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Charlie’s is old-school New Orleans writ large. It’s one of a handful of surviving notable neighborhood steak houses (it’s not far from where the original Ruth’s Chris was also once a neighborhood spot), a no-frills joint with faux-wood paneling on the walls and no menus to hand out. The waiters ask you what size you want, and also if you’d like to start with an order of fried onions. (The correct answer is yes.) Pro tip: Kick off your evening an hour earlier and a couple blocks away at Pascal’s Manale with a dozen or two bivalves at the marble oyster bar of a revered Italian-Creole “red gravy” spot.

There’s no better place in Hobart for a sundowner than this bar and restaurant, situated on the pier where the ferry to the Museum of Old and New Art departs. Its menu is filled with Asian-inflected dishes such as Korean fried chicken and pork belly bao.

This spacious North Shore eatery and watering hole riffs on the beloved Honolulu original. It makes a strong showing in the “pupu” (appetizer) department with nibbles like poke, pot stickers, kālua-pig fried rice, Korean-style chicken wings, and nut wraps in buttercup lettuce. Cool down with a light, refreshing cocktail unique to this location, such as the Hokulani (citrus, Three Olives vodka, and elderflower liqueur, splashed with soda) or the Hawaii Five-Bo (strawberry daiquiri with Bacardi rum, habañero syrup, and piña colada foam). As with many O‘ahu eateries, the prices can seem a bit more Manhattan-stiletto than “flip-flop surfer bar.” But the flavors and charming service tend to carry the day! (Note: it’s a short stroll to the public restrooms, involving some unlit steps at night. Plan ahead.)

Hop on the free ferry from the city’s Central Station for the 15-minute ride to the NDSM wharf, an old shipyard that’s transformed into a hipster haven with restaurants, bars, and artists’ studios. The waterfront “beach bar” Pllek is a popular spot here; built out of old shipping containers, the soaring, dual-level space has an industrial vibe, with corrugated-metal walls warmed by bright artwork, an indoor fireplace, and huge windows looking out over the IJ River. But it’s the man-made beach that draws crowds in warm weather, with comfy beanbags and loungers where you can while away the afternoon. There’s a nice selection of beer and wine; the food is simple but surprisingly good, and it’s crafted with fresh, organic ingredients. Pllek also hosts live-music events, DJs, dance parties, films, and morning yoga classes.

The Hole is a geologic formation that offers a dramatic look at the same karst process that created Conch Bar Caves and other limestone sinkholes and caverns found throughout the Turks and Caicos Islands. As its name implies, the Hole is area’s largest limestone sinkhole, about 60 feet deep and 50 feet across. A pool of water at the bottom connects to Juba Sound’s nearby ponds through an underground tunnel. You can rent a car and drive to the Hole on the east side of Juba Sound; however, use caution when walking near the edge, as limestone can crumble.

St. Kitts’ water taxis—basically anyone with a boat willing to make the crossing to Nevis—will drop you right on this beautiful stretch of sand, making Oualie Beach the perfect day trip. Once on land, head to the Oualie Beach Resort, where you can hang with guests and locals at the on-site restaurant and bar. If you’re feeling adventurous, ask the bartender for a sample of one of the house-infused rums, made with a variety of local plants and herbs. Afterward, walk down to the beach, where you’ll find watersport vendors and even a small spa for some additional relaxation.

One of the most popular anchorages in the BVI, Cane Garden Bay is home to a lively boating community. It makes a great day trip, whether you arrive by land or by sea. In this scenic cove, calm blue water laps a gentle arc of blinding white sand. Open-air beach bars offer lounge chairs and rum drinks; a few shops sell souvenirs, along with provisions for the sailors coming in off their boats to stock up.

Parque de los Novios, in the center of Santa Marta’s colonial sector, is perfect for people-watching in the late afternoons when the tropical heat abates. Everyone from the gentry to the common folk—not to mention a plethora of brides posing beneath the gazebo—seems to treat themselves to a nice stroll around the park. Nearby restaurants and bars come alive after night falls, as do, of course, street artists and musicians.

Bloody Mary’s, entertaining tourists since it opened in 1979, is one of those Bora Bora experiences that simply must be done. The ambience is beach-bar hip, with sand floors, colored lights, and coconut stools in a dining room under a thatched roof and surrounded by tropical foliage. Even if you don’t eat here, at least come for a cocktail to experience the vibe and mingle with the crowd of local pension, or guesthouse, owners, visiting celebrities, and other travelers. The food’s quite good, too: Fresh fish, seafood, and meats are grilled, American-barbecue style, with tasty results.

The supper club is reinvented for the next generation at Yvonne’s, banishing any possible ghosts from the former Locke-Ober’s, and leaving just enough of the old girl (the beautiful hand-carved original bar and woodwork) to recognize her former self. The entrance is a bit mysterious, and the outer-bar area a happening scene. Walk through the “library,” a cozy space that looks like it’s right out of an Anthropologie catalog, and you’ll find lime-green banquettes, fancy chandeliers, and a modern web of lighting. The small plates are meant for sharing and make it possible to taste a good many flavors from the kitchen. Baked oysters Savannah are a nod to the well-heeled crowd, combining lobster, porcini cream, and Parmesan into a decadently rich mouthful. Seared halloumi has just the right sweet-and-savory combination and is a favorite that doesn’t disappoint. Be sure to make a reservation; there is usually a line. Try one of their crowd-pleasing punch bowls presented in unusual vessels. The “Goodbye, Me"—with Moroccan-mint-infused gin, sake, watermelon, lemon, and champagne—lives up to its name.

Consistently ranked among the world’s top beaches, and easily among the most popular and visited ones in Anguilla, the white and light pink sands of Shoal Bay host a casual and social atmosphere, with a plethora of bars and eats. The bright turquoise water is what Anguillan dreams are made of; water-sports options abound, from snorkeling right off the beach to parasailing and diving. Weekends get busy, with families flocking here and music echoing along the strand, especially from Gwen’s Reggae Grill. But if you just want to rent a chair and relax for the day, you can normally find a spot of Shoal Bay to call your own.

These days, a hip design hotel isn’t worth its salt unless it’s also home to an almost painfully trendy bar. But when Story Hotel first opened in 2009, on the border of two of Stockholm’s coolest neighborhoods, it set the standard to which all of the city’s subsequent boutique hotels would be held. The Story formula is deceptively simple: take one historic building in an achingly cool European capital and strip it down to exposed brick and concrete, and original hardwood floors, before decorating it with a sleek, unpretentious style that epitomizes Scandinavian design. Add a sprinkling of colorful graffiti art, and pair faded Persian rugs with collaged photographs and leather chairs. Make sure some rooms are small and affordable, while others are spacious and decadent.

The cuisine needn’t be fancy, but it ought to be high quality, just as the cocktails must be inventive and delicious. And don’t let the DJ-accompanied scene turn pretentious; everyone should feel welcome, and among friends. Story’s formula works, and there’s a reason this original boutique hotel is still one of Stockholm’s best.

After a period of tribal skirmishes, the Fijians suddenly looked up and found they’d been colonized by the British. The Grand Pacific Hotel, built in 1914, shows just what fun it was to be British back then. Built along the same design as a ship—with promenades and prominent views—the Grand Pacific provides an interesting contrast to Waikiki’s old hotels, which all face inland. You can’t tour the Grand Pacific, but it’s worth a walk by or a drink at the bar.

A little beyond the city walls, and just a few blocks from the Musée National des Beaux-Arts de Québec and the Plains of Abraham, Avenue Cartier offers a different shopping experience than what you’ll find in Old Town. This is a part of the city more popular with locals than tourists, and instead of shops selling sweatshirts with moose and maple-leaf designs, you’ll find upscale stores and boutiques. The street is also known for its dining and nightlife options, offering a wide selection of restaurants, pubs, and bars where you can take a break from the hard work of shopping.

Hoshinoya Tokyo is a modern ryokan that gracefully stands between the Imperial Palace and the Journalism Center of Tokyo. Built upon the heritage of Japanese inns, this hotel exudes warmth and minimal elegance from every angle.

At first glance, I was drawn to the understated steel pattern of the facade that’s graphically new, yet mysterious ancient. Once inside, I was immediately soothed by the interior decor and furnishings crafted from the finest woods and fibers native to Japan. On each floor, there is an Ochanoma lounge where you can read or enjoy tea by the diffused light of the shoji screens. My favorite part of the ryokan is the hot springs on the top floor. If you have seen and love the Skyspace series from artist James Turrell, onsen is where you can truly feel connected to earth, water and sky.

I travel for the opportunity to learn and to see things anew. On the subject of Japanese aesthetics, the novelist Jun’ichiro Tanizaki writes “We do not dislike everything that shines, but we do prefer a pensive luster to a shallow brilliance, a murky light that, whether in a stone or an artifact, bespeaks a sheen of antiquity.” I read this as a young design student but it’s only until my stay at the hotel that I vividly saw this sheen of antiquity. I highly recommend Hoshinoya Tokyo for the finest amenities and a chance to experience the modern Japanese approach to beauty and design.