigua
  • 5 Cabins Bareboat Sailing Yacht
  • Length: 15.24 m
  • Year: 2016
  • Cabins: 5
  • Berths: 10
  • Enquire for prices
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Bareboat
  • Type: Sail
  • Length: 15.24 m (51' )
  • Year: 2016
Enquire for prices

Oceanis 48 - 5 Cabins - Guadeloupe
Oceanis 48
    5 Cabins - Guadeloupe
  • 5 Cabins Bareboat Sailing Yacht
  • Length: 14.6 m
  • Year: 2013
  • Cabins: 5
  • Berths: 12
  • From $2950 to $6900 per week
Details Enquire
  • Berths: 12
  • Cabins: 5
  • Crew: Bareboat
  • Type: Sail
  • Length: 14.6 m (49' 8")
  • Year: 2013
From $2950 to $6900
per week

BOATBOOKINGS SAYS:
"Modern, comfortable and stylish. This Oceanis 48 is beautifully equipped with all the necessities for a successful sailing holiday in the Caribbean!"

Bali 4.5 F - 4 Cabins - 2017 - Antigua
Bali 4.5 F
    4 Cabins - 2017 - Antigua
  • 4 Cabins Bareboat Catamaran
  • Length: 13.6 m
  • Year: 2017
  • Cabins: 4
  • Berths: 8
  • From 3800 to 9785 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 13.6 m (46' 4")
  • Year: 2017
From 3800 to 9785
per week

BOATBOOKINGS SAYS:
"Fantastically modern, this new for 2017 Bali catamaran is stunning"

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."

Lagoon 450 Luxe - 2016 - 4 + 2 Cabins - Antigua
Lagoon 450 Luxe
    2016 - 4 + 2 Cabins - Antigua
  • 2016 Bareboat Sailing Catamaran
  • Length: 14.02 m
  • Year: 2016
  • Cabins: 6
  • Berths: 10
  • From 7500 to 10000 per week
Details Enquire
  • Berths: 10
  • Cabins: 6
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 14.02 m (47' 10")
  • Year: 2016
From 7500 to 10000
per week

BOATBOOKINGS SAYS:
"One of the newest and most modern catamarans on the water!"

Sun Odyssey 469 - 4 Cabins - BVI
Sun Odyssey 469
    4 Cabins - BVI
  • 4 Cabins Bareboat Sailing Yacht
  • Length: 14.05 m
  • Year: 2013
  • Cabins: 4
  • Berths: 8
  • From $4000 to $6000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Bareboat
  • Type: Sail
  • Length: 14.05 m (47' 1")
  • Year: 2013
From $4000 to $6000
per week

BOATBOOKINGS SAYS:
"A brand new vessel perfectly adapted to sail the BVIs!"

Orana 44 - 4 Cabins - Antigua
Orana 44
    4 Cabins - Antigua
  • 4 Cabins Bareboat Sailing Catamaran
  • Length: 13.1 m
  • Year: 2010
  • Cabins: 3
  • Berths: 10
  • Enquire for prices
Details Enquire
  • Berths: 10
  • Cabins: 3
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 13.1 m (44' 2")
  • Year: 2010
Enquire for prices

Sun Odyssey 509 Super Premier - 5 Cabins - Guadeloupe
Sun Odyssey 509 Super Premier
    5 Cabins - Guadeloupe
  • 5 Cabins Bareboat Sailing Yacht
  • Length: 15.38 m
  • Year: 2014
  • Cabins: 4
  • Berths: 10
  • From $5008 to $7433 per week
Details Enquire
  • Berths: 10
  • Cabins: 4
  • Crew: Bareboat
  • Type: Sail
  • Length: 15.38 m (52' 2")
  • Year: 2014
From $5008 to $7433
per week

BOATBOOKINGS SAYS:
"Brand new Sun Odyssey 509 available in Gueadeloupe in 2014!"

Lagoon 400 - 3 Cabins - Tortola
Lagoon 400
    3 Cabins - Tortola
  • 3 Cabins Bareboat Catamaran
  • Length: 12.2 m
  • Year: 2010
  • Cabins: 3
  • Berths: 6
  • From $4100 to $6550 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 12.2 m (41' 8")
  • Year: 2010
From $4100 to $6550
per week

BOATBOOKINGS SAYS:
"This is a great spacious catamaran, built for both comfort and speed."

Lucia 40 - 3 Cabins - 2017 - Antigua
Lucia 40
    3 Cabins - 2017 - Antigua
  • 3 Cabins
  • Length: 11 m
  • Year: 2017
  • Cabins: 3
  • Berths: 8
  • Enquire for prices
Details Enquire
  • Berths: 8
  • Cabins: 3
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 11 m (37' 8")
  • Year: 2017
Enquire for prices

BOATBOOKINGS SAYS:
"An amazing new design from Fountaine Pajot which ensures comfort and happy sailors!"

Lagoon 400 S2 - 4 + 2 Cabins - 2016 - Antigua
Lagoon 400 S2
    4 + 2 Cabins - 2016 - Antigua
  • 4 + 2 Cabins
  • Length: 11 m
  • Year: 2016
  • Cabins: 4
  • Berths: 10
  • Enquire for prices
Details Enquire
  • Berths: 10
  • Cabins: 4
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 11 m (37' 8")
  • Year: 2016
Enquire for prices

BOATBOOKINGS SAYS:
"Brand new Lagoon 400 S2 available in Greece!"

Leopard 39 - 4 Cabins - Antigua
Leopard 39
    4 Cabins - Antigua
  • 4 Cabins Bareboat Catamaran
  • Length: 11.43 m
  • Year: 2012
  • Cabins: 3
  • Berths: 6
  • From $4495 to $7395 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 11.43 m (38' 3")
  • Year: 2012
From $4495 to $7395
per week

BOATBOOKINGS SAYS:
"Lovely, compact and brilliant to sail!"

Lavezzi 40 - 4 + 2 Cabins - St Martin
Lavezzi 40
    4 + 2 Cabins - St Martin
  • 4 + 2 Cabins Charter Catamaran
  • Length: 11.9 m
  • Year: 2007
  • Cabins: 6
  • Berths: 10
  • From $4295 to $6995 per week
Details Enquire
  • Berths: 10
  • Cabins: 6
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 11.9 m (40' 2")
  • Year: 2007
From $4295 to $6995
per week

Lipari 41 - 4 Cabins - 2012 - Guadeloupe
Lipari 41
    4 Cabins - 2012 - Guadeloupe
  • 4 Cabins Bareboat Catamaran
  • Length: 11.95 m
  • Year:
  • Cabins: 4
  • Berths: 10
  • Enquire for prices
Details Enquire
  • Berths: 10
  • Cabins: 4
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 11.95 m (40' 7")
  • Year:
Enquire for prices

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

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