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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!

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Sailing Yacht Charter Monohulls in the Caribbean Virgin Islands

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 +

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Sailing Yacht Charter Monohulls in the Caribbean Virgin Islands

Savarona

93’ | Caribbean Leeward/Windward | 6 Guests-3 Cabins

Built in 2001 & always kept in meticulous condition. With a recent extensive refit; new hard dodger, convertible Bimini new deck, exterior paint, new toilets, new AC, new generator, engine, new rigging, standard hatches replaced with flush, new Miele stove & cook top, New B&G H5000 electronics, extensive varnish work carried out throughout the yacht, new upholstery & bedding throughout, new deck canvases, new Doyle ICE fiber sails 2016.

8 Days/ 7 Nights From:

$35K +

Sailing Yacht Charter Monohulls in the Caribbean Virgin Islands

CAP II

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. Great crew this season!

8 Days/ 7 Nights From:

$23,000

Sailing Yacht Charter Monohulls in the Caribbean Virgin Islands

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:

$16,900

Sailing Yacht Charter Monohulls in the Caribbean Virgin Islands

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:

$44,000

Sailing Yacht Charter Monohulls in the Caribbean Virgin Islands

August Maverick

92’ | 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. You’re in good hands with owner Capt. Shawn! He holds a Bachelor's Degree in Naval Architecture & Marine Engineering from the U.S. Coast Guard Academy. He is also a PADI Dive Master.

8 Days/ 7 Nights From:

$34,000

Sailing Yacht Charter Monohulls in the Caribbean Virgin Islands

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:

$10,700

Sailing Yacht Charter Monohulls in the Caribbean Virgin Islands

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:

$18,500

Sailing Yacht Charter Monohulls in the Caribbean Virgin Islands

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 +

Sailing Yacht Charter Monohulls in the Caribbean Virgin Islands

Arrow

80’ | Grenadines | Antigua | 8 Guests | 4 Cabins

Very hard to find in a monohull: 4 Equal-Sized Double Cabins! All have ensuite baths & A/C. The main saloon is very spacious with comfortable seating and a large dining table. On deck there is plenty of space for sunbathing and seating for 8 around the cockpit table. She cruises at 8 knots under power but has reached speeds of 15 knots under sail. The stern transom folds down to provide an ideal swimming platform.

8 Days/ 7 Nights From:

$27K +

Sailing Yacht Charter Monohulls in the Caribbean Virgin Islands

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:

$20K

Sailing Yacht Charter Monohulls in the Caribbean Virgin Islands

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

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