
Sailboats in the Caribbean & Virgin Islands
Are you a sailboat & monohull traditionalist? Nothing compares to skimming across the calm turquoise colored water under crisp white sails. You needn’t worry if you’ve never sailed before, as your professional crew takes care of all the details of handling the yacht. You can choose to join in with the raising the sails or simply sit & enjoy the wonderful experience! Charter sailing yachts have large cockpits where you can lounge, read, chat with friends, and enjoy meals in the Caribbean breeze. An awning provides protection from the sun, while the foredeck is a great place for sunbathing. Belowdecks you will find an airy main salon and dining area as well as large guest cabins with private bathrooms. Crew cabins will be separate from guest accommodations.
We represent many more crewed charter sailboat monohulls than shown here, so please inquire for one that fits your budget!
Abide
138' | USVI, BVI | 8 Guests-4 Cabins
All-Inclusive & newly refitted in 2024! Luxury meets perfect harmony for those who cherish elegance and the allure of untouched anchorages. With a total crew of 5, Captain & Chef Roland and Vanessa, both vibrant, energetic and charming hosts are avid scuba diver/free divers. See their sample menu!
8 Days/ 7 Nights
From:
$90,000
Aurelius
111' | SXM-St. Barts & Newport | 6 Guests-3 Cabins
Has a master cabin with Queen bed & ensuite bath. The 2 guest staterooms each have twin beds plus a Pullman berth & ensuite bath (head & walk-in shower). Starboard guest cabins have a sliding system to enable the beds can convert from twin beds to a Queen bed.
8 Days/ 7 Nights
From:
$64K +
Kai
70’ | USVI, New England | 6 Guests-3 Cabins
Capt. Justin & Sarah will make sure you leave the Caribbean with an experience of a lifetime. Crew have separate aft crew cabin with head and storage area. Yacht is fully air condition upon request, add $80 per night A/C fee. Yacht has hydraulic swim platform which lowers from the deck into for easy water access.
8 Days/ 7 Nights
From:
$16,000
Vanishing Point
57’ FL, Bahamas, USVI, New England | 4 Guests-2 Cabins
Early Winter based out of Dania Beach, FL for charters in Florida & Bahamas. From January - April 2024 based in the US Virgin Islands. Summer based East Hampton, NY for New England charters. Yacht offers Rendezvous diving only. Crew TBD soon. Captain Only Rate-$18,500 / Or Captain + Chef with 2 Guests: $19,750
8 Days/ 7 Nights
From:
$20,500
Columbia
141' | New England & Caribbean | 8 Guests-4 Cabins
Columbia is ideally suited to up to 8 guests but generally for a 10% premium on the charter rate can accommodate up to 12 guests. Columbia is also available for regatta racing. Dogs are not permitted but occasionally may be considered for a surcharge. Please Inquire.
8 Days/ 7 Nights
From:
$68K +
CAP II
76' | Caribbean & FL | 6 Guests-3 Cabins
You set the pace & itinerary aboard CAP II; your professional, courteous crew will do the rest. Extensively refitted regularly, performance cruiser, CAP II is more than a fantastic sailing yacht; she is luxurious and comfortable, and a joy to be aboard. Very stable, offering her guests a smooth, comfortable ride. It is operated from the aft cockpit, leaving the center cockpit for you to sun, sightsee and enjoy al fresco meals.
8 Days/ 7 Nights
From:
$26,000
Elvis Magic
66' | Antigua, SXM | 6 Guests-3 Cabins
This superb yacht has been meticulously maintained. After returning from Pacific and New Zealand adventures to the Mediterranean Sea, Elvis Magic has recently received major upgrades, new sails, all new AC systems, refrigeration, generator, cosmetics and more!
8 Days/ 7 Nights
From:
$25K +
The Dove
54' | Antigua, St. Vincent, | 4 Guests-2 Cabins
Ocean going cutter designed by WI Crealock and custom built for captain Larry in 1988 and lovingly maintained. Her teak interior is accented by art and curios from Larry's cruises on THE DOVE through the Pacific, South China Sea, Indian Ocean Mediteranean, Caribbean, South America and even the Antarctic.
8 Days/ 7 Nights
From:
$10,800
Eros
115’ | USVI, Newport | 8 Guests-4 Cabins
A beautiful boat, newly refitted with original restored teak paneling. An amazing crew & great meals make for a wonderful vacation. EROS comfortably accommodates ten to twelve guests. Master cabin features a queen bed with ensuite bath including a jacuzzi tub and shower. Fun crew of 5.
8 Days/ 7 Nights
From:
$46,000
Serena
63' | Caribbean | 8 Guests-4 Cabins
Capt. Hugh has returned to the USVI with new 2023 Serena! Hugh started competitive sailing and ocean racing in the UK & France in 1987 (30 years experience). He completed the intensive Royal Yachting Association (RYA) Yachtmaster 300 Ton Sail & Power Commercial License in 2002, and worked as a Captain & Chef in commercial yachting in the Cayman Islands, Virgin Islands, USA & Asia.
8 Days/ 7 Nights
From:
$18,000