Luxury Yacht Charter in the Leeward Islands

Yacht Charter in the Leeward Islands
Pool with a view!

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!

More information on the Leeward Islands

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

THALIMA
    Southern Wind Shipyard SW110 - 4 Cabins - Caribbean Leeward - Windward - Cannes - Sardinia - Monaco
  • Southern Wind Shipyard SW110 Luxury Crewed Sailing Yacht
  • Length: 33.7 m
  • Year: 2010
  • Cabins: 4
  • Berths: 8
  • From €58000 to €64000 per week
VIEW 2 REVIEWS  Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Sail
  • Length: 33.7 m (114' 10")
  • Year: 2010
VIEW 2 REVIEWS
From €58000 to €64000
per week

BOATBOOKINGS SAYS:
"A superb sailing yacht with an outstanding crew. Do not avoid this winter in the Caribbean or next summer in Sardinia!"

CALLISTA
    Lagoon 620 - 4 Cabins - Tortola - BVI - Grenadines
  • Lagoon 620 Luxury Crewed Catamaran
  • Length: 18.89 m
  • Year: 2016
  • Cabins: 4
  • Berths: 8
  • From $33550 to $39600 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18.89 m (64' 5")
  • Year: 2016
VIEW 1 REVIEW
From $33550 to $39600
per week

BOATBOOKINGS SAYS:
"If youre looking for a full spec, diving, state-of-the-art Lagoon 620 with an expert crew, look no further."

ALIVE!
    Fountaine Pajot Sanya 57 - 5 Cabins - BVI - Tortola - Jost Van Dyke - Peter Island - Anegada
  • Fountaine Pajot Sanya 57 Luxury Crewed Catamaran
  • Length: 17.98 m
  • Year: 2015
  • Cabins: 5
  • Berths: 10
  • From $34500 to $40500 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Catamaran
  • Length: 17.98 m (61' 10")
  • Year: 2015
VIEW 1 REVIEW
From $34500 to $40500
per week

BOATBOOKINGS SAYS:
"Come to life on board ALIVE in the spectacular British Virgin Islands!"

LE REVE
    Lagoon 620 Owners Version - 3 Cabins - Tortola - St Thomas - Leeward Islands - Virgin Islands
  • Lagoon 620 Owners Version Luxury Crewed Catamaran
  • Length: 18.89 m
  • Year: 2017
  • Cabins: 3
  • Berths: 6
  • From $35700 to $42000 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18.89 m (64' 5")
  • Year: 2017
VIEW 1 REVIEW
From $35700 to $42000
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!"

MARE BLU
    Lagoon 630 - 4 Cabins - Grenadines - Tortola - St Marten - BVI
  • Lagoon 630 Luxury Crewed Power Catamaran
  • Length: 64 m
  • Year: 2018
  • Cabins: 4
  • Berths: 8
  • From $36000 to $39000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 64 m (217' 4")
  • Year: 2018
From $36000 to $39000
per week

BOATBOOKINGS SAYS:
"MARE BLU is a luxurious alternative to a sailing catamaran, offering a superb charter around the Caribbean islands."

BLUE PEPPER
    Fountaine Pajot Ipanema 58 - 5 Cabins - Leeward Islands - Virgin Islands - BVI
  • Fountaine Pajot Ipanema 58 Crewed Catamaran
  • Length: 18.28 m
  • Year: 2018
  • Cabins: 5
  • Berths: 10
  • From $35640 to $41480 per week
VIEW 2 REVIEWS  Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18.28 m (62' 4")
  • Year: 2018
VIEW 2 REVIEWS
From $35640 to $41480
per week

BOATBOOKINGS SAYS:
"Outstanding is the word for this crewed catamaran - just have a look at the reviews from clients!"

ZINGARA
    Matrix Silhouette 76 - 5 Cabins - Tortola - Peter Island - Virgin Gorda - Jost Van Dyke - Anegada
  • Matrix Silhouette 76 Luxury Crewed Catamaran
  • Length: 22.34 m
  • Year: 2006 (2017 Refit)
  • Cabins: 5
  • Berths: 10
  • From $42800 to $49100 per week
VIEW 2 REVIEWS  Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Catamaran
  • Length: 22.34 m (75' 2")
  • Year: 2006 (2017 Refit)
VIEW 2 REVIEWS
From $42800 to $49100
per week

BOATBOOKINGS SAYS:
"Zingara never ceases to please those looking for quality sailing and deluxe comfort!"

CHERISH II
    Christensen 120 - 4 Cabins - Nassau - Paradise Island - Virgin Islands - Tortola
  • Christensen 120 Luxury Crewed Motor Yacht
  • Length: 36.58 m
  • Year: 1995 (2013 Refit)
  • Cabins: 4
  • Berths: 8
  • From $65000 to $65000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Motor
  • Length: 36.58 m (124' 10")
  • Year: 1995 (2013 Refit)
From $65000 to $65000
per week

BOATBOOKINGS SAYS:
"Brilliant destination, array of water toys and a crew with a great reputation. CHERISH is fabulous and the only yacht I want to be on for my summer charter adventure!"

ABOVE
    Sunreef 80 - 4 Cabins - Amalfi Coast - Olbia - Sardinia - BVI
  • Sunreef 80 Luxury Crewed Catamaran
  • Length: 24.4 m
  • Year: 2020
  • Cabins: 4
  • Berths: 8
  • From $70000 to $85000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 24.4 m (82' 4")
  • Year: 2020
From $70000 to $85000
per week

BOATBOOKINGS SAYS:
"Brand new SUNREEF 80, available for charters round the stunning Italian Coastlines."

GREAT ADVENTURE
    Lagoon 450 - 3 Cabins - Caribbean - US Virgin Islands - Windward Islands - Leewards Islands - BVI
  • Lagoon 450 Luxury Crewed Catamaran
  • Length: 13.7 m
  • Year: 2014
  • Cabins: 3
  • Berths: 6
  • From $15000 to $18500 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 13.7 m (46' 2")
  • Year: 2014
From $15000 to $18500
per week

BOATBOOKINGS SAYS:
"GREAT ADVENTURE is an immaculate catamaran that is perfect for people who love water sports and scuba diving!"

EXODUS
    Fountaine Pajot Ipanema 58 - BVI - Leeward Islands - Windward Islands
  • Fountaine Pajot Ipanema 58 Luxury Crewed Catamaran
  • Length: 18 m
  • Year: 2015
  • Cabins: 4
  • Berths: 8
  • From $26000 to $30000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18 m (61' )
  • Year: 2015
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!"

LOON
    Newcastle 180 - 6 Cabins - Caribbean - Bahamas - Naples - Sicily - Croatia
  • Newcastle 180 Luxury Crewed Motor Yacht
  • Length: 36.6 m
  • Year: 2011 (Refit 2017)
  • Cabins: 6
  • Berths: 12
  • From $280000 to $300000 per week
Details Enquire
  • Berths: 12
  • Cabins: 6
  • Crew: Crewed
  • Type: Motor
  • Length: 36.6 m (124' )
  • Year: 2011 (Refit 2017)
From $280000 to $300000
per week

BOATBOOKINGS SAYS:
"The ultimate luxury escape, with fabulous entertainment areas and a stunning infinity pool."

SAIL AWAY
    Lagoon 620 - 5 Cabins - BVI - Tortola - Beef Island - Virgin Gorda
  • Lagoon 620 Luxury Crewed Catamaran
  • Length: 18.9 m
  • Year: 2014
  • Cabins: 5
  • Berths: 10
  • From $30000 to $38000 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18.9 m (64' 5")
  • Year: 2014
VIEW 1 REVIEW
From $30000 to $38000
per week

BOATBOOKINGS SAYS:
"She has sophisticated touches throughout with a dedicated crew, perfect for your next family yacht charter."

CROCODILE DADDY
    Lagoon 620 - 4 Cabins - Western Mediteranean - Caribbean - Virgin Islands
  • Lagoon 620 Crewed Catamaran
  • Length: 18.9 m
  • Year: 2010
  • Cabins: 4
  • Berths: 8
  • From €23000 to €25000 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18.9 m (64' 5")
  • Year: 2010
VIEW 1 REVIEW
From €23000 to €25000
per week

BOATBOOKINGS SAYS:
"One of the best crewed Catamarans on the French Riviera!"

MUSE
    Sunreef 70 - 6 Cabins - BVI - St Martin - St Barths - Tortola - Palma - Monaco - Naples
  • Sunreef 70 Luxury Crewed Catamaran
  • Length: 21.34 m
  • Year: 2011
  • Cabins: 6
  • Berths: 12
  • From €32000 per week
Details Enquire
  • Berths: 12
  • Cabins: 6
  • Crew: Crewed
  • Type: Catamaran
  • Length: 21.34 m (72' 10")
  • Year: 2011
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."

PIPE DREAM
    Westport 130 - 5 Staterooms - Bahamas - Nassau - Paradise Island - Georgetown - St Thomas - St Barths
  • Westport 130 Luxury Crewed Motor Yacht
  • Length: 39.62 m
  • Year: 2014
  • Cabins: 5
  • Berths: 10
  • From $125000 to $140000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 39.62 m (134' 1")
  • Year: 2014
From $125000 to $140000
per week

BOATBOOKINGS SAYS:
"The leading 130 Westport cruising the Bahamas and Caribbean,offering unrivalled amenities, accommodation and entertainment areas. She provides the whole package!"

SCORPION
    San Lorenzo 46m - 5 Cabins - Monaco - Cannes - St Tropez - Naples - Capri
  • San Lorenzo 46m Luxury Crewed Motor Yacht
  • Length: 46 m
  • Year: 2015
  • Cabins: 5
  • Berths: 12
  • From €245000 per week
Details Enquire
  • Berths: 12
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 46 m (156' 4")
  • Year: 2015
From €245000
per week

BOATBOOKINGS SAYS:
"This exceptional superyacht radiates magnificence, stunning inside and out."

BAGHEERA
    Lagoon 620 - 4 Cabins - Tortola - Virgin Gorda - BVI
  • Lagoon 620 Luxury Crewed Catamaran
  • Length: 18.89 m
  • Year: 2018
  • Cabins: 4
  • Berths: 8
  • From $35000 to $39800 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18.89 m (64' 5")
  • Year: 2018
From $35000 to $39800
per week

BOATBOOKINGS SAYS:
"A standout charter yacht with a vastly experienced crew; Alex, Carla and Beatrix will not disappoint!"

Lagoon 57
    Day Charter and Week Long Charter - 2017 - 4 Cabins (4 cabins) - Tortola - BVI
  • Day Charter and Week Long Charter Luxury Crewed Catamaran
  • Length: 57 m
  • Year: 1995
  • Cabins: 4
  • Berths: 4
  • From $3500 to $12990 per day
Details Enquire
  • Berths: 4
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 57 m (193' )
  • Year: 1995
From $3500 to $12990
per day

BOATBOOKINGS SAYS:
"Fantastic day charter, with the option of chartering for a week in the unrivalled BVI!"

CALMAO
    Sunreef 74 - 4 Cabins - BVI - Tortola - Palma - Ibiza - Formentera
  • Sunreef 74 Luxury Crewed Catamaran
  • Length: 22.56 m
  • Year: 2017
  • Cabins: 4
  • Berths: 9
  • From €39000 to €43000 per week
VIEW 3 REVIEWS  Details Enquire
  • Berths: 9
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 22.56 m (76' )
  • Year: 2017
VIEW 3 REVIEWS
From €39000 to €43000
per week

BOATBOOKINGS SAYS:
"Striking, suave and beautifully eye-catching, CALMAO is ready and raring to explore the Caribbean and Mediterranean. Book now or you will miss out!"

ARAOK
    Fountaine Pajot Ipanema 58 - 3 Cabins - Cannes - Monaco - St Tropez - Bonifacio - Porto Cervo - Tortola:
  • Fountaine Pajot Ipanema 58 Luxury Crewed Catamaran
  • Length: 17.8 m
  • Year: 2018
  • Cabins: 3
  • Berths: 6
  • From €24000 to €28000 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 17.8 m (60' 4")
  • Year: 2018
VIEW 1 REVIEW
From €24000 to €28000
per week

ANANDA
    Swan 82 - 3 Cabins - Virgin Gorda - Tortola - St. Marteen - Grenada - Cannes - Monaco
  • Swan 82 Luxury Crewed Sailing Yacht
  • Length: 24.9 m
  • Year: 2012
  • Cabins: 3
  • Berths: 6
  • From $39500 to $42500 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Sail
  • Length: 24.9 m (84' 6")
  • Year: 2012
From $39500 to $42500
per week

BOATBOOKINGS SAYS:
"Built for high performance sailing, whilst offering elegance and opulence both above and below deck!"

MAYRILOU
    Sunreef Supreme 68 - 5 Cabins - Cannes - Naples - Sicily - Dubrovnik
  • Sunreef Supreme 68 Luxury Crewed Catamaran
  • Length: 20.73 m
  • Year: 2017
  • Cabins: 5
  • Berths: 10
  • From €38000 to €45000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Catamaran
  • Length: 20.73 m (70' 9")
  • Year: 2017
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."

BELLA RAGAZZA
    Vitters 43m - 5 Cabins - Caribbean - Leeward islands - Virgin Island - Spain/Balearics - Corsica - Sardinia
  • Vitters 43m Luxury Crewed Sailing Yacht
  • Length: 43 m
  • Year: 2004 (2012 Refit)
  • Cabins: 5
  • Berths: 10
  • From €98000 to €112000 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Sail
  • Length: 43 m (146' 4")
  • Year: 2004 (2012 Refit)
VIEW 1 REVIEW
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."

BLUE GRYPHON
    Prout 83 - 5 Cabins - Leeward Islands - Windward Islands - Virgin Islands
  • Prout 83 Luxury Crewed Catamaran
  • Length: 25.3 m
  • Year: 2013 (2017 Refit)
  • Cabins: 5
  • Berths: 12
  • From $60000 to $74000 per week
Details Enquire
  • Berths: 12
  • Cabins: 5
  • Crew: Crewed
  • Type: Catamaran
  • Length: 25.3 m (86' 10")
  • Year: 2013 (2017 Refit)
From $60000 to $74000
per week

BOATBOOKINGS SAYS:
"Impressive sailing catamaran with vast exterior space!"

BLU 470
    Feadship 50m - 5 Cabins - Monaco - Cannes - Bahamas - Caribbean
  • Feadship 50m Luxury Crewed Motor Yacht
  • Length: 49.68 m
  • Year: 1990 (2014 Refit)
  • Cabins: 5
  • Berths: 10
  • From $185000 to $210000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 49.68 m (168' )
  • Year: 1990 (2014 Refit)
From $185000 to $210000
per week

BOATBOOKINGS SAYS:
"BLU 470 is a fantastic crewed motor yacht for charter in the Mediterranean or Caribbean!"

TRANQUILITY
    Matrix Silhouette 76 - 6 Cabins - BVI - Tortola - Virgin Gorda - Jost Van Dyke
  • Matrix Silhouette 76 Luxury Crewed Catamaran
  • Length: 23.16 m
  • Year: 2013
  • Cabins: 6
  • Berths: 12
  • From $56950 to $59950 per week
VIEW 3 REVIEWS  Details Enquire
  • Berths: 12
  • Cabins: 6
  • Crew: Crewed
  • Type: Catamaran
  • Length: 23.16 m (78' )
  • Year: 2013
VIEW 3 REVIEWS
From $56950 to $59950
per week

BOATBOOKINGS SAYS:
"This is a unique, huge and extremely luxurious Catamaran - a Boatbookings favourite!"

SUR LEAU
    Privilege 74 - 4 Cabins - Virgin Islands - Leeward Islands
  • Privilege 74 Luxury Crewed Catamaran
  • Length: 22.68 m
  • Year: 2011
  • Cabins: 4
  • Berths: 8
  • From $48000 to $54000 per week
VIEW 2 REVIEWS  Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 22.68 m (77' )
  • Year: 2011
VIEW 2 REVIEWS
From $48000 to $54000
per week

BOATBOOKINGS SAYS:
"Queen of the Cats in the BVI - we highly recommend the boat and their crew."

REEL TIGHT
    Merritt 86 - 5 cabins - Boca Raton - Nassau - Virgin Islands - Windwards/Leewards - Mexico
  • Merritt 86 Fishing Boat
  • Length: 26.21 m
  • Year: 2017
  • Cabins: 5
  • Berths: 10
  • From $70000 to $70000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 26.21 m (89' 5")
  • Year: 2017
From $70000 to $70000
per week

BOATBOOKINGS SAYS:
"Fishing has never been so luxurious than onboard REEL TIGHT."

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