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A short walk from the city center, Koombana Bay is famously frequented by cavorting bottlenose dolphins; in its calm waters, you may even find yourself swimming right next to one of these remarkable creatures. The wide, white-sand beach is easily strollable, with views of boats from the nearby Koombana Bay Sailing Club. Beach volleyball is a big sport here, and the restaurants and cafés of the nearby Marlston Waterfront are popular with both locals and visitors.

Although Chile’s central coastline boasts a string of attractive beaches along with towns filled with visitors seeking relief from the heat, the truth is the water is freezing cold year-round due to the Humboldt Current that brings Antarctic water up the coast. You’ve got to go pretty far north to find temperate seas. Bahía Inglesa is a stretch of coastline where the turquoise waters are tranquil, the sand is white, and there are dozens of beaches—some are along waveless bays (perfect for children), and others are great for scuba diving, kayaking, and kitesurfing. The area has restaurants for all tastes, and while there are lots of lodgings, in summer crowds flock in, so reserve as early as possible.

At-home entertainers will enjoy the expansive digs at this Upper West Side property, where a number of studios and suites feature terraces and enough space to host upwards of 30 guests. Even its more modestly sized rooms evoke big-time comfort, though, thanks to luxury bedding, signature mattresses, and an array of everyday conveniences (think Keurig machines and free morning papers). There are plenty of perks to be found beyond the rooms as well, namely at the property’s three dining venues. Serafina restaurant excels at Northern Italian plates, while LOCL offers speakeasy-inspired cocktails alongside live piano sets and a library with an original fireplace. Guests will also want to check out RedFarm, where chef Joe Ng serves clever takes on Chinese fare and dim sum, such as oxtail dumplings and BBQ duck lettuce wraps.

Nina Compton, a native of Saint Lucia in the Caribbean, came to New Orleans a few years ago to compete in the Top Chef television series. She didn’t win the culinary slugfest, but New Orleans came out ahead—a short time later she returned to set down roots by opening Compère Lapin, a charming, brick-accented restaurant in a hotel that’s a reasonable stroll from the French Quarter. It’s good to get there early to grab a drink at the bar, which treats its libations with the same seriousness as the kitchen does its food. (A frozen drink… with chartreuse.) The dishes are alive with creative Caribbean flavors—among the more memorable plates are the seafood pepper pot, black drum, and curried goat.

Though a relatively new option for tourists, the Crystal Caves of Grand Cayman’s Old Man Bay have been hosting other sorts of visitors since time immemorial: Everyone from bats (who still hang out near the entrance) to farmers (in search of the attendant guano) to pirates (where better to dodge both hurricanes and the law?). Shrouded within a healthy radius of rain forest, these stalactite-and-stalagmite-studded caverns are well worth your visit, too; whether or not you locate the treasure that some of the previous occupants are rumored to have left behind, you’ll find a wealth of natural beauty—especially the reflection of all those formations in the gin-clear rainwater lake.

Join throngs of locals on the five-minute ferry ride across Victoria Harbour between the Tsim Sha Tsui cruise pier in Kowloon, on the mainland side, and the Central Pier on Hong Kong Island (a slightly longer ride goes to Wan Chai on Hong Kong Island). This is not just any ferry: The historic green and white Star Ferries have been moving the masses back and forth for decades, with the origins of the company going back to 1880 with the service of a single steamboat, the Morning Star. Today, the classic wooden boats make the trip many times daily, and a ride provides a great view of the city’s famous skyline and a whiff of nostalgia to boot.

While Cape Point is not, in fact, the southernmost tip of Africa—as is often claimed—it is generally accepted that the Indian and Atlantic oceans meet somewhere between here and the real tip, Cape Agulhas. Still, Cape Point is about as dramatic as you can get, with the land falling steeply away on three sides, the wind whipping around the cliffs, and the ocean churning below. The road to the point, at the end of a drive from Cape Town, goes through 20 miles of nature reserve full of baboons and antelopes. For those who don’t want to walk up to the lighthouse, there is a funicular, but to reach the point itself, you’re going to have to hike.

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.

Hundreds of local and international artists have gathered each Valentine’s Day week since 2011 to make music, murals, and live installations in Honolulu’s Kakaako district. They also host block parties and panel discussions. Centered on the Lana Lane Studios collective, the event has splashed gorgeous designs all over the neighborhood... and is now expanding out to Guam, Germany, Jamaica, New Zealand, Singapore, Taiwan, the mainland U.S., and beyond. Print or save directions to the art online—http://powwowhawaii.com/mural-map—or just wander the streets, stopping for an Aussie-style coffee and botanical bounty at Paiko, then perhaps stopping by one of the world’s most famous luthiers: Kamaka Ukulele.

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.

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.

Wonderful catamarans that you can rent right off the beach.

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).