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ONE LAZY AFTERNOON
, toodling through the magazine rack of my neighborhood bookstore, I stumble upon an intriguing postage-stamp-size classified ad in the back of a yachting rag shelved close to the floor. It reads, “Chocolate delivery vessel, crew needed.” A Web site elaborates: “Prana, the chocolate ship, is a 36-foot wooden ketch that sails chocolate that I make in Grenada to other Grenadine Islands and farther Caribbean islands, too.”

The Grenada Chocolate Company, it turns out, is a tiny producer of two kinds of choco-late bar (71 percent and 60 percent cocoa) on the lush, 12-by-21-mile island at the bottom of the Caribbean. It retails primarily in Grenada, New York, San Francisco, and London. The dreamer who placed the ad and founded the co-op, 42-year-old U.S. expat Mott Green, occasionally sails chocolate himself because, apparently, it’s easier to air-freight bars around the world than it is to find reliable, temperature-controlled shipping to islands just 15 miles away.

Hoo-ha! In my catalog of life’s happy accidents, today’s bit of luck will surely rank high, I predict.

I fantasize about a sweet escape, puttering around dockside markets, doing lazy business, and sponsoring the grandpas playing poker under gumbo trees. I’ll snorkel every morning but never sunburn, and soon share a chocolate bar, Lady and the Tramp style, with a woman who is a cross between a swimsuit model and my kindergarten teacher.

Indeed, the dreams become so vivid and large that they overshadow a gradual, very Caribbean unfurling of reality. When I first e-mail Mott, he cryptically puts off my solicitations. A few months later comes a crushing blow. The “ketch project,” he writes, has been “delegated” to a local named Hope. Pressed, Mott confesses he sold the rotting boat.

For those I’ve seduced with my fantasy, including Sam, a ponytailed 34-year-old buddy who lives on a boat in Key West, this is no reason to let the dream die. Together we hatch a new plan. We’ll charter our own boat, convince Mott to sell us the chocolate wholesale, and keep the goods cool by … well, we’ll sort out that detail in Grenada.

Eleven days later, Sam and I rendezvous in the airport in Puerto Rico.

“It’ll all work out, mon,” he promises.

“Yeah,” I sputter, fully aware that we still have no plan to keep the bars from morphing into hot chocolate. And there’s another teensy problem: We’ll be undocumented workers in Grenada, smugglers in neighboring St. Vincent.

THE GRENADA Chocolate Company looks like a kid’s playhouse—a pastel two-story home high in the island’s rainforest interior, surrounded by banana leaves swaying in the trade winds. When we arrive at three o’clock in the afternoon, Mott, bedheaded and unfresh from a nap but impressed we’ve persevered, shows us around in his boxers.

His factory is one of the few in the world that grows its own cocoa. While roughly 70 percent of the chocolate sold in the U.S. is made by just five companies, which buy beans already roasted by other companies, a small number of artisanal makers roast their own beans (“bean-to-bar”). At GCC, the beans are freshly harvested and roasted on the island. Mott calls this “tree-to-bar” and believes the thundering brownie flavor is the direct expression of the island’s mulchy soil—the terroir, in winespeak. The snobs agree. At London’s Academy of Chocolate’s 2008 awards, the co-op tied French powerhouse Valrhona for best organic dark-chocolate bar.

Mott, it turns out, is a great guy, if a little Motty—passionately scattered. A Staten Island native, he dropped out of college, and then American society, ending up a few years later living in a bamboo hut on a nutmeg farm in the Grenadian bush. When prices for Grenada’s amazing cocoa began declining, in the mid-nineties, he decided to start the co-op.

Together with his partners, Oregonian Doug Browne and local Edmond Brown, he spent three years learning the finicky process of chocolate making—the roasting, shelling, crushing, refining, mixing, and tempering that transforms pulpy fruit into hot liquor and, finally, creamy bars. A lifelong tinkerer, he built whatever small-batch machinery they couldn’t rustle up from European auctions or dusty Jamaican basements. It’s a tidy operation, partly solar-powered and employing just 14 Grenadians and Mott. But it’s profitable, selling about 2,000 organic bars a week.

At the end of the informational tour, it’s business time. Mott’s eyes widen when I place our $1,000 order. But I’ve done the math, and I figure if we buy a grand’s worth for the standard wholesale price of eight Eastern Caribbean dollars (US$3) per bar and sell them to shops for EC$12 (US$4.50) and to individuals for EC$16 (US$6), then we can earn at least 650 greenbacks, enough to cover our on-water costs for the week.

“How are you going to keep it from melting?” Mott asks.

Our two ideas now sound a little impractical: (1) Find a 50-gallon drum, fill it with dirt, and then bury the bars inside—a sort of portable root cellar. (2) Eat them. I mumble something incoherent about coolers, and then gaze toward the sky, where ashen rain clouds have dropped the temp to around 70 degrees, the threshold of solid chocolate. Ten minutes later, 348 bars are snugly loaded into a large TV box, and Mott is waving goodbye, yelling his only instructions: “Sell ’em for as much as you want. Tell me how it goes!”

TRAVEL UPGRADES are usually nice, like a Creamsicle at the gates of hell, but as we discover with Horizon Yacht Charters, they can also totally save your hide. A previous charterer ran the monohull we’d reserved onto a reef, so owner Jacqui has upgraded us to a lavish 38-foot catamaran, with something that Sam has never seen in his 30 years of sailing: two refrigerators! We stack away the 87 pounds of bars like so much gold bullion, snugly filling both fridges, as if they’d come with stickers: PERFECTLY FITS 348 4-OZ CHOCOLATE BARS.

I place the probe of my chicken-roasting thermometer in one of the fridges. This connects to a digital display I’ve mounted beside the cockpit instruments. “Sixty degrees and holding!” I yell to Sam, who’s cracking a beer.

We motor-sail 30 miles into the wind to sleepy Tyrell Bay, on the island of Carriacou.

Our plan is salty simple: The first two days we’ll sail north 80 miles to the island of Bequia, then zigzag back through the sprinkle of islands between Bequia and Grenada, selling chocolate in towns as big as a couple thousand and on isolated palm planters with no more than a fisherman’s shack. In between, we’ll enjoy some glory sailing, the 15-knot winds blowing out of the east allowing us to hot-rod south, the boat knifing through the swell, cockpit fully shaded by the awning, few if any other white triangles in sight.

We hit terra firma feeling—and looking—good. We carry a soft-sided, Windex-blue briefcase cooler from home and wear matching T-shirts emblazoned with the colorful GCC logo, which Mott’s distributor in New York, a dreadlocked Italian Rasta nicknamed Pastrami, helped us create.

Our semi-legit appearances notwithstanding, our reception at La ‘Qua Supermarket is less than enthusiastic. Miss Diana, the large owner of the dimly lit store, wants only milk chocolate.

I pull out a sample bar and let her admire the hand-drawn label of plump cocoa pods before peeling it back to reveal the rapidly melting bar itself. She chews slowly.

“What da deal you do?” she asks.

I tell her our prices as a gaggle of older men draped on a picnic table pass the sample around. Then she produces an Oh Henry! and rattles through a lot of quick, complicated math to show that our dark chocolate—blech—is far more expensive per ounce than her nougaty, milky-yummy Oh Henry!

Sam turns to an old man sampling away: “What do you think?”

“Is pure, good for da heart,” he says, waving the sample at Miss Diana.

She shakes her head in mock disgust, as if to say You can always count on the stupidity of men, and buys a dozen.

Ka-ching!

Throughout the day, Sam and I perfect our hokey good-cop/bad-cop routine—I talk money, Sam gushes sweetness—and the women store owners continue to put us through the wringer, my favorite being Miss Phyllis: “Dis a sample? I don’t like chocolate.” But really, on Carriacou, the chocolate sells itself. Miss Phyllis buys seven dozen.

THE FOLLOWING MORNING, we depart under clouds of meringue on a single tack for Bequia, jamming north-northeast at six knots. In addition to being browner and lower than Grenada, these hillocks belong to our new host country, St. Vincent.

Closing in on the turquoise waters of Bequia, Sam finds St. Vinnie’s blue-yellow-and-green “courtesy flag” in the duffel of supplies provided by the charter company, but he fumbles as he tries to hoist it. We stare, mute, as it flutters away on the breeze.