Caribbean Charter Yachts
Perhaps no other destination in the world can offer such a dynamic atmosphere and environment. The Caribbean is made up of two different island groups, the Leeward and the Windward Islands, both groups provide near- consistent winds and provide ideal sailing conditions for the sailing enthusiasts out there!
Boatbookings has hundreds of charter yachts in the Caribbean: Motor, Sail, Catamarans, Super and Mega Yachts, as well as Bareboat Charters. In all the hot spots such as the BVI (British Virgin Islands), Grenadines, St Barts & St Martin - wherever you want to charter a yacht! We invite you to browse through our yachts below, and then contact on of our experts and we'll find that perfect yacht for your next yacht charter vacation!
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
- Nautor Swan 100 S Luxury Crewed Sailing Yacht
- Length: 30.21 m
- Year: 2005 (2021 Refit)
- Cabins: 3
- Berths: 6
- From €55000 to €62000 per week
BOATBOOKINGS SAYS:
"Dark in name, sharp in tone, the Balearics and the Caribbean Leewards move differently aboard ONYX!"
- Jeanneau 64 Luxury Crewed Sailing Yacht
- Length: 19 m
- Year: 2018 (2025 Refit)
- Cabins: 3
- Berths: 6
- From $23000 to $25000 per week
BOATBOOKINGS SAYS:
"Get your summer bod ready for your next exhilarating Caribbean exploration on BODHISATTVA!"
- Oyster 655 Luxury Crewed Sailing Yacht
- Length: 19.81 m
- Year: 2008 (2025 Refit)
- Cabins: 2
- Berths: 4
- From $24000 to $26400 per week
BOATBOOKINGS SAYS:
"Where island days and cool winds swirl, coast to coast belongs to JERSEY GIRL!"
- Advance Yacht A80 Bareboat Sailing Yacht
- Length: 23 m
- Year: 2021
- Cabins: 3
- Berths: 6
- From €34000 per week
BOATBOOKINGS SAYS:
"Leave Sardinia filled with blissful memories aboard MINDFULNESS."
- Solaris 24m Luxury Crewed Sailing Yacht
- Length: 24 m
- Year: 2024
- Cabins: 3
- Berths: 6
- From €30000 to €35000 per week
BOATBOOKINGS SAYS:
"Chase winter in the Caribbean and summer in the Western Mediterranean aboard AMURI, the 24-meter Solaris yacht that makes every season worth following!"
- YYacht Y9 Luxury Crewed Sailing Yacht
- Length: 29.71 m
- Year: 2025
- Cabins: 4
- Berths: 9
- From €53000 to €60000 per week
BOATBOOKINGS SAYS:
"EPHEMERE glides with coastal flair through Croatia’s bays so fair, turning passing hours into treasures you will always want to share."
- Fitzroy 38m Luxury Crewed Sailing Yacht
- Length: 38.9 m
- Year: 2006 (2022 Refit)
- Cabins: 4
- Berths: 10
- From €98000 to €112000 per week
BOATBOOKINGS SAYS:
"Big summer surprises await to be unwrapped as you visit Greece's astounding anchorages in your luxurious sailing vacation on DAKOTA!"
- Jongert 138 Crewed Sailing Yacht
- Length: 42 m
- Year: 2002 (2024 Refit)
- Cabins: 3
- Berths: 6
- From $90000 per week
BOATBOOKINGS SAYS:
"Glide on enchanting waters and have an exhilarating exploration of the Caribbean waters on ABIDE!"
- Ark Yachts 54m Luxury Crewed Sailing Yacht
- Length: 54 m
- Year: 2013 (2023 Refit)
- Cabins: 13
- Berths: 26
- From €85000 to €95000 per week
BOATBOOKINGS SAYS:
"Time is of the essence so spend it with loved ones discovering the vibrant French Riviera on CHRONOS!"
- Perini Navi 56m Luxury Crewed Sailing Yacht
- Length: 56 m
- Year: 2004 (2025 Refit)
- Cabins: 6
- Berths: 12
- From €230000 to €245000 per week
BOATBOOKINGS SAYS:
"Between cliffside villages and open horizons, ZENJI brings a composed way to experience the Amalfi Coast!"
- 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."
- 38m Schooner Gulet
- Length: 38 m
- Year: 2007 (2014 Refit)
- Cabins: 9
- Berths: 18
- From €35000 per week
BOATBOOKINGS SAYS:
"A great looking boat, a head turner, perfect for entertaining."
- Royal Huisman 47m Luxury Crewed Sailing Yacht
- Length: 47.42 m
- Year: 1998 (2015 Refit)
- Cabins: 3
- Berths: 6
- From $112000 to $135000 per week
BOATBOOKINGS SAYS:
"A sensational sailing yacht for family adventures around the Caribbean."
- Hylass 70 Crewed Sailing Yacht
- Length: 21.34 m
- Year: 2009
- Cabins: 3
- Berths: 6
- From $17000 to $19000 per week
BOATBOOKINGS SAYS:
"Experience a royal treatment aboard THE ROYAL BLUE in your Caribbean sailing yacht charter."
- Palmer Johnson 123 luxury Crewed Sailing Yacht
- Length: 37.49 m
- Year: 1990 (2007 Refit)
- Cabins: 3
- Berths: 6
- From €46000 to €55000 per week
BOATBOOKINGS SAYS:
"A superlative sailing yacht that will make dreams come true."
- Perini Navi 164 Luxury Crewed Sailing Yacht
- Length: 49.8 m
- Year: 2000
- Cabins: 5
- Berths: 12
- From $175000 to $190000 per week
BOATBOOKINGS SAYS:
"ALMYRA II offers a perfect blend of comfort and class served by a top-notch crew!"
- Perini Navi 52m Luxury Crewed Sailing Yacht
- Length: 52 m
- Year: 1997 (2007 Refit)
- Cabins: 5
- Berths: 10
- From €175000 to €189000 per week
BOATBOOKINGS SAYS:
"Her spacious flybridge is almost full-beam in width and is ideal for alfresco dining!"
- 5 cabins Bareboat Sailing Yacht
- Length: 15.2 m
- Year: 2020
- Cabins: 5
- Berths: 10
- From $5210 to $12065 per week
- 2018 Bareboat Sailboat
- Length: 15.75 m
- Year: 2018
- Cabins: 6
- Berths: 11
- From $5210 to $12605 per week
BOATBOOKINGS SAYS:
"Stunning Sun Odyssey 519 perfect for a large group of friends or family to explore the dazzling islands of the USVI!"
- 5 Cabins (5 Doubles + 1 Single) Bareboat Sailing Yacht
- Length: 15.94 m
- Year: 2020
- Cabins: 6
- Berths: 11
- From $5210 to $10745 per week
BOATBOOKINGS SAYS:
"Luxurious monohull yacht suitable for large groups or families!"
- 3 Cabins Bareboat Sailing Yacht
- Length: 14.15 m
- Year: 2017
- Cabins: 3
- Berths: 8
- From $2450 to $8000 per week
BOATBOOKINGS SAYS:
"2017 brings you this Dufour 460 Grand Large sailing Tortola and the BVI"
- Sailing Yacht 68ft Crewed Sailing Yacht
- Length: 20 m
- Year: 2024
- Cabins: 3
- Berths: 6
- From $29500 to $34000 per week
BOATBOOKINGS SAYS:
"Let the wind take you to magical Leeward Island vistas on CIRRUS!"
- Swan 78 Sailing Yacht
- Length: 23 m
- Year: 2024
- Cabins: 3
- Berths: 6
- From $48000 to $52000 per week
BOATBOOKINGS SAYS:
"Leewards is a true bliss, a vacation well-spent onboard OPTIMIST!"
- Oyster 885 Luxury Crewed Sailing Yacht
- Length: 27 m
- Year: 2025
- Cabins: 4
- Berths: 8
- From $65000 per week
BOATBOOKINGS SAYS:
"Under skies so blue and waters aglow, Antigua comes alive when you’re on SUNYO!"
- Alloy 104 Luxury Crewed Sailing Yacht
- Length: 31 m
- Year: 1996 (2025 Refit)
- Cabins: 3
- Berths: 6
- From €42000 to €48000 per week
BOATBOOKINGS SAYS:
"Experience the vibrance of French Polynesia on ABUNDANCE, with a proactive crew taking you to the wonders of Tahiti!"
- Custom Build Gulet
- Length: 35.5 m
- Year: 2009
- Cabins: 6
- Berths: 12
- From €61250 to €61250 per week
BOATBOOKINGS SAYS:
"Probably the most luxurious motor sailer currently in the Greek market. Cherry wood interiors, marble bathrooms, the owner has paid attention to every single detail. Wonderful crew, suberb dining! A must!"
- 116 Holland Jachtbouw Luxury Crewed Sailing Yacht
- Length: 35 m
- Year: 2003
- Cabins: 3
- Berths: 6
- From $75000 to $86250 per week
BOATBOOKINGS SAYS:
"Perfect for entertaining family and friends."
- Bareboat Sailing Yacht
- Length: 12 m
- Year: 2018
- Cabins: 3
- Berths: 6
- From $3400 to $4750 per week
BOATBOOKINGS SAYS:
"The ideal sailing boat to explore the BVI, with sailing prowess and all the modern amenities."
- 4 + 2 Cabins (4 Double 2 Single) Bareboat Sailing Yacht
- Length: 13.72 m
- Year: 2017
- Cabins: 6
- Berths: 10
- From $4818 to $10794 per week
BOATBOOKINGS SAYS:
"A stunning Bali 4.5 ready for charters in the Baja Peninsula!"
- 5 Cabins Bareboat Sailing Yacht
- Length: 14.6 m
- Year: 2013
- Cabins: 5
- Berths: 12
- From $2950 to $6900 per week
BOATBOOKINGS SAYS:
"Modern, comfortable and stylish. This Oceanis 48 is beautifully equipped with all the necessities for a successful sailing holiday in the Caribbean!"
