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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!

Tell Us What Type of Yacht, When and Where You Want to Charter!

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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 +

August Maverick

92 ft | USVI | New England 6+ Guests-3 Cabins

Elegant and classic AUGUST MAVERICK is a family friendly charter yacht offering a crew of 3 for inclusive and captain only charters in the Virgin Islands as well as New England. Offering many options & combinations of cabin use due to flexibility of the crew.

8 Days/ 7 Nights From:



70 ft | 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:



55 ft | BVI | 6 Guests-3 Cabins

Your crew is multilingual (English, French, German & Italian), their backgrounds ranging from marketing management to teaching music. Built in 2005, it is air conditioned throughout & maintained in an immaculate condition for your maximum comfort & safety.

8 Days/ 7 Nights From:



115 ft | 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:


Dama deNoche

80 ft | Caribbean | Italy | 6 Guests-3 Cabins

Dama de Noche is a stunning Oyster 82 luxuriously appointed with teak planked soles and neutral soft furnishings including leather giving a light and airy and contemporary feel to the interior spaces. Warm hospitality will guarantee you a luxury sailing vacation of a lifetime!

8 Days/ 7 Nights From:

$32K +

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:


The Dove

54' | Antigua | 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:



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 +


76' | Caribbean & FL | 6 Guests-3 Cabins

Performance cruiser, CAP II is more than a fantastic sailing yacht; she is luxurious and comfortable, and a joy to be aboard. She is operated from her aft cockpit, leaving the center cockpit for her guests to sun, sightsee and enjoy al fresco meals. Does not charter in US waters.

8 Days/ 7 Nights From:


Emily Morgan

57' | Caribbean | 8 Guests-4 Cabins

Primary cabin is aft & full beam of the yacht with a king size bed. A guest cabin aft of the salon & forward of the master cabin, has side by side twin beds & shares the facilities with the master cabin. Forward of the salon, 2 mirror image cabins on the port & starboard side, have a lower single bed & upper Pullman berths. The 2 forward guest cabins have shared facilities with the crew.

8 Days/ 7 Nights From:



50 ft | USVI | 6 Guests-3 Cabins

Antillean sports four cabins, three for the guests and one for the crew. Each is completely self-contained, and has its own facilities. Diving Available Onboard! 2018 refit: hull repainted, new cushions made for the cockpit and deck, a new Bimini and dodger, teak refinished.

8 Days/ 7 Nights From:


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