Dreaming of a Caribbean vacation during the cold months of winter is as common as the common cold for anyone who lives north of the 28th parallel, which is basically Tampa, Florida. With so many great islands, beaches and resorts, it’s a tough choice, but how about throwing out those options and throwing your sails to the wind – literally.
Bareboating is an exciting and adventurous way to explore many of the Caribbean islands at a speed that’s no greater than the balmy breeze itself. Instead of a big cruise ship or planting yourself on one beach for a week, bareboating is when you become captain of your own vessel for the duration of your trip. Explore lots of beaches, restaurants and sites at a pace you set for yourself.
Most operators require some sort of sailing experience from those they rent to, or at least the ability to dock and anchor the boat. If the operator is not comfortable with your skills, or you are not comfortable with your skills, you can hire a captain for a portion or the entire trip.
That’s what past sailors I know did on their honeymoon. When he was a teenager spending summers in Hawaii with his father, my friend became a fairly accomplished sailor. Despite that expertise, he decided they would hire a captain for the first three days of their week-long adventure to make sure they were both comfortable with the boat.
They began their research at a New York boat show months before, talking with a number of travel agents and charter companies. The British Virgin Islands, because of the prevailing southeasterly winds, is considered one of the easiest places in the world to sail.
"We were never really out in the open ocean and could always see land," my friend said. "It would have been possible to simply motor everywhere we wanted to go without ever raising a sail."
The couple chartered a 40-foot monohull for their honeymoon. On another trip a few years later, they chartered a catamaran and decided they enjoy the catamaran more.
"When cooking on the monohull, you have to keep your eyes on everything because the boat rocks a bit more," the wife said. "Cooking on the catamaran was so smooth it was like cooking in our apartment in New York."
Another couple has bareboated in the Caribbean three times, twice in the BVI and once in St. Vincent and the Grenadines.
"The Frances Drake Channel is dotted with all of these little islands, each one with a beach bar or marina where we have lunch and listen to music," my friend said. "We like the pace and the ability to experience a lot of different places on one vacation."
Both couples have experienced a few minor engine problems during their vacations, but radio access brought assistance from the charter company in a short amount of time. The only negative one couple experienced was in the Grenadines when locals approached their boat trying to sell trinkets or services.
"That’s against the law in these waters," he said. "We knew that from reading the Cruising Guide and all we did was threaten to take their pictures and report them to the police and they left us alone."
My friends and experts in the business offer these tips for a successful bareboating vacation:
Would you ever consider renting your own boat for vacation?
Note: Available plans and coverages may have changed since this blog was published.
Arch RoamRight recently launched two plans on our website; learn the differences between the plans.
Volcanic eruptions are natural disasters that may be covered events under Arch RoamRight travel protection plans. From minor disruptions to catastrophic events, volcanos can affect travelers around the world.
A Midwest farm girl at heart, Diana Lambdin Meyer caught the roaming bug early in life. Diana married well - to a photographer who also has the travel bug and whose work in still and video complements her words. Now based in the Kansas City area, Diana is a member of the Society of American Travel Writers who makes a full-time living on the road and at the keyboard. Read about Diana's adventures on her blog, Mojotraveler or follow her on Twitter or Google Plus.
Travel smarter with travel insurance from RoamRight. Get your free, no-obligation quote online today.
View all Blog Authors
View Countries with Blogs
Sign up for RoamRight's FREE monthly email newsletter to get travel tips, tricks, news, ideas, and inspiration!
The RoamRight mark is used by Arch Insurance Company and owned by its parent company, Arch Capital Group (U.S.). All insurance products are offered and underwritten by Arch Insurance Company. The term "Partner", as used on this website refers to any unaffiliated third party entity that may offer or disseminate Arch RoamRight travel insurance. The term has no legal meaning whatsoever and Arch RoamRight hereby disclaims any such legal meaning that may be ascribed to it. Click here for privacy notice.
Copyright© 2020 Arch Insurance Company. All rights reserved.