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In a city that takes itself so seriously—running the United States is an intense business, after all—the Hotel Madera is a breath of fresh air. Just a couple of leafy blocks from always-lively Dupont Circle, the Kimpton-run boutique hotel looks like a 1960s apartment building on the outside, belying interiors adorned in colorful, batik-inspired fabrics and perks like in-room yoga mats and an evening wine hour. In other words, the Madera is the kind of place where you relax. The laid-back and trendy restaurant takes its design cues from a fairy-tale forest, and pets are as catered to as children and bachelorette groups. It’s hard to beat the Dupont Circle location, too, which puts the White House, the Kennedy Center, and trendy neighborhoods like Logan Circle and U Street all within throwing distance. No, it’s not the fanciest stay in town, but D.C. doesn’t need another fussy hotel to attract visiting dignitaries—and you’ll have more fun at the Madera, anyway.

Also known as the 36 Streets (though it’s made up of more than 36 streets), this neighborhood is a warren of alleys and lanes that was, according to some legends, home to 36 artisans’ guilds; streets here were named after the artisan items that were once sold on them (Hang Bo was the location for bamboo products; Hang Ma was where paper objects were sold). Each road today still specializes in a particular category, with some still related to the traditional item. Streets especially popular with tourists shopping for souvenirs, as well as those in search of photo opportunities, are Hang Bac (silver goods, now also filled with gift shops), Hang Ma (religious paper wares, then and now), and Hang Dau (oil products, though currently a center for shoe vendors). Among these timeworn businesses, visitors will also encounter outlet stores selling Gap, Banana Republic, and North Face clothing—some authentic and some fake. The quarter is also packed with hotels, hostels, restaurants, and bars, making it a busy destination at all hours.

Mile-long Newbury Street, lined with handsome 19th-century brownstone homes, is synonymous with shopping in Boston; it’s also the place to go to get your hair done up nice. Between Arlington Street and Massachusetts Avenue you’ll find an eclectic mix of boutique and designer shops, hair salons, art galleries, and restaurants that generally skews upscale (Tiffany’s, Chanel, Dolce & Gabbana) but also includes the original location of the Newbury Comics record store and a T.J. Maxx. Eminently strollable and dotted with sidewalk cafés, Newbury Street is the hip heart of the Back Bay neighborhood, perfectly distilled at eye-candy drinks-and-dining hot spots like Sonsie and Stephanie’s on Newbury.

From its beachfront locale to the sweeping terraces and sliding-glass doors, everything about this hotel is aimed at maximizing views of Bali’s most sought-after shoreline. Local stone and wood put an Indonesian twist on the resort’s Thai design, which incorporates a dark-wood color scheme, a mini waterfall, and lattice screens. The hotel offers one-of-a-kind experiences, including special-occasion dinners on the beach and spice-infused cooking tours that introduce guests to regional flavors (don’t miss Spice Spoons, in which you’ll sample exotic fruit and other local ingredients, or the seaside Indonesian cooking class with a master chef). Bustling Seminyak lures travelers to its restaurants, bars, and nightclubs—often early into the morning—but Anantara’s spacious sundecks, refreshing pools, traditional spa suites, and umbrella-shaded beach chairs are waiting to revive you the next day.

It took no time for this neighborhood restaurant from chef and owner Diana Dávila to garner major fandom. The menu—a compilation of antojos, or Mexican small plates—is a nod to Dávila’s Mexican heritage and an invitation to diners to experience the country as she did growing up. Expect that journey to unfold with the likes of fish with yellow mole, enchiladas potosinas, and an array of taco options (from beer-can chicken to butternut squash). Drinks are just as groundbreaking—opt for the Chicana, a floral and herbaceous coming together of hibiscus, mezcal, gin, Chartreuse, and maraschino.

For an especially scenic drink, try the umbrella-shaded Beachside Bistro at the Summer House. Down a flight of stairs into the gentle dunes, you can’t get much further east unless you want to go swimming. A full bar is available and you can snack on the likes of lobster salad or crab cake. Come at sunset, and even though you won’t see the sun itself, the entire sky glows pink and dreamy as the waves roll in.

Head to Willemstad’s Pietermaai district at happy hour, and you’ll quickly stumble across a row of festive Euro-style bars on Nieuwestraat—but none are as funky and eclectic as the Cuban-themed Mundo Bizarro. This indoor-outdoor lounge-restaurant is filled with antique furniture, bold paintings on colorful walls—look for the older Cuban woman wielding a cigar and a sassy stare—and knickknacks from around the planet. Try some of the most beloved items from its international menu, such as smoked-beef carpaccio, rib eye, salads, and quiches. Fridays at 10 p.m. are popular for the live salsa band.

This airy poolside restaurant serves up Curaçao classics like iguana soup, goat stew, and fried funchi, a crispy (and addictive) polenta. But the menu has something for even the pickiest of travelers. In the mood for a regular ol’ burger? Rancho El Sobrino offers one of the best on the island. Can’t get enough fajitas, like Michael from The Office? You’ve got four varieties to choose from here, including a veggie option. After your meal, stroll through the adjacent garden or order your favorite cocktail from the veranda bar—and gaze up: You’ll see a bed frame hanging from the wooden ceiling. Because why not?

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.

While not as large as other ancient Mayan cities in the region, Tulum draws in visitors for its stunning setting of centuries-old temples perched on a cliff by the Caribbean Sea. You’ll pass a large market with souvenirs, a casual Mexican restaurant, and even a Starbucks before reaching the entrance, where a train can take you to the site if you’re not up for the 10-minute walk. It’s advisable to hire a guide to fully understand each structure’s significance and the history behind the ruins; informative signage is all but nonexistent. Don’t forget to bring your swimsuit, as the site encompasses a white-sand beach with soothing waves and beautiful rock formations that’s reached by a long wooden staircase.

When temperatures soar, the best thing you can do for yourself, and anyone you are with, is to buy a pass to one of the hotel pools. The Riad Alkantara is situated at the heart of the medina and offers a long, deep, aquamarine-colored pool surrounded by a small but lush garden busy with butterflies and warbling songbirds. It’s usually very tranquil, but it’s worth arriving around 11 a.m. to be sure of a sun bed in high summer. Note also that service is painfully slow, so if you want to order a simple lunch (sandwiches, salads) be sure to order at least an hour and a half before you actually want to eat.

In the Ville Nouvelle, the Marriott is another good option and a better bet if you have kids in tow, as it has a shallow pool for children as well as a large pool for adults. Plentiful sun beds, not to mention a decent Italian restaurant that serves cold beers and chilled Moroccan wines as well as child-friendly pizza and pasta, add to the perfection. The Hôtel Les Mérinides is situated high on a ridge above the medina and it has a medium-size pool surrounded by a dining terrace with expansive views. It’s more exposed than the other two, but rounding off the day up here with a gin and tonic as the sun goes down over the ancient city is arguably one of the most magical summertime experiences you can have.

Finally, if time and budget allow, it’s worth booking transport to ferry you out to Dar El Mandar, less than an hour’s drive away from the city center, near the Middle Atlas town of Imouzzer (pass price includes lunch). Perched on a hillside overlooking the Saiss Plains, you can spend a delightful day lolling poolside amid terraced gardens dotted with cushion-strewn Berber tents for those all-important afternoon siestas.

First, Brooklyn’s Coney Island is not, in fact, an island, having been attached to the rest of the borough by landfill since the 1920s. What the area is best known for, however, is its heyday from around the 1880s through World War II when it began as a posh seaside resort area and gradually became a beloved beach destination, thanks to a number of amusement parks. The appeals of Coney Island declined after the war (historians attribute this to the proliferation of both air-conditioning, which made escaping to the shore less important, and the automobile, which made it easier to reach nicer sandy stretches on Long Island). In recent decades it has increased in popularity again. Brooklyn residents, and visitors to New York, have embraced anew the retro charms of the boardwalk and the rides that are still operating, like the Cyclone roller coaster and the Wonder Wheel Ferris wheel. The towering Parachute Jump has been abandoned, but it still stands as an impossible-to-miss landmark. Brighton Beach sits next to Coney Island and is a largely Russian neighborhood where restaurants are happy to serve any diners who appreciate copious amounts of vodka and Russian specialties.

Aspen is known for its glitz and glamour, but that doesn’t mean you have to be a millionaire to vacation here. If your first priority is to be outside, then Hotel Aspen is an ideal and affordable base, located downtown at Main Street and Garmisch. The hotel boasts that it offers four-star amenities at three-star pricing. You won’t find a sceney restaurant and plush spa, but the hotel compensates with thoughtful staff and tons of complimentary services. While many hotels charge hidden extras, Hotel Aspen prides itself on free guest parking, free Wi-Fi, free breakfast, and even a free après-ski reception with wine and cheese. Even the most basic rooms—Deluxe Rooms—feel roomy and come with a refrigerator and coffeemaker. Families will like the spaciousness of Junior Suites, while anyone looking for a home away from home will want to book the one-bedroom apartment, which has a living room and fully stocked kitchen. Pets are also welcome, for a $20 daily fee.

Australian-Vietnamese celebrity chef Luke Nguyen has put his energy into creating fresh, modern, healthy renditions of Vietnamese street food and traditional family recipes at Moi Moi, his new Hong Kong restaurant. A master at balancing sweet and sour tastes as well as spicy and bitter, Nguyen gets big raves for his food, especially the panfried rice cakes topped with tiger prawns and caramelized pork neck. Other hits include green tea–smoked duck in rice-paper rolls, citrus wild salmon, caramelized Kurobuta pork belly, a pho made with raw Wagyu beef, and slow-braised free-range chicken drumsticks with coconut juice, fish sauce, ginger, and garlic. Moi Moi has an extensive and creative cocktail menu to accompany the feast.

New Orleans may be home to America’s most festive thoroughfare, Bourbon Street, but Key West’s Duval Street is a close second. This two-kilometer-long (1.25-mile-long) road runs from north to south, from one end of the island to the other, and passes through the city’s historic Old Town. It’s lined with bars, restaurants, stores and galleries—many of which are among Key West’s most famous, including Sloppy Joe’s, a Hemingway hangout back in the 1930s and still a hotspot today. By day it’s mostly for shoppers, but it really heats up at night, with huge crowds strolling up and down the street, live music spilling out from the bars and a party atmosphere all around.