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 Sanya 57 Luxury Crewed Catamaran
- Length: 17.98 m
- Year: 2015
- Cabins: 5
- Berths: 10
- From $34500 to $40500 per week
BOATBOOKINGS SAYS:
"Come to life on board ALIVE in the spectacular British Virgin Islands!"
- Lagoon 620 Luxury Crewed Catamaran
- Length: 18.89 m
- Year: 2017
- Cabins: 3
- Berths: 6
- From $42000 to $46000 per week
BOATBOOKINGS SAYS:
"LE REVE is the leading 3 cabin crewed catamaran in the BVI with an amazing crew. You will not be disappointed!"
- Lagoon 630 Luxury Crewed Power Catamaran
- Length: 64 m
- Year: 2018
- Cabins: 4
- Berths: 8
- From 0 to 0 per week
BOATBOOKINGS SAYS:
"MARE BLU is a luxurious alternative to a sailing catamaran, offering a superb charter around the Caribbean islands."
- Fountaine Pajot Ipanema 58 Crewed Catamaran
- Length: 18.28 m
- Year: 2018
- Cabins: 5
- Berths: 8
- From $34200 to $43092 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 $45300 to $52000 per week
BOATBOOKINGS SAYS:
"Zingara never ceases to please those looking for quality sailing and deluxe comfort!"
- Christensen 120 Luxury Crewed Motor Yacht
- Length: 36 m
- Year: 1995
- Cabins: 4
- Berths: 8
- From $65000 to $65000 per week
BOATBOOKINGS SAYS:
"Step onboard CHERISH II for an epic charter experience in the Bahamas, Florida and the Caribbean Virgin Islands."
- 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!"
- Fountaine Pajot Ipanema 58 Luxury Crewed Catamaran
- Length: 18 m
- Year: 2015
- Cabins: 4
- Berths: 8
- From $26000 to $30000 per week
BOATBOOKINGS SAYS:
"This stunning crewed catamaran is ideal for a luxurious charter holiday around the Caribbean with a fantastic Chef!"
- Lagoon 620 Luxury Crewed Catamaran
- Length: 18.9 m
- Year: 2014
- Cabins: 5
- Berths: 10
- From $33000 to $40000 per week
BOATBOOKINGS SAYS:
"She has sophisticated touches throughout with a dedicated crew, perfect for your next family yacht charter."
- Lagoon 620 Crewed Catamaran
- Length: 18.9 m
- Year: 2010
- Cabins: 4
- Berths: 8
- From €23000 to €25000 per week
BOATBOOKINGS SAYS:
"One of the best crewed Catamarans on the French Riviera!"
- Sunreef 70 Luxury Crewed Catamaran
- Length: 21.34 m
- Year: 2011
- Cabins: 6
- Berths: 12
- From €32000 per week
BOATBOOKINGS SAYS:
"Fun and relaxed atmosphere, absolutely delicious food, ideal family charter; Muse comes highly recommended by the Managing Director who had lunch aboard in Antigua."
- Westport 130 Luxury Crewed Motor Yacht
- Length: 39.62 m
- Year: 2014
- Cabins: 5
- Berths: 10
- From $125000 to $140000 per week
BOATBOOKINGS SAYS:
"Elegant and understated luxury awaits onboard PIPE DREAM. Offering unrivalled amenities, accommodation and entertainment areas - it is no wonder she is the leading 130 Westport cruising the Bahamas and Caribbean."
- Lagoon 67 Crewed Power Catamaran
- Length: 20 m
- Year: 2022
- Cabins: 3
- Berths: 6
- From $59000 to $65000 per week
BOATBOOKINGS SAYS:
"Step aboard this stand out crewed catamaran and begin making unforgettable memories in the Virgin Islands with the amazing crew who were awarded Best Crew at the 2022 USVI Yacht Show!"
- San Lorenzo 46m Luxury Crewed Motor Yacht
- Length: 46 m
- Year: 2015
- Cabins: 5
- Berths: 12
- From €225000 per week
BOATBOOKINGS SAYS:
"This exceptional superyacht radiates magnificence, stunning inside and out."
- Day Charter and Week Long Charter Luxury Crewed Catamaran
- Length: 57 m
- Year: 1995
- Cabins: 4
- Berths: 4
- From $3500 to $12990 per day
BOATBOOKINGS SAYS:
"Fantastic day charter, with the option of chartering for a week in the unrivalled BVI!"
- 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 beautifully eye-catching, CALMAO is ready and raring to explore the Bahamas and Balearics."
- Benetti 37m Luxury Crewed Motor Yacht
- Length: 36 m
- Year: 2009
- Cabins: 5
- Berths: 10
- From $125000 to $135000 per week
BOATBOOKINGS SAYS:
"PAPAITO is a luxury motor yacht available for charter in the Bahamas!"
- Fountaine Pajot Ipanema 58 Luxury Crewed Catamaran
- Length: 17.8 m
- Year: 2018
- Cabins: 3
- Berths: 6
- From €25000 to €29000 per week
BOATBOOKINGS SAYS:
"“They LOVED their charter and especially the CREW.”"
- Swan 82 Luxury Crewed Sailing Yacht
- Length: 24.9 m
- Year: 2012
- Cabins: 3
- Berths: 6
- From $39500 to $42500 per week
BOATBOOKINGS SAYS:
"Built for high performance sailing, whilst offering elegance and opulence both above and below deck!"
- Lagoon 45 Luxury Crewed Catamaran
- Length: 13.72 m
- Year: 2019
- Cabins: 3
- Berths: 6
- From $20000 to $23500 per week
BOATBOOKINGS SAYS:
"Stunning and immaculate catamaran with an experienced, fun crew perfect for exploring the crystal clear waters of the Caribbean!"
- Lagoon 50 Luxury Crewed Catamaran
- Length: 14.75 m
- Year: 2020
- Cabins: 4
- Berths: 8
- From $25000 to $28000 per week
BOATBOOKINGS SAYS:
"Step aboard onto stunning luxury crewed catamaran, KARMA, and set sail around the beautiful Virgin Islands!"
- Lagoon 620 Crewed Catamaran
- Length: 18 m
- Year: 2021
- Cabins: 4
- Berths: 8
- From $39000 to $46000 per week
BOATBOOKINGS SAYS:
"BREIZ-ILE is a luxurious and spacious choice for sailing the Caribbean; you won't be disappointed!"
- Sunreef Supreme 68 Luxury Crewed Catamaran
- Length: 20.73 m
- Year: 2017
- Cabins: 5
- Berths: 10
- From €38000 to €45000 per week
BOATBOOKINGS SAYS:
"This state-of-the-art Catamaran is an indisputable game changer. MAYRILOU space and beautiful decor will offer guests uninterrupted peace of mind and comfort."
- 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."
- 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."
- Feadship 50m Luxury Crewed Motor Yacht
- Length: 49.5 m
- Year: 1986
- Cabins: 7
- Berths: 13
- From $155000 to $175000 per week
BOATBOOKINGS SAYS:
"With her impressive history, modern refit, and state-of-the-art features, you can live a glamorous and luxurious lifestyle aboard HIGHLANDER this season."
- Matrix Silhouette 76 Luxury Crewed Catamaran
- Length: 23.16 m
- Year: 2013
- Cabins: 6
- Berths: 12
- From $54950 to $64950 per week
BOATBOOKINGS SAYS:
"This is a unique, huge and extremely successful Catamaran for 12 guests - a Boatbookings favourite in the BVI!"
- Sunreef 70 Luxury Crewed Catamaran
- Length: 21 m
- Year: 2021
- Cabins: 4
- Berths: 8
- From €59000 to €69000 per week
BOATBOOKINGS SAYS:
"ANIMA is a modern luxury catamaran thaat signals the future of yachting with her zero emissions and sustainable design!"
- Merritt 86 Fishing Boat
- Length: 26.21 m
- Year: 2017
- Cabins: 5
- Berths: 10
- From $70000 to $70000 per week
BOATBOOKINGS SAYS:
"Fishing has never been so luxurious than onboard REEL TIGHT."
- Benetti 44m Luxury Crewed Motor Yacht
- Length: 44 m
- Year: 2010
- Cabins: 5
- Berths: 10
- From $159000 to $169000 per week
BOATBOOKINGS SAYS:
"ARSANA is an ideal motor yacht for chartering with family or friends."
