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For those who aspire to travel as trendsetters in Jamaica, it helps to know that Port Antonio, way out on the eastern end of the island, is the destination to head for. And the address to shelter at is the Trident Hotel, whose 13 waterfront villas would not look out of place on South Beach. Nor would the crowd that hangs around its infinity pool or in its restaurant, Mike’s Supper Club, where local musicians and the occasional celeb sit down to knock out tunes on the 1917 Ferrari-red grand piano. The Trident Castle, a kind of fantasy annex, is a former private residence whose grand rooms, sea-view terraces, and dollhouse-size chapel make it ideal for destination weddings. A hard road to get there? Not for guests who avail themselves of the helicopter pad.

When Antonio Marras opened his first showroom and concept store in a residential neighborhood, fashionistas didn’t flinch at making the 10-minute taxi journey from downtown. The Sardinian designer of women’s clothing has earned a following for his fashion-forward style that avoids trends. His collections run the gamut from casual ribbed tanks with hand-sewn sequined flower patches to special-occasion silk jackets and dresses embroidered with Swarovski crystals. Couches and a menu of wine, coffee, and Sardinian sweets invite lingering. Via Cola di Rienzo 8, 39/02-7628-0991. This appeared in the October 2013 issue.

Stroll inside the Errol Flynn Marina, located right in Port Antonio town, for a waterfront respite along manicured lawns and sailboats. Enjoy an afternoon “I-Scream” cone from the on-site Devon House, a household name in Jamaica. There are public benches by the water, as well as bars and restaurants. If you can, stay long enough to enjoy the sunset.

It’s small compared to other capitals, but Panama City’s historical role as a port and part of a canal that brought together people, commodities, and customs from every corner of the planet endows it with a cosmopolitan air. Come visit a tiny giant.

What could an Alaska local ever discover on a voyage through the Inside Passage? Just the essence of the place he thought he knew.

An amateur baker apprentices with a Paris boulanger and learns the secret of artisan bread.

After strolling Storm King Art Center or DIA Beacon, Tarry Lodge is the perfect stop on your way back to New York City. Mario Batali opened it up as a neighborhood restaurant for the Port Chester crowd and a go-to for out-of-town Manhattanites who love his Italian comfort food. Don’t miss the clam, chili, and oregano or pistachio and goat cheese pizzas. Waits can be long so if you’re trying to beat traffic just get take out from their curbside service.

A journey through one of the world’s last, best travel secrets.

This tiny hideaway overlooking the sea near Port Antonio originally served as a live-in recording studio for performers such as No Doubt, Alicia Keys, and Amy Winehouse. Although recording sessions still go on, Geejam is now a seven-room hotel, its guests often honeymooning couples acting out fantasies having nothing to do with rock and roll. Geejam’s cabins, especially, are very private, and guests sometimes spend days taking meals on their veranda and splashing in their outdoor Jacuzzi without being seen by anyone but the staff, who appear only when called. Of course, who wants to stay hidden forever when the Bushbar restaurant promises convivial chitchat, an occasional game of pool, and even live music? Not to mention that the hotel beach, in a cove across a road at the bottom of the property, promises four-poster sunbeds and, yes, Wi-Fi.

A writer seeks out the disappearing workshops that have been the source of elegance in Naples for generations.

Charlotte Amalie is the capital of St. Thomas, and Frenchtown is a settlement just to the west of the capital. The name St. Thomas is rooted in the Dutch word Taphus, meaning “beer halls”—stemming from this once notorious port’s reputation as a lair for pirates and scoundrels. The name still fits these days, albeit not so scandalously, in Charlotte Amalie.

Québec’s hotels range from repurposed historic buildings in the Old Port to country retreats and grand dame properties overlooking the St. Lawrence. Unique amenities (like fireplaces, restaurants helmed by notable chefs, complimentary cars) are also de riguer.

From refined and stylish hotel bars to rustic neighborhood tascas popular with students and workers, we’ve rounded up Lisbon’s best places for sipping port, beer, tea, coffee, and vinho. We’ve found the best bars, cafés, and terraces to drink in this hilly Portuguese capital.

This stunning white-sand stretch, just a five-minute drive east of Port Antonio, is the only beach in Jamaica with waves high enough to surf. Boston Bay is also one of the few remaining public strands on the island. It continues to attract more locals than tourists and as such is nearly vendor-free. You can watch kids splashing about on their boards, or you can rent your own for a Surfing 101 lesson. Be forewarned: As at many beaches, sometimes the waves are flat, but you can console yourself with a short stroll down the beach to the famous Boston Bay jerk chicken stands.

There’s no shortage of refreshing waterfalls in eastern Jamaica. But after Reach Falls, I’d say Somerset—also located on the east coast—is a close second in natural beauty. Somerset Falls’ cascades can be reached by hiking or by canoe ride along the river. Either way, it’s a stunning, still relatively verdant area teeming with bird life—resident parrots—and caves to explore. It’s easy to find too, ideal for a day trip from either Port Antonio or Ocho Rios. Look out for a billboard right off the paved northern highway, about an hour and a half north of Ocho Rios.