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
- Sunreef 74 Luxury Crewed Catamaran
- Length: 22 m
- Year: 2017
- Cabins: 4
- Berths: 9
- From €41800 to €47300 per week
BOATBOOKINGS SAYS:
"Striking, suave, and eye-catching, CALMAO is ready and raring to explore the Balearics and the Bahamas with you!"
- 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!"
- 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."
- Lagoon Sixty 5 Luxury Crewed Catamaran
- Length: 20.55 m
- Year: 2023
- Cabins: 4
- Berths: 8
- From €45000 to €50000 per week
BOATBOOKINGS SAYS:
"Explore calm coves and isles anew as REVE BLEU glides through the Caribbean and the West Mediterranean’s hue!"
- 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!"
- Numarine 37 XP Luxury Crewed Motor Yacht
- Length: 37.3 m
- Year: 2023
- Cabins: 5
- Berths: 10
- From $170000 per week
BOATBOOKINGS SAYS:
"Turn your world upside down and be amazed by the beauty of the Caribbean Leewards on EAU LA LA!"
- Fountaine Pajot Ipanema 58 Luxury Crewed Catamaran
- Length: 17 m
- Year: 2018 (2024 Refit)
- Cabins: 3
- Berths: 6
- From €25000 to €29000 per week
BOATBOOKINGS SAYS:
"You will surely enjoy your time soaking up the Sardinian and Caribbean sun while bathing in luxury on ARAOK!"
- Lagoon 45 Luxury Crewed Catamaran
- Length: 13.72 m
- Year: 2019
- Cabins: 3
- Berths: 6
- From $20000 to $28000 per week
BOATBOOKINGS SAYS:
"Stunning and immaculate catamaran with an experienced, fun crew perfect for exploring the crystal clear waters of the Caribbean!"
- Bali 4.8 Open Space Crewed Catamaran
- Length: 14 m
- Year: 2024
- Cabins: 4
- Berths: 8
- From $22500 to $28000 per week
BOATBOOKINGS SAYS:
"An extraordinary Caribbean journey awaits your family on BORROWED BOUNTY!"
- Lagoon 46 Crewed Catamaran
- Length: 14 m
- Year: 2020
- Cabins: 3
- Berths: 6
- From $20500 to $24000 per week
BOATBOOKINGS SAYS:
"Get lulled by the gentle rhythmic waves of the BVI waters on RITMO!"
- Dufour 48 Crewed Catamaran
- Length: 14 m
- Year: 2022
- Cabins: 4
- Berths: 8
- From $20000 to $24000 per week
BOATBOOKINGS SAYS:
"Built in 2022 SERENITY, a stunning catamaran model, offers an abundance of space inside and out."
- Bali 5.4 Crewed Catamaran
- Length: 16 m
- Year: 2025
- Cabins: 4
- Berths: 8
- From $31000 to $35000 per week
BOATBOOKINGS SAYS:
"Catch the breeze, chase the seas, and let ALLEGRA turn your BVI dreams into bliss."
- 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!"
- Lagoon 620 Luxury Crewed Catamaran
- Length: 18 m
- Year: 2016
- Cabins: 5
- Berths: 10
- From $42000 to $60000 per week
BOATBOOKINGS SAYS:
"Welcome aboard your cozy abode amidst the alluring Caribbean waters, the elegant SEAHOME!"
- Lagoon 620 Luxury Crewed Catamaran
- Length: 18 m
- Year: 2018
- Cabins: 4
- Berths: 8
- From $37500 to $42525 per week
BOATBOOKINGS SAYS:
"Pack your bags for an extraordinary adventure in the Caribbean on the luxurious and stylish BAGHEERA L620!"
- 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!"
- Lagoon Seventy 7 Luxury Crewed Catamaran
- Length: 23.28 m
- Year: 2021 (2024 Refit)
- Cabins: 4
- Berths: 8
- From €77000 per week
BOATBOOKINGS SAYS:
"Experience the serenity of nature amidst the Caribbean Leewards aboard the luxurious catamaran CAT TUA!"
- Johnson 87 Luxury Crewed Motor Yacht
- Length: 26 m
- Year: 2006
- Cabins: 4
- Berths: 8
- From $54000 to $59000 per week
BOATBOOKINGS SAYS:
"Let each golden day unfold on Bahamas tides aboard SOUTHERN BELLE, where comfort and adventure collide."
- Horizon P130 Luxury Crewed Motor Yacht
- Length: 41 m
- Year: 2010 (2024 Refit)
- Cabins: 6
- Berths: 12
- From $140000 to $165000 per week
BOATBOOKINGS SAYS:
"Stay adventurous and salty on the Bahamian waters aboard this luxurious Horizon yacht!"
- Mangusta Oceano 43 Luxury Crewed Motor Yacht
- Length: 43 m
- Year: 2021
- Cabins: 5
- Berths: 10
- From $220000 to $240000 per week
BOATBOOKINGS SAYS:
"Pure joy awaits in the French Riviera while cruising in luxury and style on TOY!"
- Vitters 43m Luxury Crewed Sailing Yacht
- Length: 43 m
- Year: 2004 (2012 Refit)
- Cabins: 5
- Berths: 10
- From €98000 to €112000 per week
BOATBOOKINGS SAYS:
"Large array of water toys and impressive number of guests with up to 7 crew - she comes highly recommended."
- Bering 145 Luxury Crewed Motor Yacht
- Length: 44.2 m
- Year: 2023
- Cabins: 6
- Berths: 12
- From €225000 to €275000 per week
BOATBOOKINGS SAYS:
"From sunrise hues to midnight views, the French Riviera feels better aboard HEEUS!"
- 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."
- Trinity 164 Luxury Crewed Motor Yacht
- Length: 50 m
- Year: 2009
- Cabins: 5
- Berths: 12
- From $230000 to $250000 per week
BOATBOOKINGS SAYS:
"Extraordinary Luxury Yacht with palatial interior and an abundance of special features."
- Lagoon 450 Luxury Crewed Catamaran
- Length: 13.7 m
- Year: 2014
- Cabins: 3
- Berths: 6
- From $16500 to $18500 per week
BOATBOOKINGS SAYS:
"GREAT ADVENTURE is an immaculate catamaran that is perfect for people who love water sports and scuba diving!"
- Trinity 161 Luxury Crewed Motor Yacht
- Length: 49 m
- Year: 2007 (2024 Refit)
- Cabins: 5
- Berths: 12
- From €225000 per week
BOATBOOKINGS SAYS:
"From reef-rimmed bays to champagne-drenched sunsets, DIRT POOR is the Bahamas escape you’ll never want to leave!"
- Lagoon 52 Crewed Catamaran
- Length: 15 m
- Year: 2019
- Cabins: 6
- Berths: 12
- From €9750 to €15600 per week
BOATBOOKINGS SAYS:
"DUGONGO II is an intimate crewed catamaran ideal for a family charter in the Caribbean!"
- Robertson and Caine Leopard 50 Crewed Catamaran
- Length: 15.4 m
- Year: 2024
- Cabins: 3
- Berths: 6
- From $21000 to $26000 per week
BOATBOOKINGS SAYS:
"Lift your mood by embarking on a Caribbean cruise on BOATOX!"
