monohull sailboat crewed yacht charters, catamaran cruises

Sailboat Charters

Sailboat charters provide a classic charter experience and remain a popular choice for our Virgin Island yacht charters. Guests aboard this style of yacht will experience the exhilarating thrill of sailing as well as traditional features.

Explore our extensive list of sailboat charters or contact us to start planning your crewed sailboat vacation.

With Carefree Yacht Charters' insider knowledge and first-hand experience aboard their own crewed sailing yachts in the Virgin Islands, they are the expert source of information regarding sailboat charters.

Why Choose a Sailboat?

Classic sailing experience: Guests aboard these yachts will feel the power of the wind as they enjoy an exhilarating sailing experience.
Traditional features: These yachts offer their guests wonderful character, plus traditional features and amenities.
Owner/Operators: A large majority of our sailboat charters are crewed by the owners of the yacht, which in some cases can provide guests with an added level of attention.

Popular Sailboat Choices (View all options)

Below is a sampling of some of our more popular and recommended picks. Contact us directly to have us guide you through the entire sailboat charter selection process.

Sublime: This popular 72' monohull includes fun-loving owners/crew and an all inclusive dive package. She is ideal for groups of up to 8 guests with 4 equal Double cabins. Rates starting at $14,000. Watch a short video about the Sublime sailing experience to discover the fun and adventure available on this popular yacht.

Three Moons: This 72' monohull provides on-board spa services, southern hospitality from her fun-loving owners/crew, and can accommodate up to 8 guests in 4 equal Double cabins. Perfect for couples or families. Rates starting at $14,500.

Paradise: This 62' monohull offers her guests luxury and space at an affordable rate. She accommodates up to 4 guests in 1 Queen master plus 1 Queen cabin making her ideally suited for families or special occasion charters. Rates starting at $6,720. View recent comments from Paradise charter guests and crew.

Sayang: This 55' monohull sailboat features modern appointments and accommodates up to 6 guests in 3 Queens or can be quickly converted to 1 master plus 1 Queen, making her ideally suited for families of 4 or special occasion charters. Rates starting at $8,200. Watch a short video featuring Sayang to get a feel for this sleek sailing yacht.

Verna Breeze: This 54' monohull offers a fantastic charter package at an affordable rate. Her amenities include gregarious owners/crew, on-board diving, full toy locker, plus spacious accommodations for up to 4 guests in one Queen cabin and one Twin cabin. Perfect for families or special occasions. Rates starting at $5,999. View recent comments from Verna Breeze charter guests and crew.

View all sailboats

Sailboat Charters Specials

Visit our yacht specials page to discover which of our sailboats are currently offering enticing specials.

Monohull Sailboat Experience

The vast majority of our "all-inclusive" crewed sailboat charters include a Captain & Chef, 3 gourmet meals per day, requested beverages, plus standard bar. Watch the short video featuring Sublime below to discover the fun and adventure available on this sailboat charter. Learn more about what the crewed charter experience offers.

Explore the sailing yacht Sublime

Destinations

Consider a sailboat charter in the Virgin Islands, including our popular BVI yacht charters, in and around St. Marten, or the Grenadines, each offering a slightly different flair. Learn more about our Caribbean vacation options.