Sun, sea, and endless tropical cocktails are what you expect on a Caribbean cruise. But, as Heidi Mitchell learned on a weeklong sailing through the Windward Islands, there can still be surprises in store.

Salt Whistle Bay is one of the most famous and photographed beaches of the Grenadines
Credit: Flavio Vallenari/iStockphoto/Getty Images

Grenada was never on my list. Neither was Martinique. The only detail I knew of the Grenadines was that Mick Jagger had a house somewhere there — maybe on the island of Mustique? To be honest, these particular destinations, part of the Windward Islands in the southeastern Caribbean, seemed vaguely far, immeasurably small, and not entirely worth the multiple flights required to visit from the Midwest. While I like a beach as much as the next girl, a day or two with my toes in the sand is plenty.

Then came my first real Chicago winter and, with it, an insatiable desire to linger in the sun. Around the same time, I learned that you can visit most of the Windward Islands in a week, thanks to the calm Caribbean waters and their proximity to one another. Suddenly they seemed full of promise. I texted my always-keen travel partner, Julianna, and invited her on a weeklong sun-quest aboard Windstar Cruises’ Wind Surf that would begin and end in Barbados and visit St. Lucia; Grenada; Bequia and Mayreau, in the Grenadines; and Martinique.

That the Wind Surf was no typical cruise ship became obvious the instant I clicked my first photo of it in Bridgetown, the capital of Barbados. With its seven white sails billowing in the tropical breeze, the 310-passenger vessel was a far cry from the behemoths that ply the region. At the check-in desk, I sipped a mimosa while scoping out my fellow travelers. That old maxim that cruises appeal to newlyweds and nearly-deads didn’t apply on this small-scale beauty, which felt more like one of those members-only social clubs so popular with Chicagoans during long winters and humid summers. In fact, about 50 of the passengers belonged to a country club in Cleveland; let’s call them middle-aged (which I define as anyone 10 years older than me, in perpetuity). A few families had invited their young-adult offspring. I saw no brides, witnessed only one cane, and spied a smattering of fit passengers — all eager to sign up for diving excursions and morning yoga.

Key cards in hand, we swiftly stashed our suitcases in two 188-square-foot staterooms and made for the lounge chairs on the uppermost Star Deck. As soon as the vitamin D washed over my legs, the serotonin kicked in. Seasonal affective disorder? Gone. The guilt that my husband was toiling away in corporate America? Erased with one sexy photo text. For the next seven days, I’d go on shore adventures and teach Julianna, a cruise skeptic, that small-ship sailing — I’d banned the word cruising — was a killer way to travel to pristine lands that you could barely find on a map.

Julianna was, admittedly, pretty easy to convince. She gleefully swam with turtles on our Sunday snorkeling excursion in tourist-free Martinique. Just as blithely, she agreed to stay on board in Castries, St. Lucia, because she was eager to taste that day’s special dish, courtesy of a new partnership between Windstar and the James Beard Foundation. At the main restaurant, AmphorA, we feasted on grilled guajillo-glazed prawns with charred corn relish and creamy polenta — a recipe from chef Annie Pettry, of Decca in Louisville, Kentucky.

On Grenada, we explored the rugged western coast by minivan, passing red-tiled roofs and crashing waterfalls to reach an isolated beach where glass-bottomed kayaks bobbed in the shallows. Other cruise ships don’t go there; the island was ours and the Granadans’ alone. We hopped in the kayaks and paddled out to a steel-and-cement art installation, Vicissitudes, by British sculptor Jason deCaires Taylor, submerged 15 feet below the surface. As we peered at the circle of hand-holding human forms beneath the waves, I reconsidered the wisdom of downing three glasses of fresh-squeezed orange juice at breakfast. So did Julianna. We hurried back to shore for warm Cokes to settle our stomachs. Funny how clear-bottomed kayaking could make us queasy, but navigating six-foot swells while standing on the bridge with Captain Pedro Pinto was smooth sailing.

The Windward Islands are a subset of the Lesser Antilles, which are surely misnamed. They are Greater, or at least Good Enough, for a day of hanging out on an otherwise deserted beach, reached by tender. On Mayreau, the smallest inhabited island of the Grenadines and the model for any castaway fantasy, we ate barbecue, swam among erosion-smoothed rocks, and posed for selfies with the crew. Continuing that lazy theme on our final day, we did exactly what any true sailors should: stayed on board. Rather than take a tender to Bequia, which is beloved for its hawksbill turtles and stone forts, we opted to bounce on the trampoline floating off the ship’s retractable sea-level platform. As the sails were hoisted, we toasted with champagne cocktails on deck in our bikinis while Puccini’s “Nessun Dorma” blasted over the loudspeaker.

After we’d gone to our cabins to dress for one final dinner, Julianna texted me a photo of a double rainbow, taken from the bridge of the Wind Surf. “And you say rainbows can’t be photographed,” her message read. The images kept coming: a bat made from a face towel, left at turndown. Us chasing a turtle with snorkelers on day one. “I love this ship,” she wrote. “Your cruise-hating compatriot loves this ship.” Of course. I knew all along she’d fall for this roving resort. (Seven-night Jewels of the Windward Islands sailings from $2,199 per person.)