Luxury Yacht Charter in the Leeward Islands
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!
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
- 5 Cabins Bareboat Sailing Yacht
- Length: 14.6 m
- Year: 2013
- Cabins: 5
- Berths: 12
- 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!"
- 4 Cabins Bareboat Catamaran
- Length: 13.6 m
- Year: 2017
- Cabins: 4
- Berths: 8
- From $3800 to $9785 per week
BOATBOOKINGS SAYS:
"Fantastically modern, this new for 2017 Bali catamaran is stunning"
- 4 + 2 Cabins Bareboat Catamaran
- Length: 12.57 m
- Year:
- Cabins: 6
- Berths: 12
- From $4968 to $12414 per week
- 2016 Bareboat Catamaran
- Length: 14.02 m
- Year: 2016
- Cabins: 6
- Berths: 10
- From $7500 to $10000 per week
BOATBOOKINGS SAYS:
"One of the newest and most modern catamarans on the water!"
- 4 Cabins Bareboat Sailing Yacht
- Length: 14.05 m
- Year: 2013
- Cabins: 4
- Berths: 8
- From $4000 to $6000 per week
BOATBOOKINGS SAYS:
"A brand new vessel perfectly adapted to sail the BVIs!"
- 5 Cabins Bareboat Sailing Yacht
- Length: 15.38 m
- Year: 2014
- Cabins: 4
- Berths: 10
- From $5008 to $7433 per week
BOATBOOKINGS SAYS:
"Brand new Sun Odyssey 509 available in Gueadeloupe in 2014!"
- 3 Cabins Bareboat Catamaran
- Length: 12.2 m
- Year: 2010
- Cabins: 3
- Berths: 6
- From $4100 to $6550 per week
BOATBOOKINGS SAYS:
"This is a great spacious catamaran, built for both comfort and speed."
- 4 Cabins Bareboat Catamaran
- Length: 11.43 m
- Year: 2012
- Cabins: 3
- Berths: 6
- From $4495 to $7395 per week
BOATBOOKINGS SAYS:
"Lovely, compact and brilliant to sail!"
- Bareboat Catamaran
- Length: 11.95 m
- Year: 2013
- Cabins: 4
- Berths: 8
- From $6800 per week
BOATBOOKINGS SAYS:
"A beautiful ocean going catamaran."
- Bareboat Catamaran
- Length: 11.95 m
- Year: 2013
- Cabins: 4
- Berths: 8
- From $3050 to $7300 per week
BOATBOOKINGS SAYS:
"Her sleek lines and modern interior make this a brilliant choice for chartering."
- 4 Cabins Bareboat Catamaran
- Length: 11.98 m
- Year: 2013
- Cabins: 4
- Berths: 8
- From $5000 to $7400 per week
BOATBOOKINGS SAYS:
"Spacious, light, and airy with plenty of headroom."
- 4 Cabins Bareboat Catamaran
- Length: 12.61 m
- Year: 2008
- Cabins: 4
- Berths: 8
- From $5200 to $7900 per week
BOATBOOKINGS SAYS:
"Designed for luxury and comfort."
- Bareboat Catamaran
- Length: 13.1 m
- Year: 2019
- Cabins: 4
- Berths: 0
- From €4500 to €9915 per week
- 4 + 2 Cabins Bareboat Catamaran
- Length: 13.65 m
- Year:
- Cabins: 6
- Berths: 12
- From $7200 to $9400 per week
BOATBOOKINGS SAYS:
"Seaworthy, elegant, powerful, and fully loaded with options."
- 4 Cabins Bareboat Catamaran
- Length: 13.74 m
- Year: 2012
- Cabins: 4
- Berths: 8
- From $7700 per week
BOATBOOKINGS SAYS:
"Reliable, innovative, fast and easy to handle."
- Bareboat Catamaran
- Length: 13.96 m
- Year: 2012
- Cabins: 6
- Berths: 8
- From $7700 per week
BOATBOOKINGS SAYS:
"Well equipped and perfect for long distance cruising, this is the ultimate catamaran."
- Bareboat Sailing Yacht
- Length: 14.97 m
- Year: 2008
- Cabins: 5
- Berths: 10
- From $4500 per week
BOATBOOKINGS SAYS:
"A spacious yacht, perfect for for friends and families."
- 5 Cabins Bareboat Sailing Yacht
- Length: 15.38 m
- Year: 2013
- Cabins: 5
- Berths: 10
- From €3365 to €7850 per week
- Bareboat Sailing Yacht
- Length: 15.43 m
- Year: 2012
- Cabins: 3
- Berths: 6
- From $5500 to $8000 per week
BOATBOOKINGS SAYS:
"Fast, exceptional seaworthiness and unparalled comfort, a joy to sail."
- Bareboat Sailing Yacht
- Length: 15.38 m
- Year: 2014
- Cabins: 7
- Berths: 10
- From €3365 to €7850 per week
- 3 Cabins Bareboat Sailing Yacht
- Length: 40 m
- Year: 2010
- Cabins: 3
- Berths: 6
- From $3195 to $4295 per week
BOATBOOKINGS SAYS:
"Wonderful sailing performance!"
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