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
- Riva Dolcevita 110 Luxury Crewed Motor Yacht
- Length: 33 m
- Year: 2019
- Cabins: 5
- Berths: 11
- From $115000 to $135000 per week
BOATBOOKINGS SAYS:
"Create cherished moments together, etched in your heart forever, as you savor a sumptuous Caribbean feast aboard NO SURRENDER."
- Dreamline 26 Luxury Crewed Motor Yacht
- Length: 26 m
- Year: 2019
- Cabins: 4
- Berths: 8
- From $69000 to $74000 per week
BOATBOOKINGS SAYS:
"Swap the rush for slow days in the BVI, as every day unfolds even better aboard THE PEDDLER!"
- Lagoon 50 Crewed Catamaran
- Length: 15 m
- Year: 2021
- Cabins: 4
- Berths: 8
- From $26000 to $29000 per week
BOATBOOKINGS SAYS:
"SCUBA DOO is the ultimate platform to explore the Virgin Islands, above and below the region's cerulean waters!"
- Fountaine Pajot Alegria 67 Crewed Catamaran
- Length: 20 m
- Year: 2023
- Cabins: 4
- Berths: 8
- From $40000 to $54000 per week
BOATBOOKINGS SAYS:
"Live your daydream aboard LOOMA, the brand new catamaran that promises an unforgettable adventure exploring the highlights of Sardinia!"
- Lagoon 620 Crewed Catamaran
- Length: 18 m
- Year: 2021
- Cabins: 4
- Berths: 8
- From $39000 to $42000 per week
BOATBOOKINGS SAYS:
"ASTROLABE is a luxurious and spacious choice for sailing the West Mediterranean and the Caribbean, and you won't be disappointed!"
- Mangusta Oceano 50 Luxury Crewed Motor Yacht
- Length: 49.99 m
- Year: 2022
- Cabins: 6
- Berths: 12
- From $295000 to $320000 per week
BOATBOOKINGS SAYS:
"Sleek and luxurious, embrace the suave as you venture through the Caribbean wonders on MAVERICK!"
- Cantiere delle Marche Darwin 106 Luxury Crewed Motor Yacht
- Length: 32 m
- Year: 2022
- Cabins: 6
- Berths: 12
- From $105000 to $120000 per week
BOATBOOKINGS SAYS:
"Lose the crowd, reset your tempo, the Caribbean Leewards unfold slowly aboard TROPA."
- Sunreef 80 Luxury Crewed Catamaran
- Length: 23 m
- Year: 2024
- Cabins: 5
- Berths: 12
- From $96000 to $120000 per week
BOATBOOKINGS SAYS:
"Explore the British Virgin Islands and the plethora of scenic destinations aboard MISCHIEVOUS!"
- Lagoon Sixty 5 Luxury Crewed Catamaran
- Length: 20.55 m
- Year: 2023
- Cabins: 4
- Berths: 8
- From €50000 to €55000 per week
BOATBOOKINGS SAYS:
"Explore calm coves and isles anew as REVE BLEU glides through the Caribbean and the West Mediterranean’s hue!"
- Fountaine Pajot Alegria 67 Luxury Crewed Catamaran
- Length: 20 m
- Year: 2022
- Cabins: 4
- Berths: 8
- From €56000 to €60000 per week
BOATBOOKINGS SAYS:
"SEMPER FIDELIS is always faithful to her mission of providing top-notch hospitality while exploring the Caribbean and the Bahamas."
