T+L navigates the Caribbean the old-fashioned way: by billowing sail on small-ship cruises.

Credit: Andrew Rowat

The first indication that this is not your typical Caribbean cruise: the climb up a rope ladder to a perch known as the crow’s nest, a necessary part of regular crew operations that’s offered here as passenger entertainment. The second: the widow’s net that serves as a kind of nautical hammock, slung from the ship’s bowsprit, stretching over the indigo sea.

I am aboard the 170-passenger Star Flyer, a replica of a 19th-century tall ship that is one of three owned by Star Clippers. There is no waterslide, no formal night, and no children’s program. Most of our ports of call are at quiet beaches for a few hours of snorkeling and windsurfing; only one involves a gauntlet of jewelry stores. The “spa” is a simple, open-air hut with a Balinese mat and Thai massage treatments. But perhaps the biggest tip-off that this isn’t your standard cruise is that in our seven days at sea, we’re actually sailing—thanks to the 16 sheets atop our four-masted clipper—more than 300 miles, from St. Maarten through the British Virgin Islands, on to St. Kitts and St. Bart’s.

In a nod to Robert Louis Stevenson, Star Clippers has dubbed this the Treasure Islands itinerary: Norman Island, one of our beach stops, is said to have inspired his tale of pre–Johnny Depp pirates and an X-marks-the-spot map. It’s an authentic journey, fueled by the trade winds that sweep us across the waves.

That we’re powered by wind is rarer than you might think. Many ships hoist the canvas for show; on others, crew members push a button to raise sails above vessels that are more floating hotel than schooner. Some never raise them at all. What Star Clippers offers is true sailing, with ropes as thick as your arm, braided through blocks and around winches (granted, they’re electric), neatly coiled by sturdy crew hands and looped on stanchions.

Sail-away is a ritual established our first evening as the ship departs from the cruise dock in St. Maarten. Wine glasses in hand, passengers settle on the top deck. As the canvas rises against a full moon, Vangelis’s theme from 1492: Conquest of Paradise sounds from the speakers. In lesser hands this moment could be saccharine, but I find it surprisingly heart-swelling.

Days take on an easy rhythm. Breakfast and a briefing (in three languages, no less) by our twentysomething Danish cruise director, Philip. After a few hours’ voyage to our next island, we take tenders—small dinghies, really—to a beach that would otherwise be inaccessible on a large ship.

This is sailing with comforts. Cabins feature duvet-topped beds, marble bathrooms (some with whirlpool tubs), and in-cabin televisions with DVD players. Two plunge pools and an overly air-conditioned library we dubbed the Icebox provide refuge from the heat. Dinner is an ever-changing five-course menu: watermelon sorbet; tropical ceviche; rack of lamb; bouillabaisse; grilled Caribbean lobster; and local hot sauce from Grenada. A daily buffet lunch is served on board, but many passengers prefer to dine at waterfront shacks like the one on Norman Island, where a good-natured woman behind the bar whips up a frothy lemonade that’s not on the menu.

To handle the social end of things, the maître d’ works as deftly as a matchmaker, mixing tables of unfamiliar groups who speak the same language. The first night we’re seated with June and Bill from Ireland (his grandfather worked in the yard that built the Titanic) and Chris and Sue, a housing developer and health official from England. Other evenings we’ll sit with a naval economist, a rare-book seller, a real estate investor, a pair of college professors, and a doctor traveling with her teenage daughter.

On Anguilla, we ride to shore via tender, then wander up the beach to Johnno’s, a bar adorned with posters of Ella and Miles. A makeshift band tunes up; a local singer pours out a moody rendition of “Misty” (the clarinet player turns out to be Larry, a fellow sailor).

Virgin Gorda brings one of the trip’s few organized excursions, to an eerie beach boulder field known as the Baths. The nearby island of Jost Van Dyke has what may be the most beautiful of the beaches of the trip; by afternoon it’s also the most vibrant, thanks to the rum Pain Killers that flow nonstop at the Soggy Dollar Bar.

Our arrival in St. Kitts comes nearly five hours later than scheduled, due to strong headwinds. To fill the time, the sports staff—a trio of Scandinavians who look like they’ve stepped out of an Abercrombie & Fitch catalogue—arrange a “deck golf” tournament, a spirited contest involving a wooden mallet, a flat puck, and chalk-drawn sea monsters guarding the “holes.” Equally quirky: the cheeky guest-and-crew “fashion show,” which defies real description (hunky dive-master Martin is a standout in a terry sundress).

There’s a retro quality to all this. Then again, it’s a yearning for a simpler, back-to-basics experience that has brought us on this cruise. If there’s an effective antidote to our Twitter-crazed lives, this may be it.

The winds eventually lead us to St. Bart’s. A few fellow passengers head off for adventure tours above and below the sea, but most of our group choose to soak up the stylish insouciance of Gustavia, admiring the friendly French bulldog lazing outside the Vuitton shop and nibbling on steak frites at a bistro in town.

But nothing can compete with our final evening at sea. As everyone gathers on the top deck for sail-away, champagne in hand, the silver-haired captain blows a wistful tune on his bagpipes to mark daylight’s end.

Starclippers.com; seven nights from $2,033 per person. This season, the Star Flyer’s identical sister ship, the Star Clipper, is sailing the Treasure Islands itinerary.

Paul Gauguin Cruises Foodies rejoice: Gauguin’s new ship, the 90-passenger Moana, makes local ingredients a focus. pgcruises.com; seven nights from $2,595 per person.

Regent Seven Seas Cruises Truly all-inclusive, from the top-shelf liquor to the unlimited shore excursions at every port. rssc.com; seven nights from $4,149 per person.

Seabourn Suite ships (from 208 to 450 passengers) call at the less-visited harbors of St. Lucia and Jost Van Dyke. seabourn.com; seven nights from $2,499 per person.

Seadream Yacht Club With up to 112 guests, it can feel like you are on a friend’s mega-yacht. seadream.com; seven nights from $2,499 per person.

Silversea Cruises Explore hidden gems of the Caribbean (Cartagena! Huatulco!). silversea.com; seven nights from $2,250 per person.

Windstar Cruises Revamped sailing yachts bring up to 310 passengers to major and minor ports. windstarcruises.com; seven nights from $1,599.