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This twin-peaked headland—and the ruins of the 18th-century Fort Shirley garrison—preside over Prince Rupert’s Bay, Dominica’s largest wetlands and a docking area for smaller cruise ships. An 1802 revolt here led to the British Empire abolishing all slave soldiers, making this Dominica’s most important historic destination—and now a worthy World Heritage site. A short climb leads to the restored buildings and a splendid viewpoint, complete with cannons. Longer trails spike out into the dry coastal woodlands, populated by crabs and grass snakes (Liophis juliae, known locally as kouwes).

Covering nearly two thirds of Basse-Terre island, Guadeloupe National Park is an astounding 54,000 acres of lush rain forest, plus offshore mangrove and coral reefs. Some of the island’s best-known sights are inside the park, including active La Grande Soufrière volcano at its center, 4,800 feet above sea level. The park also contains famous waterfalls like Carbet Falls and the Cascade aux Ecrevisses, and Les Bains Jaunes thermal pool is a refreshing swim after conquering one the park’s many hiking trails. Nature lovers will swoon over the 800-plus species of flora and fauna here, ranging from orchids to bats to the endangered agouti (a type of small rodent). You can explore Guadeloupe National Park on your own or go with an outfitter like Vert Intense, an eco-friendly operation that knows every inch of this vast green escape, and also offers canyoning.

Kampa, in Prague’s charming Malá Strana district, is Prague’s largest island. Tucked between the Vltava River and the romantic Čertovka channel, the island’s park comes alive in the warmer months with picnickers, dog walkers, and friends gathered on the greenery desperate to catch up on their vitamin D. With direct views of the Vltava’s roaring rapids and the city’s famous Charles Bridge, Kampa is also home to the Kampa Museum, a former mill turned modern art museum dedicated to 20th-century Central European art. Artist David Černý’s gigantic crawling babies are outside the building, while the inner courtyard and galleries showcase other freestanding works, sculpture, paintings, and photographs.

The centerpiece of Turks and Caicos is Grace Bay, on the island of Providenciales (known locally as Provo), where the miles-long sugar-sand shore routinely tops “best beach” lists for the Caribbean and the world. The inland area along this stretch of northern shoreline is where you’ll find most of Provo’s hotels, shopping, and restaurants. Grace Bay is part of the Princess Alexandra National Park. It has calm waters and a sandy seafloor with no rocks or corals to step on, making Grace Bay the perfect place for swimming, splashing along the shoreline, parasailing, and stand-up paddleboarding.

Open from first light until late in the evening, this relaxed bar, just around the corner from La Piazzetta, has an entirely different vibe from the fancier options there. You can have a quick caffè (espresso) standing at the bar with the locals or sit under the striped awning and watch the sunset over the Bay of Naples while drinking a spritz. This bar also serves as one of the island’s best bakeries. Try a flaky breakfast pastry with a morning cappuccino, then swing by later to order a lemon or chocolate version of the island’s famous dessert torta caprese, a flourless cake.

Since its opening along a dazzling stretch of sand known as Cabbage Beach in 1962, The Ocean Club on Paradise Island has been the preferred stay of old-money patriarchs and traditionalists. Though much at the serenely posh resort has remained unchanged, the 105-room property has been modernized to meet today’s standards with spa-sized marble bathrooms, sweeping WiFi, and a restaurant run by star chef Jean-Georges Vongerichten. But it’s the feeling of a privileged, unhurried yesterday that continues to draw an appreciative upper-crust crowd. An on-site tennis pro provides tips for improving your backhand, Versailles-inspired gardens complete with a 12th-century Augustinian cloister offer moments of quiet contemplation, and rounds of golf end with martinis at the resort’s bar. These details, plus knowing that a personal butler and afternoon champagne and strawberries are included in the price, keep guests returning year after year.

Built by Napoleon Lebrun & Sons in 1909, this clocktower landmark was the world’s tallest building until 1913. Its transformation from iconic structure to five-star hotel has brought with it only more reasons to visit, including, first and foremost, the on-site spa—a 39th-floor escape offering build-your-own treatments and a selection of enhancements. Other incentives are the restaurant Clocktower, where chef Jason Atherton delivers Michelin-starred dining by way of updated tavern classics and modern British fare, and the Lobby Bar, which serves signature libations alongside expansive views of Madison Square Park. Once room-bound, it’s easy to stay a while thanks to luxurious details like plush linen sofas, specially programmed iPads, and customized mini-bars.

History, natural beauty, rare wildlife, and luxurious digs are among the charms of Maria Island, a few miles off Tasmania’s east coast. You’ll experience them all during this four-day, three-night excursion across 25 miles of pristine scenery—and fueled by gourmet candlelit dining and fine Tasmanian wines. During the leisurely walk you’ll explore Darlington, a UNESCO heritage-listed convict settlement that once housed 600 prisoners; stroll pristine white-sand beaches; and view the unusual wildlife that calls the island home. At the end of each day, bunk down in one of two secluded wilderness camps, close to clearwater beaches ideal for swimming, and on the last night enjoy the comforts of a restored, heritage-listed home, where you’ll have a celebratory champagne lunch before boarding the boat back to the mainland.

A Carib chief and national hero, Joseph Chatoyer led revolts against British colonists in 1772 and again in 1795. During the latter revolt, his soldiers and their French allies were planning to attack Kingstown from Dorsetshire Hill, but British soldiers marched up from the city and attacked first, killing Chatoyer. Today, he’s memorialized in a monument on that very hill, overlooking the city he fought so hard to regain.

Rum is the Caribbean’s signature spirit, its production documented in the region since colonial times. Just as there are dozens of varieties of rum, Caribbean travelers can select from a wide variety of rum distillery tours. The one offered at Cruzan Rum Distillery highlights the rum-making prowess of the 19th-century Nelthropp family, considered Cruzan rum royalty by many. The Nelthropp family endeavored to craft a spirit incorporating the “warm, tropical breezes that circulate through the open-air warehouses of the distillery.” A sip after your tour will allow you to judge whether they managed to capture St. Croix in a bottle.

St. Lucia’s iconic twin peaks—Gros Piton and Petit Piton—dominate the island’s scenery, soaring 2,500 feet from the sea on the island’s southwest Soufrière corner. Designated a World Heritage Site along with the surrounding Pitons Management Area, these volcanic spires take every first-time visitor’s breath away. There are various ways to experience the Pitons. The brave hike either peak—Petit Piton is more strenuous, and the trail isn’t marked; Gros Piton has marked trails and is a two- to three-hour hike from the village of Fond Gens Libre. Others opt to take it easy and sail past them on a catamaran cruise, or view them from land along the coast or from the terrace of La Haut’s restaurant. Sugar Beach, facing Gros Piton, offers a frontal view of the peaks as you swim.

The Maria Islands—Maria Major and Maria Minor—off the southeastern coast are among the region’s most pristine environments. You can visit the protected wildlife reserve via a 20-minute boat ride from Pointe Sable. On Maria Major, a verdant trail leads you past a variety of unusual tropical flora and fauna, most notably the habitats of six rare native reptile species. Look for St. Lucia’s whiptail lizard and the racer, a nonvenomous grass snake that might appear from a rock crevice. Snorkeling off the beach is part of the experience, too, as the island’s waters are rich with coral reefs. The reserve, a birder’s paradise most of the year, is closed to the public in the summertime to accommodate the nesting season of migratory birds that flock here from Africa.

Nicknamed “the chic boutique,” New To You has been a popular Northern Virginia consignment shop for the stylistic fashionista seeking a savvy bargain for a second-hand Armani, Anthroplogie, Carolina Herrera, Chanel, Hermes, Prada, or another high-end name. Gently worn designer, vintage, and good-as-new clothing, business wear, gowns, shoes, boots, scarves, purses, and jewelry constitute many of the items carefully screened and selected by owner Christine Novak. Strong emphasis on quality, cleanliness, and fit.

Many islands have laws with steep fines against wearing beach wear when not on the sandy shoreline and while you may have heard of folks going au-naturel on St. Martin, that’s certainly not the norm throughout the region. On St. John, however, things were a little different. About a mile walk from a parking lot on the edge of Cruz Bay along what’s called the Lind Point Trail, through typical island bush and over a hill and down through more bush past a fork (where either choice gets you to the same place) intrepid travelers are rewarded with a tiny strip of sand, only around 25 yards long, unofficially known as the island’s only nude beach: Salomon Beach. I’ve been to this secluded sandy alcove a number of times and without fail the maximum number of sun worshipers was never above four or five. In fact, most times, the beach was deserted. So, for years this is where those with a passion for enjoying nature to the fullest could go to let it all hang out in relative privacy… Until recently. Since my last trip to Salomon Beach back in 2007, there’s been a crackdown on this unofficial naturist haven. Suddenly being a free spirit isn’t so free due to the stiffness of fines—around $110 for those caught with their pants down (so to speak). But, hey, doesn’t mean you can’t press your luck!

Around since 1765, the St. Vincent Botanical Gardens claims to be the oldest of its kind in the Western Hemisphere. Tour the gardens with an informative guide, who will point out all the native and exotic plants growing here, including a breadfruit tree descended from the one Captain Bligh brought to St. Vincent in 1793. In the aviary, you’ll also be able to catch a glimpse of the colorful St. Vincent parrot—the island’s national bird.