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
- Fountaine Pajot Alegria 67 Crewed Catamaran
- Length: 20 m
- Year: 2021
- Cabins: 4
- Berths: 8
- From €45000 to €50000 per week
BOATBOOKINGS SAYS:
"Be inspired by the Jacuzzi and enchanting vistas of Croatia or the Caribbean on INSPIRANTE!"
- Christensen 162 Luxury Crewed Motor Yacht
- Length: 49.37 m
- Year: 2011 (refit 2020)
- Cabins: 6
- Berths: 8
- From $230000 to $230000 per week
BOATBOOKINGS SAYS:
"Step onboard REMEMBER WHEN and enjoy the Bahamas and Caribbean in unrivalled luxury this year."
- Fountaine Pajot Ipanema 58 Crewed Catamaran
- Length: 18.28 m
- Year: 2018
- Cabins: 5
- Berths: 8
- From $34200 to $39900 per week
BOATBOOKINGS SAYS:
"Outstanding is the word for this crewed catamaran - just have a look at the reviews from clients!"
- Matrix Silhouette 76 Luxury Crewed Catamaran
- Length: 22.34 m
- Year: 2006 (2017 Refit)
- Cabins: 5
- Berths: 10
- From $49800 to $57500 per week
BOATBOOKINGS SAYS:
"Zingara never ceases to please those looking for quality sailing and deluxe comfort!"
- Sunreef Eco 80 Luxury Crewed Catamaran
- Length: 24 m
- Year: 2024
- Cabins: 4
- Berths: 8
- From $95000 to $99000 per week
BOATBOOKINGS SAYS:
"Sail between worlds of beauty aboard THE IDLER, basking in Sardinia’s golden summer and Caribbean bliss when winter arrives!"
- Bali 5.4 Luxury Crewed Catamaran
- Length: 16 m
- Year: 2024
- Cabins: 5
- Berths: 10
- From $0 to $38000 per week
BOATBOOKINGS SAYS:
"Find peace of mind aboard MASTERMIND II, where the Leewards shine and the sea stays blue."
- Heesen 55m Luxury Crewed Motor Yacht
- Length: 54 m
- Year: 2012
- Cabins: 6
- Berths: 12
- From $320000 to $350000 per week
BOATBOOKINGS SAYS:
"Let SOUTH set the pace in a Bahamas embrace, where sunlit decks and turquoise water put joy in its place!"
- Bali 5.4 Crewed Catamaran
- Length: 16 m
- Year: 2024
- Cabins: 4
- Berths: 8
- From $31000 to $35000 per week
BOATBOOKINGS SAYS:
"Take in the lovely vistas of the British Virgin Islands on award-winning catamaran LA VIE EST BELLE!"
- Bali 4.6 Crewed Catamaran
- Length: 14 m
- Year: 2023
- Cabins: 4
- Berths: 8
- From $23000 to $27000 per week
BOATBOOKINGS SAYS:
"Feel the sun's kiss and appreciate the immaculate beauty of the British Virgin Islands on APRICITY!"
- Bali 4.8 Crewed Catamaran
- Length: 14 m
- Year: 2022
- Cabins: 4
- Berths: 8
- From $24000 to $28000 per week
BOATBOOKINGS SAYS:
"Listen to the melodic orchestra of the gentle Caribbean waves and feel the warm sea breeze, providing relaxing comfort while you're aboard HARMONY!"
- Xquisite X5 Crewed Catamaran
- Length: 15.24 m
- Year: 2022
- Cabins: 2
- Berths: 4
- From $22700 to $24000 per week
BOATBOOKINGS SAYS:
"Don't miss out on the fun with your friends in the Bahamian Islands on WILD RUMPUS!"
- Bali 5.4 Luxury Crewed Catamaran
- Length: 17 m
- Year: 2023
- Cabins: 5
- Berths: 10
- From $26000 to $32000 per week
BOATBOOKINGS SAYS:
"Let the stunning Bali catamaran MOTEK be your partner in an exhilarating Bahamian or Caribbean exploration!"
- Bali 5.4 Crewed Catamaran
- Length: 16 m
- Year: 2023
- Cabins: 5
- Berths: 10
- From $30500 to $35000 per week
BOATBOOKINGS SAYS:
"HYDROTHERAPY is a great choice for friends and family seeking to discover the BVI in utmost serenity!"
- Sunreef 80 Luxury Crewed Catamaran
- Length: 23.99 m
- Year: 2020 (2023 Refit)
- Cabins: 4
- Berths: 8
- From $60000 to $80000 per week
BOATBOOKINGS SAYS:
"SEACLUSION is one of the top catamarans chartering the Caribbean and has won the Best Yacht in the 2022 USVI Yacht Show!"
- Lagoon 620 Crewed Catamaran
- Length: 18 m
- Year: 2016 (2024 Refit)
- Cabins: 4
- Berths: 8
- From $48000 to $52000 per week
BOATBOOKINGS SAYS:
"ANDROMEDA is the perfect vessel to uncover the beauty of the Bahamas befitting of her name!"
- Lagoon 67 Crewed Power Catamaran
- Length: 20 m
- Year: 2022
- Cabins: 4
- Berths: 8
- From $54000 to $60000 per week
BOATBOOKINGS SAYS:
"Step aboard this stand-out crewed catamaran and begin making unforgettable memories in the Caribbean Virgin Islands with the amazing crew who were awarded Best Crew at the 2022 USVI Yacht Show!"
- Princess 82 Luxury Crewed Motor Yacht
- Length: 24 m
- Year: 2018 (2023 Refit)
- Cabins: 4
- Berths: 8
- From $35000 to $57600 per week
BOATBOOKINGS SAYS:
"You will surely be looked after by a passionate crew as you cruise the enchanting Caribbean islands on SORANA II."
- Lagoon 620 Crewed Catamaran
- Length: 18 m
- Year: 2019 (2022 Refit)
- Cabins: 4
- Berths: 8
- From $39500 to $42500 per week
BOATBOOKINGS SAYS:
"Feel the fresh Caribbean breeze aboard the DRAGONFLY on your British Virgin Islands cruise."
- Sunreef 80 Luxury Crewed Catamaran
- Length: 24 m
- Year: 2022
- Cabins: 4
- Berths: 8
- From $92000 to $100000 per week
BOATBOOKINGS SAYS:
"Enjoy unparalleled proportions, luxury, and comfort as you island-hop with Captain Jonathan and his vibrant crew on one of the finest Sunreef crewed catamarans in the Caribbean BVI and the Bahamas!"
- Sanlorenzo SD90 Luxury Crewed Motor Yacht
- Length: 27.43 m
- Year: 2023
- Cabins: 4
- Berths: 9
- From $90000 to $99000 per week
BOATBOOKINGS SAYS:
"Drift from harbor lights to turquoise sights across the Leewards aboard LAILA!"
- Benetti 121 Luxury Crewed Motor Yacht
- Length: 36.9 m
- Year: 2011 (2022 Refit)
- Cabins: 5
- Berths: 10
- From $110000 to $120000 per week
BOATBOOKINGS SAYS:
"Grace the shores of the Caribbean Leewards luxurious comfort on ALLORA!"
- Lagoon 65 Luxury Crewed Catamaran
- Length: 19 m
- Year: 2021
- Cabins: 5
- Berths: 10
- From $59000 to $72000 per week
BOATBOOKINGS SAYS:
"A fantastic award-winning crewed catamaran for charters around the Virgin Islands!"
- Lagoon Seventy 7 Luxury Crewed Catamaran
- Length: 23 m
- Year: 2020
- Cabins: 4
- Berths: 8
- From $77000 to $80000 per week
BOATBOOKINGS SAYS:
"One of the Lagoon Seventy 7s chartering the Caribbean Virgin Islands, MARIAH PRINCESS III is the ultimate yacht for a blissful and adventurous charter experience."
- Azimut Grande 27m Luxury Crewed Motor Yacht
- Length: 26 m
- Year: 2022
- Cabins: 5
- Berths: 8
- From $80000 to $90000 per week
BOATBOOKINGS SAYS:
"Let SEA OWL guide your days through the British Virgin Islands, where calm cruising and sharp insight lead every island moment."
- Sunseeker 95 Luxury Crewed Motor Yacht
- Length: 28 m
- Year: 2024
- Cabins: 5
- Berths: 10
- From $95000 to $115000 per week
BOATBOOKINGS SAYS:
"Experience exclusivity on ACCIDENTAL SUCCESS II while exploring the Caribbean Leewards your round!"
- Burger 144 Luxury Crewed Motor Yacht
- Length: 43 m
- Year: 2006 (2021 Refit)
- Cabins: 7
- Berths: 12
- From $175000 to $195000 per week
BOATBOOKINGS SAYS:
"CROSSED SABRE has the volume of a much larger motor yacht, ideal for charter in the Bahamas and the Caribbean."
- Moonen 122 Martinique Luxury Crewed Motor Yacht
- Length: 37.39 m
- Year: 2025
- Cabins: 5
- Berths: 10
- From $168000 to $182000 per week
BOATBOOKINGS SAYS:
"Where waves ignite, and stars delight, AD ASTRA cruises through the Bahamian and Caribbean nights!"
- Palmer Johnson 150 Luxury Crewed Motor Yacht
- Length: 45.7 m
- Year: 2009 (2024 Refit)
- Cabins: 5
- Berths: 10
- From $145000 to $160000 per week
BOATBOOKINGS SAYS:
"Be seen aboard the stylish NORMA JEAN, where Bahamas blues create a showstopping scene!"
- Sanlorenzo SD96 Luxury Crewed Motor Yacht
- Length: 28.96 m
- Year: 2023
- Cabins: 5
- Berths: 10
- From $90000 to $105000 per week
BOATBOOKINGS SAYS:
"When chic escapes and blue seas align, St Barths to St Martin shine aboard ADIOS!"
- Benetti Motopanfilo 37m Luxury Crewed Motor Yacht
- Length: 36.91 m
- Year: 2022
- Cabins: 5
- Berths: 10
- From $160000 to $175000 per week
BOATBOOKINGS SAYS:
"KOJU was one of our standout yachts from FLIBS 2023; you will be dazzled by Captain Nick and his crew's dedication to delivering the ultimate Bahamas experience!"
