Bareboating 101: Set a course for sailing adventure

Bareboating 101 Set a course for sailing adventure

A live-aboard sailing vacation offers unmatched appeal. Craft your own itinerary, explore remote islands and spend quiet mornings at anchor with nothing more pressing than choosing the next island to visit.

But it does come with a notable prerequisite: Someone onboard must know how to operate a sailboat. Charter companies require candidates to fill out a sailing résumé, which will help determine what type of boat they can manage.

“Anyone who likes to boat and is comfortable operating boats themselves will enjoy bareboating,” says Melody Delgado of Virgin Island Sailing. “Basically, to qualify, you have to have experience operating a similar powered vessel.”

Those with borderline experience or lacking confidence in their ability can hire a captain for the first day to get acclimated to the vessel and its systems, and get a refresher in managing a boat. Some charter rentals include a captain for up to four hours.

Those with no experience at all can hire a captain for the entire charter for an additional $180-$250 a day, plus room, board and gratuity. Some companies accommodate the sailor wannabe with various levels of sailing classes that cover everything from the rudiments of operating a vessel to offshore, “bluewater” sailing.

“In choosing a type of boat, it depends on how many people are in your charter,” says Beth Weinstein of The Moorings, a leading charter company. “For couples or families, catamarans have more spacious berths, more en-suite baths and more living space below and on deck to enjoy.”

Monohull sailboats have been the workhorses in traditional charter fleets, but catamarans have had a surge in popularity. Multihulls now make up about 35% of wordwide charter fleets.

But for the traditionalist and the adventurous who don’t mind life on the tilt, monohulls still win the day.

“Adventurers should choose a large monohull,” Weinstein says, “to get that feeling of slicing through the water and bringing out their inner sailor.”

Weinstein cautions that everyone coming along should share the same expectations and the overall plan for accommodations, activities and, especially, the sailing destination.

“I think it’s good to choose a destination you really want to see at the end of the day,” Weinstein says. “It’s the experience you are paying for.”

Cathy Parsons of Medford, Ore., who has chartered in the Abacos, British Virgin Islands, Grenada and Tahiti, agrees. “For us, the first thing we look at is if we can get there easily,” Medford says. “We don’t want to spend three or four days on a plane.”

Parsons looks for areas that have many islands close together for easy island-hopping. She also identifies an ancillary benefit to sailing: “It’s a chance to get the kids away from the electronics and get some rich family time.”

We’ve rounded up a trifecta of sailing regions perfect for a bareboat vacation.




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