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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.

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.

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.

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).

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.

The home of St. John Brewers, among the leaders of the recent craft-beer revolution in the Caribbean, is a must-stop for all beer lovers visiting St. John. At the Tap Room, you can sample the brewery’s very latest beers, sometimes even while they’re in mid-development. Look for a plain black tap among the lineup of more colorfully ornate ones behind the bar. New beers in development are often available there. Feedback from customers goes into finalizing the brews.

La Fosca is one of the most popular beaches around Palamós. It’s a five-minute drive or a 20-minute walk north of the town’s marina. The sandy interior of the cove is divided by a rocky promontory in the middle, while the ruins of the Castle of San Esteban de Mar are at the north end of the bay. During the busy summer months, there are ample services available at La Fosca, including lifeguards, seaside restaurants, bathrooms, showers and beach-chair rentals.

A visit to the incredible 365-island archipelago (also called the San Blas Islands) within the communal lands of the Guna Yala indigenous nation provides some extraordinary seaside experiences. The islands making up the outer archipelago are unspoiled and feature gorgeous white-sand beaches, turquoise seas, and a one-of-a-kind encounter with Guna culture. Visitors lodge in natural-material huts (cane walls and interwoven palm-frond roofs) or—if you’re in the mood—sleep under the stars in palm-strung hammocks. Local women sport colorful dress made in the style known as mola, a traditional Gula artisanal weaving technique. A highway was built several years back that lets you travel from Panama City to Puerto de Cartí in as few as two hours.

Designed by Danish architect Jørn Utzon, the Sydney Opera House was inspired by its dramatic setting on Bennelong Point in Sydney Harbour, a location that’s long been sacred to the native Gadigal people. While construction took 16 years, including four years to figure out the spherical solution to the icon’s soaring sails, any controversies melted away when the masterpiece was completed in 1973. The same outside-the-box thinking that built the shell-shaped sculpture seeps through its walls today in the form of boundary-pushing opera, theater, and dance as well as contemporary music and mind-opening lectures. The landmark is also home to the beloved Opera Bar and Bennelong Restaurant upstairs, where diners can eat pavlova shaped like the landmark in which they sit.

Vancouver’s most famous urban space, the thousand-acre Stanley Park, epitomizes everything that locals here love about the outdoors, and visitors have many ways to explore the expansive grounds. Hiking trails weave around totem poles and hemlock trees, while at the beaches, you can swim, people-watch and picnic. Rent a bike or a pair of in-line skates for a scenic ride along the Seawall, or wander through the many gardens where rhododendrons, azaleas and roses bloom.

When it comes to beach bars, it doesn’t get much better than this open-air spot on picturesque Cockleshell Bay. During the day, guests can take advantage of lounge chairs, beach volleyball nets, and snorkeling gear rentals. Friday nights bring bonfire dinners, while Sunday afternoons feature live bands and dancing. The menu is heavy on seafood prepared in the traditional Caribbean way, with popular dishes ranging from corn chowder to coconut shrimp and conch fritters.