Cruising in the Caribbean means many things to different people. For some, it means hopping on a megaship and signing up for rock climbing on the stern of the ship while it meanders on to the next port of call. To others, it means sampling onboard restaurants while coordinating sightseeing excursions and duty-free shopping.

But if you are a sailor, it means looking for a charter company that will offer you a sailboat you can skipper yourself, while personally navigating choice islands with low-key anchorages. My husband and I recently returned from a sailing vacation in the Windward Islands that also offered us a chance to earn two of the three certifications needed to charter a boat anywhere in the world.

Additional Photos

Tim Reardon, the author's husband, and Miriam Gough pose with Seymour, the skipper at the Barefoot Charters sailing school.

This notion of chartering a sailboat in the Caribbean came about a couple of years ago, when we traveled to Grenada, the southernmost island of the Windward chain. We originally traveled there to take a Windjammer Cruise, but when it was canceled, we decided to go to Grenada anyway and found an all-inclusive resort with a fantastic beach, facing all the sailboats passing by our lounge chairs on the beach.

Once we realized this region was home to some fabulous sailing grounds, we felt bound to return and spent months reading about the best places to charter. We narrowed it down pretty easily, having found a company affiliated with the American Sailing Association called Barefoot Charters, which has been in business for 27 years, successfully selling charters and providing instruction along with certifications.

It seems that most ASA schools will design a program for your particular needs, but if you prefer, you can purchase a pre-planned itinerary. While previous sailing experience is not necessary, it certainly makes it easier to pass at least the first two courses in about five days. Another great feature is that you can opt to pre-purchase provisions (food and paper products) for your boat, which cuts down on departure time when you arrive at your vessel.

We chartered a 34-foot Jeaneau, which is a sailboat close to the size of our own, so that we could adapt to it faster.

The itinerary we selected allowed us to sail at least for four to five hours each day, visiting some very private islands in the Grenadines including celebrity-inhabited Mustique, known for its upscale properties, pricey moorings at $200 for three nights and the infamous Basil’s Bar, billed as one of the top 10 bars in the world.

Another island grouping on our schedule was Tobago Cays, which are uninhabited, yet seemed to be the most popular among all the places we visited and offered a protected area where we could snorkel with some of the largest turtles I had ever seen.

Most of the islands in the lower Grenadines have private homes for rent, small B & Bs or exclusive resorts. We managed to see Palm Island, Petite St. Vincent, Petite Martinique, Carricou, Union and then had a lunch stop at the Whistle Bay Resort in Mayreau. We could also catch a few glimpses of Grenada in the distance, just past Carricou. As we sailed down and around these islands the swells that tossed our boat around reached 8 to 10 feet in height and knocked us around from every direction. The waves were crashing over the deck, making the journey quite exciting!

As we began our return to St. Vincent, our original port, we made two last stops, one at Canoun, known for it’s upscale Trump Resort and then finally on to Bequia. About three hours into our trip to Bequia, we were greeted by a pod of dolphins that swam alongside of our boat for about 10 minutes, then headed off to follow the current.

Pulling into Elizabeth Harbor, we practiced man-overboard techniques, which is a requirement for part of our certification. It took us three tries to snag the floating fender, so with practice we greatly improved and can reassure our family and friends at home that we are now better prepared to pick them up should they fall into the chilly waters when sailing with us in Maine.

Bequia is a lovely island with a delightful harbor walkway filled with plenty of choices for outside dining in full view of the ferries coming and going, the sailboats reaching their moorings for the night and the inflatables buzzing back and forth. While this is a beautiful spot to visit, travelers to this area should realize that it is not the typical tourist destination and there are few places that cater to souvenir shoppers anywhere along this route.

One last word of advice: For anyone contemplating this type of vacation, I would highly recommend checking out the services offered by a travel agent, as they can sort out many of the complexities involved in booking multiple airlines, distinguishing among sailing programs and helping to alter schedules when both man-made and natural disasters interrupt your travel plans.

Perhaps it is obvious why we opted to take only two of the three required tests on this trip, but just in case it is not, we did this on purpose — mainly so that we would have a good excuse to return and take part three to become fully qualified to charter our own sailboat anywhere in the world.

We are making plans to revisit the Caribbean and enjoy the challenges of sailing, living aboard and studying. In the meantime, we are out on Casco Bay on our own 31-foot sailboat, practicing what we learned.

Miriam Gough is chairwoman of the Travel and Hospitality Management department at Kaplan University/Maine.

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