How to Boat Share Your Next Caribbean Yacht Adventure

The Airbnb concept has come to yacht chartering in the form of GetMyBoat, which connects yacht owners with Caribbean travelers looking to set sail for a few hours, a day, a week, or longer.

GetMyBoat has a database of more than 64,000 boats in 171 countries, including most of the islands of the Caribbean. Available monohull boats and catamarans belong to individual owners as well as yacht-charter companies like Sunsail and Moorings.

Prospective yachties can rent powerboats and sailboats; the site also includes fishing charters, houseboats, jetski rentals, paddle-sports equipment like kayaks, and on-the-water experiences like dive trips and tours. Sleep-aboard experiences are also available as a unique alternative to the traditional Caribbean hotel stay.

Even landlubbers can enjoy a night getting rocked to sleep in a boat docked in an island marina, many of which have an impressive array of services for travelers, such as shops and restaurants. Sailing lessons can also be arranged.

"We have tons of boats in the Caribbean. In fact, the Caribbean is a year-round hot spot for GetMyBoat," says GetMyBoat's digital communications director Kira Maixner. "We even have boats in Cuba."

Spur of the Moment Cruising

Launched in 2013, GetMyBoat previously set a 30-day advance window for rentals, but recently brought that down to 24 hours, so you can easily integrate a yacht charter into Caribbean vacations that also includes stays at land-based hotels and resorts. GetMyBoat offers pay-by-the-day insurance to renters.

Boats can be rented online or via the GetMyBoat mobile app; searches can be sorted by boat size, make, model, type, and desired activity. As with Airbnb, renters have the ability to correspond in advance with boat owners and make payments online; captain and crew can also be booked via the app or website. Geolocation means that you can find the boats closest to your Caribbean island—perfect for last-minute bookings when you have a sudden urge to get out on the water!

The U.S. Virgin Islands, British Virgin Islands, Bahamas, Mexico, and Costa Rica are among GetMyBoat's top rental locations; others in the Caribbean include Belize, Jamaica, St. Maarten, Puerto Rico, the Dominican Republic, and St. Vincent and the Grenadines.

A Wide Selection of Boats

Catamarans are extremely popular for cruising the calm waters of the Virgin Islands, and for $800 a day, you can rent a 43-foot Robertson & Caine leopard cruising catamaran out of Christiansted, St. Croix—split the cost between up to six friends for a great full-day sail. Got the urge to fish? Charter the 53-foot Mystic Man and cast away with up to 12 anglers for $1,000 for a half-day or $1,500 for a full day.

In the Dominican Republic, $169 will get you a dive trip in Punta Cana, while $110 is the tab for a Tortuguero Canal tour in Costa Rica. 

Ready to set sail for a longer journey? Week-long charters of a 51-foot Hanse 505 cruising monohull out of Tortola, BVI, start at $4,250 per week. In the Grenadines, the schooner Heron is available for charters of two days or longer and includes a bit of star power: the boat was featured in the movie Rum Diary, starring as Johnny Depp's yacht in the film based on the book by Hunter S. Thompson.

Other Options

GetMyBoat is just one of many ways you can charter a yacht in the Caribbean. Caribbean beach resorts often contract with luxury yacht owners to provide day trips and sunset cruises for guests, and these boats can also be rented for longer periods as well. At Peter Island in the British Virgin Islands, for example, you can charter the crewed Hans Christian Anderson sloop Silmaril, while at Caneel Bay, the John Alden Skye 51 Spitfire is similarly available for a variety of sailings.

You can book bareback or crewed yachts from other independently operated boats or go through a yacht-charter company like Moorings and Sunsail—the biggest of such companies in the Caribbean—as well as Horizon Yacht Charters, Fraser Yachts, and others.