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, including our popular BVI charters. Guests aboard this style of yacht will experience the exhilarating thrill of sailing as well as traditional features.

Get started by exploring our popular sailboat picks, 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.

Sailboat Charter 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 Pacific Wave to discover the luxuries, traditional features and romance available on a sailboat charter. Learn more about what the crewed charter experience offers.

Explore the sailboat Pacific Wave

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.

More Affordable Recommendations

Rhapsody: This 74’ Irwin monohull features nautical appointments, comfortable accommodations, plus a wonderful crew team. This owner-version layout features a spacious King Master Suite plus 2 additional Queen cabins. Affordable rates range from $7,200 - $12,000.

Xiuma: This 55’ Oyster monohull features wonderful owners/crew plus lovely accommodations. She can typically accommodate up to 4 guests in 2 available guest cabins including choices from 1 Queen Master, 1 Double, plus 1 Twin. Xiuma may also consider families of 6 with young children. Rates from $6,800 to $9,000.

Verna Breeze: This 54' Lazzara 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 from $6,975 - $8,975. Learn more about Verna Breeze plus view recent comments from guests.

Paradise: This 62' Irwin 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 from $6,990 - $7,775. View recent comments from Paradise charter guests plus learn more about this yacht and crew.

Fidelity: This 45’ Jeanneau monohull features a friendly and flexible crew plus an extensive list of recent upgrades. Her Captain also offers ASA Certified Sailing Instruction. Fidelity can accommodate up to 4 guests in 1 Queen Master plus 1 Queen cabin. Her affordable rates ranging from $5,900 to $7,500 make her a popular choice.

Mid Range Luxury Options

Three Moons: This 72' Irwin monohull provides available on-board spa services, award winning cuisine, plus southern hospitality from her owners/crew. Three Moons can comfortably accommodate up to 8 guests in 4 equal Double cabins. Perfect for couples or families in search of luxury and fun. Rates from $15,000 - $19,000.

Sublime: This 72' Irwin 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 from $14,500 - $18,500. Watch a short video about the Sublime sailing experience to discover the fun and adventure available on this popular yacht.

Pacific Wave: This 72' Giorgetti & Magrini Sailing Yacht features fantastic owners/crew, traditional features, award winning cuisine, plus 2 on-board Dive Masters. She accommodates up to 6 guests in 1 Master aft cabin plus 2 Twin cabins. One of the few traditional sailing yachts featuring a large dinghy with full toy locker. Rates from $16,000 - $18,000. Watch a video featuring Pacific Wave plus learn more about this yacht and crew.

Blue Passion: This 2010 60’ Beneteau monohull features fun yet professional owners/crew, modern and sleek appointments, plus high end offerings. She can accommodate up to 8 guests in 4 equal Double cabins. Rates from $12,500 to $15,000. Blue Passion and her owners/crew won Best Monohull at the 2010 BVI charter yacht show plus Runner Up for Best Monohull at the 2011 show!

Sayang: This 55' Jeanneau monohull features modern appointments and accommodates up to 6 guests in 3 Queens or can be quickly converted to 1 Queen Master plus 1 Queen, making her ideally suited for families of 4 or special occasion charters. Rates from $8,900 - $12,500. Watch a short video plus learn more about this sleek sailing yacht.

High-end Exclusive Suggestions

Takapuna: This 112’ Italian Sailing Yacht features an experienced 5 person crew team, luxurious and spacious appointments throughout, plus sailing performance. Takapuna can accommodate up to 8 guests in 1 Queen Master Suite with his and her baths plus 3 additional Queen cabins which can be converted to Twins on request. All inclusive rates from $45,000 to $52,000.

Taboo: This 85’ Peterson/Aquastar Sailing Yacht features veteran owners/crew, an unparalleled sailing experience, plus plenty of adventure and fun. Taboo can accommodate up to 10 guests in 5 Queen cabins. Perfect for larger groups or families in search of a classic sailing experience. Rates from $24,100 - $29,900.

More Magic: This 2010 67’ Discovery Sailing Yacht features a fun and gregarious crew, modern and luxurious appointments plus space and comfort throughout. She can accommodate up to 6 guests in 1 Queen Master, 1 Queen VIP plus 1 Double cabin. Rates are $22,500.

Tilly Mint: This 2009 67’ Ron Holland Sailing Yacht features a welcoming and friendly crew, lovely appointments plus comfortable accommodations. She can accommodate up to 6 guests in 1 Queen Master, 1 Queen VIP plus 1 Double cabin. Rates from $19,500 - $21,500.

Magnetic Sky: This 2010 70’ Hylas Sailing yacht features a warm and professional crew, modern and sleek appointments plus sailing performance. She can accommodate up to 6 guests in 1 Queen Master, 1 Queen VIP plus 1 Double cabin. Rates from $15,000 - $18,000.

View all sailboats

Sailboat Charter Specials

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

Destinations

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