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Stretched out from the northwest corner of the island like a small arm, Pigeon Island is a historical landmark and a satisfying all-in-one nature, beach, and hiking escape minutes from Rodney Bay Marina. The 44-acre mountainous green plot is home to the preserved ruins of British military forts and garrisons; the Brits chased the Caribs out and used the islet to monitor French activity. Walk among the ruins, and hike up to the cannons of Fort Rodney, where the lookout point offers a breathtaking panoramic view of St. Lucia’s coastline and the sea below, dotted with sailboats. Hike down to the beach for a swim and a toast to history at Jambe de Bois, a restaurant on the water.

Rafting on the Martha Brae River—a float down a three-mile segment of the river on a 30-foot bamboo raft—provides a pleasant hour or so in one of Jamaica’s gorgeous ecosystems. Passengers can slip into the water and swim beside the raft, or look for birds in the lush trees along the river’s banks, or just sit back and be carried along. The staging area is 20 miles away from Montego Bay.

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.

One of Bermuda’s most historic resorts—there’s even a 300-year-old sea captain’s cottage on the property—Cambridge Beaches is a traditional rose-hued confection that matches its four pink-sand shores. Though an English country club vibe prevails in many of the public spaces (think tennis whites and croquet on the lawn), the rooms are anything but stuffy, outfitted with vibrant coral and lime-green sofas, zebra-striped rugs, and in some rooms, private plunge pools. Relaxation can be found in the marine-sourced treatments on offer at the Ocean Spa, but if you’re looking to excite the palate, the acclaimed Tamarisk restaurant plates up local takes on creole specialties, from the iconic Bermudan fish chowder to fresh-caught lobster baked in garlic and coconut oil.

Astoria’s Cannery Row has enjoyed a resurgence as a tourist destination for Oregon Coast visitors. As the former state capital clings to the Columbia River with the determination of a stubborn child, dwindling fishery and logging economies give way to opportunities. Bridgewater Bistro pairs perfectly with the new vision for the city’s future. With wonderful water views in a historically inspired space, the Bridgewater is an open and welcoming environment with two levels of seating. Summer sends patrons out on the expansive deck shadowed by the Astoria-Megler Bridge. The menu is focused and locally sourced. Our party started with the Bloody Mary oyster shooters and moved through the salad selection, pausing to peruse the extensive wine list. Local craft beers and specialty cocktails provide plenty of drink options. The main course was split between the fresh salmon and the steak offering, and both were prepared with inspired seasoning. Staff are friendly and professional with a genuine commitment to the work they do. The views have a tendency to distract from the food at hand, but those dishes find a way to hold their own in the competition for a diner’s attention. Combine value, quality, and service in Oregon’s NW corner for a memorable dining experience at the Bridgewater.

A colorful working-class neighborhood near downtown that had fallen on hard times, Woodstock has been revitalized with a mix of galleries, artists’ studios, boutiques, and restaurants. Much of the area’s original vibe remains, however, thanks to the long rows of colonnaded shops that edge Albert and Victoria roads. Among the nearby storefronts that are open throughout the week are Espresso Lab Microroasters and Luke Dale-Roberts’s award-winning restaurant, the Test Kitchen. Continuing down Albert Road, you’ll find spots like the Woodstock Co-op and the very trendy Woodstock Exchange, with a great array of places to eat and stores selling local goods. At the end of Albert Road, there’s a concentration of galleries, including the Stevenson, Goodman, and SMAC. On Saturdays, Woodstock draws crowds to the Neighbourgoods Market, a prepared foods extravaganza in the Old Biscuit Mill.

Straw Hat, on quiet Meads Bay, is an established favorite with over 20 years to its name. Its creative menu of Caribbean cuisine with a twist will have you returning to this beautiful indoor-outdoor beachfront restaurant. It’s the perfect spot for a meal and an afternoon on the sand, or for watching sports. Try the ceviche of red snapper, the bigeye tuna flatbread, or the grilled crayfish with Anguillan rice and peas, among many other picks.

Hop aboard the ferry at Pier 41 in San Francisco, or from the town of Tiburon, and spend a day on the largest and most beautiful island in the bay—Angel Island State Park. You can bring your own bike, or rent one when you arrive, and ride the paved perimeter trail around the 760-acre island. There are open-air tram tours, too, with guides recalling the island’s rich history, as well as guided hikes. Of course, you are free to roam the trails on your own, one of the best of which is the hike up to the top of 788-foot Mount Livermore, where 360-degree views take in the San Francisco skyline and the Golden Gate Bridge. Whatever your plan, know you’ll be immersing yourself in local history in a place that has been a fishing and hunting site for Coast Miwok Indians, a haven for Spanish explorer Juan Manuel de Ayala, and a U.S. Army post starting with the Civil War. From 1910 to 1940, hundreds of thousands of immigrants were processed here, and during World War II, Japanese and German POWs were held on the island. Several buildings and other relics remain as a reminder of the island’s varied history, including the United States Immigration Station museum (open March–October).

Opened at the mouth of the Singapore River in 1928 to celebrate 100 years since Singapore‘s British founding, the Fullerton Hotel was, at the time, the largest and most expensive building in the Lion City. It served as the General Post Office, Exchange, Chamber of Commerce, and Singapore Club before undergoing a $320 million refit to open as a hotel in 2001. Visually, it’s a showstopper, with coffered ceilings, cornices, and marble floors—a Palladian building in stark contrast to the neighboring bland office towers. The atrium lobby is refreshingly bright, with a grandness of scale that brings drama to the arrival experience. Rooms have vanilla-colored walls, and some open to the atrium. The 25-meter infinity pool is almost theatrical, with Doric columns rising behind. Leisurely afternoon tea is a fine excuse to linger in the atrium lobby and appreciate the airy space’s tranquil qualities.

Captain James Cook set up his observatory at Point Venus, one of the loveliest spots on the island. The transit of Venus, which happens maybe once a century, lets observers here see the planet move across the sun. (That’s the official reason for the name, but there’s no doubt Cook’s crew, after months at sea, had a different Venus in mind when they saw Tahitian women.) Now the point’s a windswept corner of the island that feels like there’s nothing between you and another world but the sea. The lighthouse here, Phare de la Pointe Vénus, was built in 1868, 99 years after Cook’s visit.

Originally built to serve the area’s fish canneries, the Historic Requa Inn, at the base of the Klamath River, is one of the few small hotels right near Redwood National and State Parks. You can come for dinner even if you’re not staying at the inn, which is run by a local family. They offer a prix fixe menu Wednesdays through Sundays from April 1 to October 31. The only seating is at 7 p.m., and what you get is a communal, family-style meal: A small group of people sits around a table and shares a selection of seasonal Californian dishes, which are all crafted using ingredients sourced from a nearby organic farm. (Think of it as having dinner with your family, just tastier.) Make a reservation ahead of time, since spots are limited. Visitors can also pick up a picnic lunch here if they order one 24 hours in advance. Although an old establishment, it’s well-kept; guests will find there is no TV or phone in their room, which provides the perfect excuse to sit outside and enjoy the water going by.

Named after its storied sister in New York, this hub of LGBTQI culture on gay-friendly Oxford Street is the only place in Sydney where you can see drag shows every night of the week. Offering everything from stand-up comedy—like the Let’s Talk About Sex show on Friday, where audience members put their “problems” in a mailbox for beloved drag queen Verushka Darling to solve live on stage—to solo numbers and choreographed productions, it’s always a good time. On Sunday, the longest-running drag variety show in Australia, Polly’s Follies, is still being performed after more than 25 years by well-known drag personality Polly Petrie. Pop in on the right night and you might just run into a celebrity like Kylie Minogue or Adam Lambert.

The most important historical site on Guadeloupe’s miniature archipelago of Les Saintes also boasts one of the most breathtaking views in the Caribbean. Perched some 400 feet above Les Saintes Bay, Fort Napoleon’s panoramic view of the water—dotted with sailboats and surrounded by bluffs—is worth a visit to Terre-de-Haut on its own. But it’s of historic interest as well. Rebuilt in the mid-19th century after the British destroyed it, the fort turned into a prison that was used during World War II. It was restored in the 1980s and houses a museum showcasing the history of Les Saintes. You can stroll inside to see the former grounds that served as a jail, and walk the botanical gardens afterwards, filled with the island’s various cactus species. Look out for iguanas peeking out of holes in the fort’s walls, as ubiquitous on the grounds as they are all over the island. Take in the glorious scenery for as long as you like before descending back down, on foot or on your rented electric scooter.

After its previous Vigie location was destroyed by fire, Jacques rose from the ashes at a striking waterfront perch at the entrance of Rodney Bay Marina, a bit removed from the bustle of the other restaurants and bars. As popular as before, the upscale but unpretentious establishment serves Mediterranean and French dishes with a distinctive Caribbean influence to the likes of the prime minister and other high-ranking officials. Chef Jacques offers specialties like pan-seared scallops and red snapper. The veranda setting is particularly romantic at night.

This property is currently closed for hurricane-related repairs.

Peter Island is “an oasis of tranquility,” known as much for its five flawless beaches as its word-class spas and luxurious ocean view villas. The island is the largest of the private islands and the fifth largest of the 60 islands in the BVI. Visitors can hop a ferry to reach the island from Tortola or opt for booking a helicopter, water taxi, or private yacht.