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Caribbean Charter Yachts
  The Caribbean is without doubt one of the most perfect destinations to charter a yacht with your family and friends - it is the ultimate tropical paradise for a sailing holiday with stunning ...

Windward Islands Charter Yachts and Sailing Vacations 2026-2027
A Stunning Beach in the Windward Islands Explore the wonderful Windward Islands in 2026 and 2027 from the unrivaled comfort of a luxury motor yacht charter or crewed catamaran and discover an... There are 1 additional articles in this category.

The Best St Lucia Crewed Yacht Charter for 2026 and 2027 | Windward Islands
Sailing St Lucia A Crewed Luxury Yacht Charter is the Perfect way to Explore St. Lucia during 2026 and 2027 Situated in the heart of the Windward Islands, St Lucia's variety makes it unique ...

Discover our selection of yachts below and contact our Charter Experts at Boatbookings to receive a bespoke proposal and embark on the ultimate yacht charter vacation.

Let us take over and do the work for you by completing our enquiry form. Or, contact us directly at [email protected] with details of your group size, type of yacht, destination and budget. One of our Charter Experts will call you so please leave your phone number.

We look forward to hearing from you!

ILLUSION - Nautitech 46 - 3 Cabins - Martinique - Grenadines - Union Island - St Lucia
ILLUSION
    Nautitech 46 - 3 Cabins - Martinique - Grenadines - Union Island - St Lucia
  • Nautitech 46 Luxury Crewed Catamaran
  • Length: 14.02 m
  • Year: 2019
  • Cabins: 3
  • Berths: 6
  • From $15000 to $18000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 14.02 m (47' 10")
  • Year: 2019
From $15000 to $18000
per week

BOATBOOKINGS SAYS:
"You will be dazzled by the beauty of the Nautitech 46 ILLUSION and the knowledge of Captain Bruno. Our previous charter feedback is always exceptional, so there is no better catamaran to cruise the Grenadines."

MY MARINA - Bali 4.8 - 3 Cabins - St Vincent - St Lucia - Grenada - Windwards - Caribbean
MY MARINA
    Bali 4.8 - 3 Cabins - St Vincent - St Lucia - Grenada - Windwards - Caribbean
  • Bali 4.8 Luxury Crewed Catamaran
  • Length: 14 m
  • Year: 2022
  • Cabins: 3
  • Berths: 6
  • From $15000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 14 m (47' 8")
  • Year: 2022
From $15000
per week

BOATBOOKINGS SAYS:
"For sunshine that is sweeter and blue water that is cleaner, chart your escape aboard MY MARINA through the Caribbean Windwards."

LYRA - Fountaine Pajot Alegria 67 - 5 Cabins - St Vincent - St Lucia - Grenada - Windwards - Caribbean
LYRA
    Fountaine Pajot Alegria 67 - 5 Cabins - St Vincent - St Lucia - Grenada - Windwards - Caribbean
  • Fountaine Pajot Alegria 67 Luxury Crewed Catamaran
  • Length: 20 m
  • Year: 2021 (2025 Refit)
  • Cabins: 5
  • Berths: 10
  • From $55000 to $63000 per week
Details Enquire
  • Berths: 10
  • Cabins: 5
  • Crew: Crewed
  • Type: Catamaran
  • Length: 20 m (68' 8")
  • Year: 2021 (2025 Refit)
From $55000 to $63000
per week

BOATBOOKINGS SAYS:
"The Caribbean waves are just music to the ears while aboard LYRA!"

SEACLUSION - Sunreef 80 - 4 Cabins - Grenada - St Vincent - Windwards - Caribbean VIEW 1 REVIEW 
SEACLUSION
    Sunreef 80 - 4 Cabins - Grenada - St Vincent - Windwards - Caribbean
  • Sunreef 80 Luxury Crewed Catamaran
  • Length: 23.99 m
  • Year: 2020 (2023 Refit)
  • Cabins: 4
  • Berths: 8
  • From $60000 to $80000 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 23.99 m (81' 11")
  • Year: 2020 (2023 Refit)
VIEW 1 REVIEW
From $60000 to $80000
per week

BOATBOOKINGS SAYS:
"SEACLUSION is one of the top catamarans chartering the Caribbean and has won the Best Yacht in the 2022 USVI Yacht Show!"

SEA DANCER - Leopard 45 - 3 Cabins - Grenada - Trinidad - Tobago - Barbados - Windwards - Caribbean
SEA DANCER
    Leopard 45 - 3 Cabins - Grenada - Trinidad - Tobago - Barbados - Windwards - Caribbean
  • Leopard 45 Crewed Catamaran
  • Length: 13 m
  • Year: 2020
  • Cabins: 3
  • Berths: 6
  • From $19500 to $21500 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Catamaran
  • Length: 13 m (44' 4")
  • Year: 2020
From $19500 to $21500
per week

BOATBOOKINGS SAYS:
"Get ready to shake to the Caribbean groove on SEA DANCER!"

GROOVY - Robertson and Caine 42 - 4 Cabins - Grenadines - Grenada - Leeward Islands - Windward Islands VIEW 1 REVIEW 
GROOVY
    Robertson and Caine 42 - 4 Cabins - Grenadines - Grenada - Leeward Islands - Windward Islands
  • Robertson and Caine 42 Crewed Catamaran
  • Length: 13 m
  • Year: 2011
  • Cabins: 4
  • Berths: 7
  • From $13950 to $17150 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 7
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 13 m (44' 4")
  • Year: 2011
VIEW 1 REVIEW
From $13950 to $17150
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 from the Windwards to Leewards!"

CHAMPAGNE HIPPY - Oyster 825 - 4 Cabins - Palma de Mallorca - Menorca - Ibiza
CHAMPAGNE HIPPY
    Oyster 825 - 4 Cabins - Palma de Mallorca - Menorca - Ibiza
  • Oyster 825 Crewed Sailing Yacht
  • Length: 25 m
  • Year: 2014
  • Cabins: 0
  • Berths: 8
  • From €30000 to €34000 per week
Details Enquire
  • Berths: 8
  • Cabins: 0
  • Crew: Crewed
  • Type: Sail
  • Length: 25 m (85' 4")
  • Year: 2014
From €30000 to €34000
per week

BOATBOOKINGS SAYS:
"A perfect boat for sailing with family!"

ENTRE4 - Sunreef 80 - 4 Cabins - St Vincent - The Grenadines - Windwards - Caribbean VIEW 1 REVIEW 
ENTRE4
    Sunreef 80 - 4 Cabins - St Vincent - The Grenadines - Windwards - Caribbean
  • Sunreef 80 Luxury Crewed Catamaran
  • Length: 23 m
  • Year: 2024
  • Cabins: 4
  • Berths: 8
  • From $94000 to $100000 per week
VIEW 1 REVIEW  Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 23 m (78' 8")
  • Year: 2024
VIEW 1 REVIEW
From $94000 to $100000
per week

BOATBOOKINGS SAYS:
"Enter the hidden paradises of the Caribbean Islands on ENTRE4!"

OPTIMIST - Swan 78 - 3 Cabins - Antigua - Barbuda - Leewards - Windwards - Caribbean
OPTIMIST
    Swan 78 - 3 Cabins - Antigua - Barbuda - Leewards - Windwards - Caribbean
  • Swan 78 Sailing Yacht
  • Length: 23 m
  • Year: 2024
  • Cabins: 3
  • Berths: 6
  • From $48000 to $52000 per week
Details Enquire
  • Berths: 6
  • Cabins: 3
  • Crew: Crewed
  • Type: Sail
  • Length: 23 m (78' 8")
  • Year: 2024
From $48000 to $52000
per week

BOATBOOKINGS SAYS:
"Leewards is a true bliss, a vacation well-spent onboard OPTIMIST!"

LITTLE GIANT - Sunreef 88 Double Deck - 4 Cabins - St. Martin - St. Barths - Anguilla - Leeward Islands - Caribbean
LITTLE GIANT
    Sunreef 88 Double Deck - 4 Cabins - St. Martin - St. Barths - Anguilla - Leeward Islands - Caribbean
  • Sunreef 88 Double Deck Luxury Crewed Catamaran
  • Length: 26 m
  • Year: 2017
  • Cabins: 4
  • Berths: 8
  • From $94000 to $100000 per week
Details Enquire
  • Berths: 8
  • Cabins: 4
  • Crew: Crewed
  • Type: Catamaran
  • Length: 26 m (88' 8")
  • Year: 2017
From $94000 to $100000
per week

BOATBOOKINGS SAYS:
"Experience both luxury and relaxation aboard LITTLE GIANT as you sail through the Caribbean with her bounty of water toys and ample deck space."

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