"I regard sea level as the best perspective from which to comprehend island life," writes Jon Bowermaster—who put his theory to the test by paddling the Caribbean's Grenadine Archipelago

St. Vincent on an early Sunday morning. The streets of Kingstown are filled with elegantly dressed men and women headed for church. The windshields of most of the taxis boast GOD IS GREAT decals. But my guide, Rafton "Tall Boy" Cordice, is headed for a different kind of worship, involving an afternoon of rice and beans, rum and Hairoun beer, sunshine and blue seas.

Thanks to an impending hurricane and airline incompetence, I've been stranded here and missing my bags—including my folding kayak—for several days. Tall Boy, who seems to know every last soul on St. Vincent, has turned out to be a godsend, escorting me to the highlights and regaling me with island trivia. The father of twenty—with a full head of black hair that belies his seventy-two years—has been driving me up and down the coast and to the base of the four-thousand-foot La Soufrière volcano, which last erupted in 1979.

St. Vincent is to be my jumping-off point for a kayaking tour of the Grenadines, the thirty-two-island chain at the confluence of the Caribbean Sea and the Atlantic Ocean just north of Grenada. It's a diverse bunch: St. Vincent is home to 100,000 of the chain's 119,000 population and feels like a mini Jamaica; Mustique is renowned as a playground of the rich and discourages mass tourism; Mayreau is the tiniest of inhabited islands, home to fewer than 200 people, a single unnamed village, and one of the most beautiful beaches in the Caribbean; and Tobago Cays' five uninhabited islands are protected as a marine reserve and are famous for having been a location for Johnny Depp and his pirate gang.

Like the tightly bunched British Virgin Islands, the Grenadines—stretching just forty-five miles north to south—are the ideal place for the kayaking adventure I envision: short crossings in the morning, luxuriating on wide powdery beaches in the afternoon, sleeping in air-conditioned comfort. Traveling by kayak requires endurance, patience, and spontaneity. But I regard sea level as the best perspective from which to comprehend island life, and the kayak as the most ingratiating of vessels.

After all the hurricane hullabaloo, Dean passes to the north, ripping through St. Lucia. But still I have no bags, so I leave Tall Boy and board the ferry to nearby Bequia (pronounced BECK-way). Seated under an awning in the back of the boat on an eighty-five-degree day, I am delighted to be out on the water—with or without a kayak.

Bequia is compact, hilly, and covered with bougainvillea, cactuses, frangipani, and oleander. Historically, its industries were boatbuilding, fishing, and whaling, all of which persist to this day. The island's proximity to a migratory path of the humpback made it an important whaling station throughout the nineteenth and twentieth centuries. Today, by agreement with the International Whaling Commission, locals can cull a total of four whales a year, although few hunters possess the necessary skills, which include throwing harpoons by hand from small open boats. On those rare occasions when a hunter is successful, the whale is towed to Semplers Cay for butchering.