Sailboats in the 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!


115 ft | 10 Guests in 5 Cabins

Huge amounts of deck space & her very large covered cockpit seats 12 for al fresco dining in addition to lovely lounging areas. Equipped with all the very latest technology, from state-of-the-art sail handling to communications. She is the perfect combination of power under sail.


$52K +


82 ft | 6 Guests in 3 Cabins

An ever timeless SWAN, as the perfect getaway for your dream vacation. With spacious layouts, warm interiors and race-like hull design it offers everything in one package. The crew are capable sailors who work well under pressure maintaining a cool head and are highly organized & personable.


$25K +

Pacific Wave

72 ft | 4 Guests in 2 Cabins

Enjoy Italian luxury on a Caribbean crewed yacht charter while exploring the best of the BVI. Steer a true sail boat between quiet anchorages, sunbathe, dive with professionals in crystal clear waters, then dine on award winning food under the stars. Mark & Lynn welcome you onboard Pacific Wave as Owner Operators & make you feel at home!



Ocean Star

65 ft | 6 Guests in 3 Cabins

A Master King Suite forward & 2 Queen berth suites aft, one of which may convert to a twin-berth suite. "Capt. Hugh & Ellen made my boys feel right at home on the boat. They were up for anything. We set the itinerary together & I was so grateful for their input & willingness to go to places others usually don't!"




55 ft | 6 Guests in 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.




115 ft | 8 Guests in 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.



Raven Claw

82 ft | 6 Guests in 3 Cabins

3 spacious guest cabins. The master cabin offers a double berth offset from the centerline. A private companionway gives access to the aft deck via a sliding hatch. All guest cabins have ensuite showers. A starboard aft cabin has twin side by side berths. The port aft cabin has twin berths + pullman.


$30K +


70 ft | 6 Guests in 3 Cabins

Beautiful Hylas designed by the renown naval architect German Frers. Six guests can enjoy true comfort in three spacious, well-appointed cabins. Each has seven-foot headroom & sound systems. The ensuite master cabin situated aft has a centre-line King size bed 76" long, a settee & a writing table. Your crew will make you feel at home!




65 ft | 6 Guests in 3 Cabins

Master aft full width cabin with walk-around king size ensuite berth. Spacious salon with seating for 6 for formal dining. Extra large cockpit for lounging & alfresco dining. Drop down stern for swim platform. 16' Scuba & Excursion RIB with 70hp engine , WiFi satellite option & lots of Water Toys!




50 ft | 6 Guests in 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.



August Maverick

92 ft | 9 Guests in 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.


$18K +

Dama deNoche

80 ft | 6 Guests in 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 the vacation of a lifetime, every time, aboard this luxury yacht!


$28K +


70 ft | 6 Guests in 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 the water for easy access for guests.




56 ft | 6 Guests in 3 Cabins

Sailing the Grenadines, this yacht combines the benefits of a catamaran with the beauty, grace and sailing characteristics of a monohull. Because she is built with public spaces on the main deck and private staterooms below, she actually fits the space of a 64ft boat into a 54ft boat.




50 ft | 6 Guests in 3 Cabins

Designated to be a fun and active charter yacht, join Odysseus for not only great sailing, but also for onboard diving for certified divers. Guests who are interested will discover a patient instructor and eloquent raconteur.