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This stylishly nautical bar and restaurant is located in the Old Town on Olivia and Elizabeth streets, nicely removed from the hustle and bustle of Duval Street. The dining room decor pays tasteful tribute to Key West’s maritime culture with sea-blue upholstered banquettes and accents like sea star mobiles, brass lanterns, compasses, and porthole windows. Perhaps it’s not surprising that the menu too looks to the sea for inspiration. A great wine list, a knowledgeable staff, and a cool sense of romance all add up to Little Pearl being a good choice for a special night in Key West.

The building that houses Moonlight Rollerway dates back to the ‘40s, when it produced airplane parts for World War II. In 1956, it was repurposed as Harry’s Roller Rink, and the current iteration maintains the original’s 2¼-inch-thick maple flooring—laid out without nails, secured by tongue and groove joints. The 1950s vibes are still alive and well, and the space has been a setting for many TV shows, movies, and music videos—you might recognize it from appearances in episodes of Glee and Modern Family. The owner, Dominic Cangelosi, started working at the roller rink in the late ‘60s before buying the place in 1985, and he still plays the organ for spinning patrons every Tuesday night.

You’ll recognize this setting as one that appears in some of the most iconic Amalfi Coast photos. The villa’s riotous beds of pansies and garden walls covered with vibrant bougainvillea are as jaw-dropping in real life. One section of the gardens dates back to the 13th century, but only traces of the medieval part remains. Most of the space is dedicated to a Romantic era–style garden that was designed by Francis Nevile Reid, a wealthy Scottish expat who owned and restored the villa in the late-19th century. In addition to touring the gardens, a small museum on the grounds with a cloister and tower is worth visiting. From June through September every year, the Ravello Festival is held here.

A clue to the appeal of the bar Tropic City is in its name: Here, sultry influences from Polynesia, Southeast Asia, the Caribbean, and Latin America fuse in a most refreshing way. The tropical theme informs everything from the decor—a tasteful mash-up of flower motifs and Portuguese tiles—to the sociable atmosphere on the outdoor terrace, which is packed nearly every night. It is most evident, though, in the carefully curated cocktail list, which dabbles in gin and mezcal while putting a heavy emphasis on rum-based drinks. Cocktails pack a punch, but light infusions such as vanilla, pineapple, and aromatic spices make it easy to put away a few—which perhaps explains why the venue has become a go-to for the city’s party set.

Santa Monica has plenty of posh spots, but the best-known might be the Bungalow, a beach-bar-style lounge right across the street from the ocean. There’s a high-ceilinged main bar inside, but the real action happens on the front patio and in the back garden, where patrons can take full advantage of the pleasant L.A. weather. Patio seating is coveted space, but if you can snag one of the funky couches and wooden tables—especially if it’s by a fire pit—you can comfortably spend the rest of the night chatting over cocktails under twinkling lanterns, a cool ocean breeze at your back. A second location in Huntington Beach has vintage interiors and ocean views right on the Pacific Coast Highway.

Walk, cycle or people-watch along the shores of Elliott Bay, a downtown stretch known for its circusy flair and spectacular vistas. You can ride the Great Wheel or visit the beloved Seattle Aquarium, home to wolf eels, sea otters, and the world’s largest octopuses. Refuel with chowder from local favorite Ivar’s Acres of Clams, then hit the market’s 200 owner-operated shops, ranging from a radical book collection to the Northwest’s oldest magic store. Just don’t turn your back on the famous salmon-slinging fishmongers: They’ve been known to wallop selfie-photographers with a plastic decoy for yucks!

Even in a city with picturesque scenes around every corner, the Petit Champlain area, located along the waterfront in the Lower Town, stands out as an especially charming corner of Old Québec. The heart of the neighborhood is the Place Royale while its spine is Rue du Petit-Champlain. While the area claims the distinction of being North America’s oldest commercial district, for most of its history its buildings housed the offices of fur traders and stevedores lodged in the tenement apartments. Today, while it’s still a bustling neighborhood, the boutiques and bistros are what draw visitors to the cobblestoned lanes. In the summer, café tables spill out into the streets; in the winter, the neighborhood exudes a Québecois sense of coziness, especially at night after a snowfall, when every restaurant offers a tempting shelter from the cold.

With only a couple of exceptions, you can’t soak in Yellowstone’s thermal features (this is for numerous reasons, not the least of which is that most are so scalding hot they’d burn the flesh off you). North of Gardiner, Montana, though, in the no-stoplight community of Pray, Chico Hot Springs has welcomed soakers to its spring-fed hot pools since 1900. Spend the night in one of the quirky rooms in the historic main lodge, originally built as a boardinghouse for miners, or in a refurbished caboose from the Northern Pacific Railroad. If at all possible, plan to be at Chico on a Sunday morning, when it serves the best brunch in Montana.

When the Art family bought the struggling Chico Hot Springs Resort in 1972, some of the earliest improvements they made were to its dining room. The idea was to create one of the best restaurants in the state; if guests came for the food, maybe they’d spend the night. The family succeeded. Today the Chico Dining Room is so beloved it spawned a cookbook, A Montana Table: Recipes from Chico Hot Springs Resort. While ingredients are as fresh as can be—with produce from on-site greenhouses, meat from local ranchers, seafood flown in overnight from the coast—the menu includes some dishes that have been around for more than 40 years. The classic Chico meal is beef Wellington (service for two) and, for dessert, a Flaming Orange, which is exactly what it sounds like.

Is this polished industrial space, in an odd corner of the Centro, the thinking man’s disco? Organizers prefer to speak in terms of a cultural center, and the installation’s multiple spaces are venues for everything from literary events and screenings to a dynamic agenda of live-music performances. But it’s the DJs and dancing that are bringing in crowds, crowds that are alternative and low-key, creative, sex-pref-neutral, and seemingly little impressed that their hangout has become so fabulous. Priced-to-move libations and overall edginess keep the crowd skewing young; the space’s various environments add variety to your night out—and sometimes there’s even a place where you can chat (or canoodle) without screaming.

Ponce is Puerto Rico’s second-largest city and is nicknamed the “Pearl of the South.” Life here seems to move at a slower pace than San Juan, and that’s the way locals like it. For them, there’s nothing better than an evening or weekend stroll around Plaza Las Delicias, the main square, which is full of history and entertainment. Stop by the unmissable red-and-black–wooden firehouse (now a museum) to learn more about the central roles that fire and firefighting have played in Ponce’s history. Then work your way around the square to see Ponce’s symbol, the lion, anchoring each side of the plaza, the church, the fountains, and finally, Kings Cream, a no-frills emporium that sells small cups of ice cream—with flavors such as passion fruit, peanut, guava, and coconut—at bargain prices.

The beloved Dar Ahlam resort has taken its show on the road with Route du Sud, a six-night driving tour to five destinations with three private retreats that showcase the shape-shifting landscapes of isolated southern Morocco, one property at a time. The first stop is the hillside Maison des Arganiers, two and a half hours from Marrakech, in a rocky landscape facing miles of argan groves; next comes La Maison de l’Oasis, nestled in an oasis of palms; and the final private destination is the dramatic La Maison Rouge, which sits at the edge of a red canyon. Along the way you have beach picnics, nomadic campouts, and scenic drives through dramatic desert dunes.

A few years ago, Bósforo was a nondescript bar in the capital’s Centro Histórico (Historic Center) neighborhood. Its decor was nothing to write home about; in fact, it was so dark it was hard to make out whether there was any decor to speak of. Fast forward to today, and the dark, dull interior hasn’t changed. Nor has the bar’s focus: mezcal. The smokier cousin of tequila is an agave-based spirit that has grown exponentially in popularity over the past several years. Most of the bar’s offerings are small-batch mezcals in bottles with handwritten labels. What you try today may not be available at all the next time you visit. What has changed in the past year or two is Bósforo’s visibility. Once a bar that was really only for locals in the know, Bósforo is now visited by mezcal lovers from all over the world. If you’re a fan of the spirit—or you haven’t yet tried it and would like to—Bósforo is worth a night out in the Centro.

Southwest of Anguilla is one of the island’s top three beach areas: the two-mile-long brilliantly white stretch at Rendezvous Bay. Its long shore, steady breeze, and calm Caribbean waters provide a break from the crowds at Shoal Bay and Sandy Ground. The western end does offer some fun daytime beach-bar action, which grows rowdier at night and on the weekends, when the famous Bankie Banx’s Dune Preserve venue attracts residents and visitors for live music. You can view St. Martin, across the channel, from shore.

I love visiting big iconic bridges during the sunset. Trips at dusk to the Golden Gate Bridge and the Brooklyn Bridge have resulted in spectacular photographs of the urban landscape. The Sydney Harbour Bridge was another great experience! The bridge is accessible by foot or by bike and is surrounded by some of the biggest attractions in Sydney. More adventurous types might opt for the Bridge Climb Tour (http://www.bridgeclimb.com/) where participants get to scale the summit of the 134-meter arch for panoramic views of the city. And yes, they offer a Twilight Tour near sunset (and a dawn tour at sunrise). We were content walking across the bridge on the pedestrian walkway. It was a brisk spring evening in Sydney, and we didn’t envy the tourists climbing the bridge overhead. The views from the bridge are stunning in every direction, and it is a magnificent vantage point to see the Sydney Opera House and the Central Business District.

Though the beaches of southern Kerala may get more attention, the Malabar coast shores of the northern part of the state are no less beautiful—and offer plenty of their own attractions. Case in point: Bekal Beach, a wide, sandy stretch along the Arabian Sea, set under historic Bekal Fort. The cove-shaped beach offers plenty of room to stretch out and soak up the sun, shallow waters for swimming, and artistic touches like a rock garden, murals, and public sculptures. If you don’t want to get sand in your shoes, take a stroll along the boardwalk, or venture up to explore the Fort complex. Little ones will like the beach’s children’s park, while adults should come back at night, when the beach is illuminated, to enjoy the magical atmosphere. Further along the shores, you’ll spy fisherman bringing in a daily catch that might include mackerel, reef cod, and tuna.