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

Displaying: Your Search Results in Leeward Islands
LE REVE - Lagoon 620 Owners Version - 3 Cabins - Tortola - St Thomas - Leeward Islands - Virgin Islands VIEW 1 REVIEW 
LE REVE
    Lagoon 620 Owners Version - 3 Cabins - Tortola - St Thomas - Leeward Islands - Virgin Islands
  • Lagoon 620 Owners Version Crewed Catamaran
  • Length: 18.89 m
  • Year: 2017
  • Cabins: 3
  • Berths: 6
  • From $34000 to $38000 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 $34000 to $38000
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!"

CALLISTA - Lagoon 620 - 4 Cabins - Tortola - BVI - Grenadines
CALLISTA
    Lagoon 620 - 4 Cabins - Tortola - BVI - Grenadines
  • Lagoon 620 Crewed Sailing Catamaran
  • Length: 18.89 m
  • Year: 2016
  • Cabins: 4
  • Berths: 8
  • From $30000 to $35000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18.89 m (64' 5")
  • Year: 2016
From $30000 to $35000
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."

ORION - Sunreef 74 - 4 Cabins - Caribbean - BVI -  Aeolian Islands - Milazzo VIEW 1 REVIEW 
ORION
    Sunreef 74 - 4 Cabins - Caribbean - BVI - Aeolian Islands - Milazzo
  • Sunreef 74 Crewed Catamaran
  • Length: 22.5 m
  • Year: 2017
  • Cabins: 4
  • Berths: 8
  • From $45000 to $51000 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 22.5 m (76' 6")
  • Year: 2017
VIEW 1 REVIEW
From $45000 to $51000
per week

BOATBOOKINGS SAYS:
"One of our most recommended crews found on one of the most luxurious catamarans, not to be missed in the Caribbean / Italy this season."

ALIVE! - Fountaine Pajot Sanya 57 - 5 Cabins - BVI - Tortola - Jost Van Dyke - Peter Island - Anegada VIEW 1 REVIEW 
ALIVE!
    Fountaine Pajot Sanya 57 - 5 Cabins - BVI - Tortola - Jost Van Dyke - Peter Island - Anegada
  • Fountaine Pajot Sanya 57 Crewed Catamaran
  • Length: 17.98 m
  • Year: 2015
  • Cabins: 5
  • Berths: 10
  • From $28290 to $31900 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 $28290 to $31900
per week

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

DIANA - Sunreef 74 - 4 Cabins - Antigua - Caribbean Leeward - Virgin Islands - Carribean Windward
DIANA
    Sunreef 74 - 4 Cabins - Antigua - Caribbean Leeward - Virgin Islands - Carribean Windward
  • Sunreef 74 Luxury Crewed Catamaran
  • Length: 22.56 m
  • Year: 2017
  • Cabins: 4
  • Berths: 8
  • From $49000 to $52500 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 22.56 m (76' )
  • Year: 2017
From $49000 to $52500
per week

BOATBOOKINGS SAYS:
"A well designed luxury catamaran perfect for any occasion."

LUCY Z - Sunreef 74 - 3 Cabins - St Barts - Leeward Islands - Windward Islands - Caribbean Sea
LUCY Z
    Sunreef 74 - 3 Cabins - St Barts - Leeward Islands - Windward Islands - Caribbean Sea
  • Sunreef 74 Crewed Catamaran
  • Length: 22.55 m
  • Year: 2015
  • Cabins: 5
  • Berths: 7
  • From $47000 to $51000 per week
Details Enquire
  • Berths: 7
  • Cabins: 5
  • Crew: Crewed
  • Type: Catamaran
  • Length: 22.55 m (76' 11")
  • Year: 2015
From $47000 to $51000
per week

BOATBOOKINGS SAYS:
"A meticulously custom-designed crewed charter yacht for luxurious sailing adventures throughout the Caribbean"

NEVER ENOUGH - Trinity 157 - 5 Cabins - Bahamas - Nassau - Caribbean - Miami - Florida
NEVER ENOUGH
    Trinity 157 - 5 Cabins - Bahamas - Nassau - Caribbean - Miami - Florida
  • Trinity 157 Luxury Crewed Motor Yacht
  • Length: 47.85 m
  • Year: 2006 (2014 Refit)
  • Cabins: 5
  • Berths: 11
  • From $150000 per week
Details Enquire
  • Berths: 11
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 47.85 m (162' 9")
  • Year: 2006 (2014 Refit)
From $150000
per week

BOATBOOKINGS SAYS:
"This glorious luxury yacht is the perfect charter yacht for guests wanting unadulterated luxury to sail the Caribbean and Bahamas!"

DONA LOLA - Westport 130 - 5 Staterooms - St Martin - St Barths - Anguilla
DONA LOLA
    Westport 130 - 5 Staterooms - St Martin - St Barths - Anguilla
  • Westport 130 Luxury Motor Yacht
  • Length: 39.6 m
  • Year: 2003 (2010 Refit)
  • Cabins: 5
  • Berths: 10
  • From $90000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Motor
  • Length: 39.6 m (134' )
  • Year: 2003 (2010 Refit)
From $90000
per week

BOATBOOKINGS SAYS:
"A special elegant yacht with a 5 star crew"

BLUE PEPPER - Fountaine Pajot Ipanema 58 - 5 Cabins - Leeward Islands - Virgin Islands - BVI
BLUE PEPPER
    Fountaine Pajot Ipanema 58 - 5 Cabins - Leeward Islands - Virgin Islands - BVI
  • Fountaine Pajot Ipanema 58 Crewed Sailing Catamaran
  • Length: 18.28 m
  • Year: 2018
  • Cabins: 5
  • Berths: 10
  • From $27200 to $31400 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Catamaran
  • Length: 18.28 m (62' 4")
  • Year: 2018
From $27200 to $31400
per week

ZINGARA - Matrix Silhouette 76 - 5 Cabins - Tortola - Peter Island - Virgin Gorda - Jost Van Dyke - Anegada VIEW 1 REVIEW 
ZINGARA
    Matrix Silhouette 76 - 5 Cabins - Tortola - Peter Island - Virgin Gorda - Jost Van Dyke - Anegada
  • Matrix Silhouette 76 Crewed Sailing Catamaran
  • Length: 22.34 m
  • Year: 2006 (2017 Refit)
  • Cabins: 5
  • Berths: 10
  • From $42800 to $49100 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Catamaran
  • Length: 22.34 m (75' 2")
  • Year: 2006 (2017 Refit)
VIEW 1 REVIEW
From $42800 to $49100
per week

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

EXODUS - Fountaine Pajot 59 - BVI - Leeward Islands - Windward Islands
EXODUS
    Fountaine Pajot 59 - BVI - Leeward Islands - Windward Islands
  • Fountaine Pajot 59 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!"

AFRICA I - Benetti 154 - 6 Cabins - St Marteen - Windward Islands - Antigua - Panama - Split - Dubrovnik - Monaco - Cannes
AFRICA I
    Benetti 154 - 6 Cabins - St Marteen - Windward Islands - Antigua - Panama - Split - Dubrovnik - Monaco - Cannes
  • Benetti 154 Luxury Crewed Motor Yacht
  • Length: 47 m
  • Year: 2010 (2018 Refit)
  • Cabins: 6
  • Berths: 12
  • From €196000 to €217000 per week
Details Enquire
  • Berths: 12
  • Cabins: 6
  • Crew: Crewed
  • Type: Motor
  • Length: 47 m (159' 8")
  • Year: 2010 (2018 Refit)
From €196000 to €217000
per week

BOATBOOKINGS SAYS:
"Stunning Benetti Yacht recently refitted and in pristine condition ready for your charter!"

SOVEREIGN - Newcastle 180 - 6 Cabins - Caribbean - Bahamas - Naples - Sicily - Croatia
SOVEREIGN
    Newcastle 180 - 6 Cabins - Caribbean - Bahamas - Naples - Sicily - Croatia
  • Newcastle 180 Luxury Motor Yacht
  • Length: 36.6 m
  • Year: 2011 (Refit 2017)
  • Cabins: 6
  • Berths: 12
  • From €275000 to €295000 per week
Details Enquire
  • Berths: 12
  • Cabins: 6
  • Crew: Crewed
  • Type: Motor
  • Length: 36.6 m (124' )
  • Year: 2011 (Refit 2017)
From €275000 to €295000
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 VIEW 1 REVIEW 
SAIL AWAY
    Lagoon 620 - 5 Cabins - BVI - Tortola - Beef Island - Virgin Gorda
  • Lagoon 620 Crewed Catamaran
  • Length: 18.9 m
  • Year: 2014
  • Cabins: 5
  • Berths: 10
  • From $29000 to $36000 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 $29000 to $36000
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 VIEW 1 REVIEW 
CROCODILE DADDY
    Lagoon 620 - 4 Cabins - Western Mediteranean - Caribbean - Virgin Islands
  • Lagoon 620 Crewed Sailing Catamaran
  • Length: 18.9 m
  • Year: 2010
  • Cabins: 4
  • Berths: 8
  • From €23000 to €26000 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 €26000
per week

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

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