How To Plan A Bareboating Adventure in the Caribbean

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.

Planning a Bareboating Vacation

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."

Tips for a Bareboating Vacation

My friends and experts in the business offer these tips for a successful bareboating vacation:

1. Check out sailing classes ahead of time through community education or local marinas. Learning to anchor and dock a boat, along with tying a few simple knots, will go a long way in preparing you for a week captaining your own boat.
2. Although it’s not entirely necessary, purchase a set of navigational charts and a Cruising Guide of your destination by Cruising Guide Publications. These will help you become familiar with the area, offer advice on where to anchor and what to see in each destination.
3. Decide how much you want to cook and eat on board and how much you want to motor in to a beach bar or restaurant. Ordering too many provisions is a common mistake by first-timers. Most marinas have supplies you can pick up along the way.
4. Most marinas also have a shower and good restroom facilities for those chartering their own boats. Most boats also have fresh water showers on the back of the boat. Otherwise, a marine toilet will probably be the only unpleasant part of your accommodations.
5. Shorts, t-shirts and flip-flops are just about all you need. Over-packing is another common mistake. And travel with soft-sided luggage so that it stores easily in your cabin.
6. Plan to be at your destination for the night by no later than 4 p.m. As the sun lowers on the water, anchoring becomes a little more difficult for those not proficient in this necessary task.
7. The off-season is always going to be cheaper for any travel in the Caribbean.
8. Insurance will be offered through your charter service but do your homework. Look for travel insurance that covers the concerns of the consumer of these independent types of vacations.

Would you ever consider renting your own boat for vacation?

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