
Your Perfect Luxury Private Yacht Vacation — Designed for Your Group, Not Just the Yacht
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!

344' Black Pearl Sailing Luxury Yacht
Abide
138' | 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
Eros
115’ | BVI, 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:
$46K +
Optimist
78' | Antigua & Grenada | 6 Guests-3 Cabins
Capt. Ben has been in the yachting industry captaining boats for 10+ years with happy guests. His career started in SE Asia working as a sailing instructor & then as a base operations manager. He sailed the Mediterranean & on to New England freelancing on multiple large sailing yachts in the roles of deck hand, mate & engineer. Currently, he has worked several seasons in the Caribbean & will be joined by a Chef.
8 Days/ 7 Nights
From:
$48K +
Serena
63' | Caribbean | 8 Guests-4 Cabins
Capt. Hugh started competitive sailing & ocean racing in the UK & France in 1987 (30 yrs experience). Both Hugh & Chef are known for their authentic interpretations of the world’s great cuisines – American, Mediterranean, Southeast Asian, and Latin American & signature fusion MediterrAsian cuisine. Two aft queen guest suites accommodate 4 guests. Forepeak cabin is available for a 5th guest. Draft Beer Aboard & automatic Cocktail machine!
8 Days/ 7 Nights
From:
$21,500
Whisper
116' | Leewards-Windward
Full Beam Master with queen bed, desk and settee, 1 Guest Double, 1 Guest Twin. All with Ensuite heads and showers with ample storage. Each stateroom is equipped with bathrobes and slippers, the bathrooms offer hairdryers and a complete range of L'Occitaine products.
8 Days/ 7 Nights
From:
$86,250 +
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’ | BVI, New England | 6 Guests-3 Cabins
Recently refitted, Capt. Justin & Cecil 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. Custom built in 1983 by Wellington Boats Inc. for the then CEO of The CocaCola Company.
8 Days/ 7 Nights
From:
$18,000
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
Sojana
114.73' | Caribbean Leeward | 8 Guests-4 Cabins
SOJANA accommodates up to eight guests in three beautifully appointed cabins, with additional bunks suitable for two children in a smaller cabin. The layout features a forward en-suite master cabin with a queen berth, an aft en-suite VIP double, and an en-suite guest twin cabin.
8 Days/ 7 Nights
From:
$70K +
Dama de Noche
82' | West Med, Caribbean
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. The main cabin has a centerline double berth with a private access to the aft deck. Full hydraulic sail handling with in mast furling.
8 Days/ 7 Nights
From:
$36,750 +
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! Try the latest high-tech water toys like electric Fliteboards — the world’s best e-foils — with two onboard ready for you to glide above the waves.
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











