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

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
  • 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"

Lagoon 450 Luxe
    2016 - 4 + 2 Cabins - Antigua
  • 2016 Bareboat 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
  • 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!"

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
  • 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."

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
  • 4 + 2 Cabins Bareboat 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

BEING NAUTI
  • Bareboat Catamaran
  • Length: 11.95 m
  • Year: 2013
  • Cabins: 4
  • Berths: 8
  • From $6800 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 11.95 m (40' 7")
  • Year: 2013
From $6800
per week

BOATBOOKINGS SAYS:
"A beautiful ocean going catamaran."

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 400 S2
    4 Cabins - British Virgin Islands - Tortola - St Maarten
  • 4 Cabins Bareboat Catamaran
  • Length: 11.98 m
  • Year: 2013
  • Cabins: 4
  • Berths: 8
  • From $5000 to $7400 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 11.98 m (40' 10")
  • Year: 2013
From $5000 to $7400
per week

BOATBOOKINGS SAYS:
"Spacious, light, and airy with plenty of headroom."

CHIANTI
  • Bareboat Sailing Yacht
  • Length: 12.38 m
  • Year: 2014
  • Cabins: 3
  • Berths: 8
  • Enquire for prices
Details Enquire
  • Berths: 8
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 12.38 m (42' 2")
  • Year: 2014
Enquire for prices

Lagoon 420
    4 Cabins - British Virgin Islands - Tortola
  • 4 Cabins Bareboat Catamaran
  • Length: 12.61 m
  • Year: 2008
  • Cabins: 4
  • Berths: 8
  • From $5200 to $7900 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 12.61 m (42' 1")
  • Year: 2008
From $5200 to $7900
per week

BOATBOOKINGS SAYS:
"Designed for luxury and comfort."

HAWKING
  • Bareboat Sailing Yacht
  • Length: 12.9 m
  • Year: 2012
  • Cabins: 3
  • Berths: 8
  • Enquire for prices
Details Enquire
  • Berths: 8
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 12.9 m (43' 6")
  • Year: 2012
Enquire for prices

CORAZON VIEW 1 REVIEW 
CORAZON
  • Bareboat Catamaran
  • Length: 13.1 m
  • Year: 2019
  • Cabins: 4
  • Berths: 0
  • From €4500 to €9915 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 0
  • Cabins: 4
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 13.1 m (44' 2")
  • Year: 2019
VIEW 1 REVIEW
From €4500 to €9915
per week

Lagoon 440 (2009)
    4 + 2 Cabins - British Virgin Islands - Tortola - St Maarten
  • 4 + 2 Cabins Bareboat Catamaran
  • Length: 13.65 m
  • Year:
  • Cabins: 6
  • Berths: 12
  • From $7200 to $9400 per week
Details Enquire
  • Berths: 12
  • Cabins: 6
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 13.65 m (46' 9")
  • Year:
From $7200 to $9400
per week

BOATBOOKINGS SAYS:
"Seaworthy, elegant, powerful, and fully loaded with options."

Lagoon 450
    4 Cabins - British Virgin Islands - Tortola - St Maarten
  • 4 Cabins Bareboat Catamaran
  • Length: 13.74 m
  • Year: 2012
  • Cabins: 4
  • Berths: 8
  • From $7700 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 13.74 m (46' 6")
  • Year: 2012
From $7700
per week

BOATBOOKINGS SAYS:
"Reliable, innovative, fast and easy to handle."

CATCH THE CAT
  • Bareboat Catamaran
  • Length: 13.96 m
  • Year: 2012
  • Cabins: 6
  • Berths: 8
  • From $7700 per week
Details Enquire
  • Berths: 8
  • Cabins: 6
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 13.96 m (47' 4")
  • Year: 2012
From $7700
per week

BOATBOOKINGS SAYS:
"Well equipped and perfect for long distance cruising, this is the ultimate catamaran."

KILIMANDJARO
  • Bareboat Catamaran
  • Length: 14.02 m
  • Year: 2012
  • Cabins: 6
  • Berths: 10
  • From $3975 to $4635 per week
Details Enquire
  • Berths: 10
  • Cabins: 6
  • Crew: Bareboat
  • Type: Catamaran
  • Length: 14.02 m (47' 10")
  • Year: 2012
From $3975 to $4635
per week

ISLE DANCE II
  • Bareboat Sailing Yacht
  • Length: 14.97 m
  • Year: 2008
  • Cabins: 5
  • Berths: 10
  • From $4500 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Bareboat
  • Type: Sail
  • Length: 14.97 m (50' 9")
  • Year: 2008
From $4500
per week

BOATBOOKINGS SAYS:
"A spacious yacht, perfect for for friends and families."

Sun Odyssey 509
    5 Cabins - British Virgin Islands - St Maarten - Tortola - Trinidad
  • 5 Cabins Bareboat Sailing Yacht
  • Length: 15.38 m
  • Year: 2013
  • Cabins: 5
  • Berths: 10
  • From €3365 to €7850 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Bareboat
  • Type: Sail
  • Length: 15.38 m (52' 2")
  • Year: 2013
From €3365 to €7850
per week

FRENCH MAID
  • Bareboat Sailing Yacht
  • Length: 15.43 m
  • Year: 2012
  • Cabins: 3
  • Berths: 6
  • From $5500 to $8000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 15.43 m (52' 7")
  • Year: 2012
From $5500 to $8000
per week

BOATBOOKINGS SAYS:
"Fast, exceptional seaworthiness and unparalled comfort, a joy to sail."

XERES
  • Bareboat Sailing Yacht
  • Length: 15.38 m
  • Year: 2014
  • Cabins: 7
  • Berths: 10
  • From €3365 to €7850 per week
Details Enquire
  • Berths: 10
  • Cabins: 7
  • Crew: Bareboat
  • Type: Sail
  • Length: 15.38 m (52' 2")
  • Year: 2014
From €3365 to €7850
per week

Bavaria 40
    3 Cabins - Antigua
  • 3 Cabins Bareboat Sailing Yacht
  • Length: 40 m
  • Year: 2010
  • Cabins: 3
  • Berths: 6
  • From $3195 to $4295 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Bareboat
  • Type: Sail
  • Length: 40 m (136' 4")
  • Year: 2010
From $3195 to $4295
per week

BOATBOOKINGS SAYS:
"Wonderful sailing performance!"

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