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
- Lagoon Sixty 5 Luxury Crewed Catamaran
- Length: 20.42 m
- Year: 2023
- Cabins: 4
- Berths: 8
- From €50000 to €72000 per week
BOATBOOKINGS SAYS:
"Nightly rave parties await onboard REVE BLEU as you explore the South of France and the Caribbean!"
- 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."
- Robertson and Caine 43 Crewed Catamaran
- Length: 13.4 m
- Year: 2000 (2022 Refit)
- Cabins: 3
- Berths: 6
- From $12500 to $15500 per week
BOATBOOKINGS SAYS:
"Say yes to a memorable Caribbean cruise on NOVA!"
- Privilege Alliaura Marine Group 58 Crewed Motor Yacht
- Length: 17 m
- Year: 2004
- Cabins: 4
- Berths: 8
- From $23000 to $27000 per week
BOATBOOKINGS SAYS:
"LADY MARIGOT is your gateway to unforgettable adventures in the Caribbean year-round!"
- Sunreef Supreme 68 Power Catamaran
- Length: 22 m
- Year: 2024
- Cabins: 4
- Berths: 8
- From $69000 to $75000 per week
BOATBOOKINGS SAYS:
"Indulge in an everyday feast while cruising the BVI on MARIA THERESE!"
- Sunreef Eco 80 Luxury Crewed Catamaran
- Length: 24 m
- Year: 2024
- Cabins: 4
- Berths: 8
- From $90000 to $99000 per week
BOATBOOKINGS SAYS:
"Discover opulent living at sea on THE IDLER in the Caribbean this summer!"
- Riva Argo 90 Crewed Motor Yacht
- Length: 28.49 m
- Year: 2020
- Cabins: 4
- Berths: 8
- From $85000 to $95000 per week
BOATBOOKINGS SAYS:
"Say yes to non-stop adventures in the Grenadines on NOI!"
- Trident 40m Luxury Crewed Motor Yacht
- Length: 40.23 m
- Year: 1999 (2023 Refit)
- Cabins: 5
- Berths: 10
- From $128000 to $148000 per week
BOATBOOKINGS SAYS:
"Fill your heart with joy as you cruise St. Martin and St. Barths on PACKAGE DEAL!"
- YYacht Y7 Crewed Sailing Yacht
- Length: 21.86 m
- Year: 2024
- Cabins: 3
- Berths: 6
- From €24000 to €28500 per week
BOATBOOKINGS SAYS:
"YUME, together with her outstanding crew, will surely amaze you and your group as you gasp with awe while witnessing the Balearics' highlights!"
- Benetti Classic 120 Luxury Crewed Motor Yacht
- Length: 36 m
- Year: 2008
- Cabins: 5
- Berths: 10
- From $95000 to $105000 per week
BOATBOOKINGS SAYS:
"Cease each day and live every moment in your Bahamas cruise on ARTHUR'S WAY."
- 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 $47300 to $54000 per week
BOATBOOKINGS SAYS:
"Zingara never ceases to please those looking for quality sailing and deluxe comfort!"
- Burger 144 Luxury Crewed Motor Yacht
- Length: 43.89 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."
- Lagoon Seventy 7 Luxury Crewed Catamaran
- Length: 23 m
- Year: 2022
- Cabins: 5
- Berths: 10
- From €60000 to €74000 per week
BOATBOOKINGS SAYS:
"Experience the ultimate yacht charter in Amalfi Coast with our brand new SYLENE, your luxurious sanctuary on the sea."
- 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!"
- Robertson and Caine 42 Crewed Catamaran
- Length: 13.11 m
- Year: 2011
- Cabins: 4
- Berths: 7
- From $13950 to $16850 per week
BOATBOOKINGS SAYS:
"Dance or get lulled into a trance on GROOVY with her excellent crew who will give you a fantastic charter experience!"
- Bali 4.8 Crewed Catamaran
- Length: 14 m
- Year: 2024
- Cabins: 3
- Berths: 6
- From $22500 to $24500 per week
BOATBOOKINGS SAYS:
"Bask and relax in the sunlight with your favorite cocktail blend as you cruise the British Virgin Islands on ALORA!"
- Leopard 46 Crewed Catamaran
- Length: 14 m
- Year: 2012
- Cabins: 3
- Berths: 7
- From $16000 to $17500 per week
BOATBOOKINGS SAYS:
"Your camera will never rest from the spectacular sceneries of the Caribbean on SARA!"
- Robertson and Caine Leopard 50 Crewed Catamaran
- Length: 15 m
- Year: 2020
- Cabins: 3
- Berths: 6
- From $19000 to $21000 per week
BOATBOOKINGS SAYS:
"Wave your body smoothly like the water while partying in the middle of the Caribbean Leewards on WIND DANCER!"
- Lagoon 55 Crewed Catamaran
- Length: 16.76 m
- Year: 2023
- Cabins: 5
- Berths: 10
- From €35200 to €38500 per week
BOATBOOKINGS SAYS:
"VALINOR is one of the most modern crewed catamarans with 5 cabins in Greece!"
- Fountaine Pajot Crewed Catamaran
- Length: 17 m
- Year: 2025
- Cabins: 6
- Berths: 10
- From $47300 to $57200 per week
BOATBOOKINGS SAYS:
"Stay awake and party all night as you explore the Caribbean waters on this brand-new SAMANA 59!"
- Moon Yacht Crewed Catamaran
- Length: 18 m
- Year: 2024
- Cabins: 4
- Berths: 8
- From €33000 to €46800 per week
BOATBOOKINGS SAYS:
"Be amazed by the things in store for you in Sardinia on the MOON 60 HULL 7 2024."
- Moon Yacht 60 Crewed Catamaran
- Length: 18.32 m
- Year: 2024
- Cabins: 4
- Berths: 8
- From €33000 to €46800 per week
BOATBOOKINGS SAYS:
"Raise your glass and dance to the music on SAIDEIRA in Sardinia!"
- Moon 6TY Luxury Crewed Catamaran
- Length: 19 m
- Year: 2024
- Cabins: 5
- Berths: 10
- From $50000 to $58000 per week
BOATBOOKINGS SAYS:
"Cruise under the Caribbean starry sky on PERFECT MOON!"
- Lagoon Seventy 8 Power Catamaran
- Length: 23 m
- Year: 2024
- Cabins: 4
- Berths: 8
- From $75500 to $80000 per week
BOATBOOKINGS SAYS:
"Get away from stress and live life in the British Virgin Islands on the Lagoon Seventy 8 SIETE MARES!"
- Numarine 26 XP Luxury Crewed Motor Yacht
- Length: 25 m
- Year: 2023
- Cabins: 4
- Berths: 8
- From $60000 to $65000 per week
BOATBOOKINGS SAYS:
"Dive into the alluring water of the Caribbean Leewards and make remarkable memories with your family on EXIT STRATEGY!"
- Sunseeker 95 Luxury Crewed Motor Yacht
- Length: 28 m
- Year: 2023
- 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!"
- Westport 130 Luxury Crewed Motor Yacht
- Length: 39.63 m
- Year: 2005 (2023 Refit)
- Cabins: 5
- Berths: 10
- From $120000 to $138000 per week
BOATBOOKINGS SAYS:
"Live life to the fullest on your Caribbean cruise aboard YOLO!"
