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Located in a former shoe factory, City Museum devotes 600,000 square feet and four levels to play for all ages. The museum was the brainchild of artist and entrepreneur Bob Cassilly—along with a crew of 20 artisans known as the Cassilly Crew—who constructed the space from objects found around the city, from construction cranes and fire trucks to church pipe organs, old airplanes, and plenty of reclaimed building materials. The result is a wonderfully weird and wacky museum that’s constantly evolving, depending on what’s been donated and collected recently. There’s a sky-high jungle gym, a rooftop Ferris wheel, an aquarium, and multi-story slides that once served as chutes for shoes. The museum has a “no map” policy to encourage exploration, but does advise visitors to bring their own flashlight—you never know what you’ll find in those dark caves.

There’s a carefree summer camp spirit at Ruschmeyer’s, a boutique retreat in Montauk where a central garden full of hammocks and picnic tables creates a relaxing backdrop. First built in 1952 in a shaded stretch of lakeside woodlands in Montauk, the hotel now features recently renovated rooms inspired by camp cabins with cedar-plank walls, a hammock, and some with an outdoor charcoal grill. Ruschmeyer’s has an appetite for culture, seen in a rotating series of music performances, guest DJs, and artists-in-residence. This is a place to play, and the hotel happily arranges paddle boarding, fishing, and yoga. Start your stay on the central lawn, called the Magic Garden, with a game of ping-pong before drinking and dancing the night away at the hotel’s bar, the Electric Eel.

Each evening as the sun sets, Stone Town’s Forodhani Gardens park transforms into an open-air food market. Skip the fish kebabs and head straight to the vendors selling urojo, a thick mango-and-tamarind soup served alongside chickpea fritters, boiled potatoes, cassava flakes, chutney, and as much hot sauce as you dare. Follow it up with hand-pressed sugarcane juice with ginger and lime.

The wild and rugged coastline of Sumba, Indonesia has yet to be discovered by most travelers to Indonesia due to the allure of other popular islands, namely Bali, Java and Lombok. Sumba has yet to be developed and there are only a handful of accommodations spread around this large island catering primarily to surfers seeking the fabled monster waves that break on its reefs. The beaches are long stretches of soft white sand and you will most likely have them to yourself. The villages on the island are very primitive and constructed of timber and tall thatch roofs. Sumba is serviced by air a couple times and week at tiny airstrips in either Waingapu or Waitabula. Cancelations are frequent and I ended up stuck on the island a few days longer than I had anticipated. Sumba feels like you stepped back in time a couple hundred years and it’s a real adventure.

Get down and dirty on an unforgettable spelunking experience at the Venado Caves, 45 minutes from La Fortuna. The caves were formed some 15 to 20 million years ago by tectonic shifting and erosion from underground streams. In them, you’ll see stalagmites and stalactites galore, and get the chance to check out colorful frogs and fascinating marine fossils and learn about the bat communities hanging right over your head. The experience is real (and really humid)—so wise adventurers bring insect repellent, knee pads, and an extra change of clothes. Waterproof your camera, too.

Beachy espadrilles, cloth bags printed with cheeky Italian phrases, and colorful Cruciani bracelets are just some of the fun inventory found in this small, stylish shop. There’s a little bit of everything here: bikinis and summery dresses, art books, and local crafts like an arty ceramic interpretation of il ciucciariello, the little donkey that is the local symbol for good luck. The shop also stocks useful maps of the many paths and beaches along the Amalfi Coast.

Head to a place that succeeds in squeezing many centuries’ worth of artifacts from multiple civilizations into a manageable—and beautiful—17th-century mansion: the Museo de Arqueología UNT (National University of Trujillo Museum of Archaeology, Anthropology and History), housed in La Casa Risco. You’ll find remnants of the Chimu, Mochica and Incan empires in the form of jewelry, clothing and ceramics, as well as displays that explain the rise and fall of these civilizations.

Of all the Greek islands, sybaritic Mykonos has the most to offer big spenders. Instead of worry beads and flip-flops, the shopping scene is more Louis Vuitton and Lalaounis jewelry. Ergon, a stark white concept store with rag rugs installed between the rafters, stocks an exciting collection of clothing and accessories by Greek designers. Embroidered caftans, tasseled espadrilles, and colorful straw fedoras are just the thing for sashaying through town or showing off your tan at beach bars such as Alemàgou and Scorpios. Gifts inspired by ancient Greece include a Trojan horse paperweight, a minimalist amphora pendant, and gold olive-branch earrings. You can also customize your own espadrilles, T-shirt, or beach tote.

Amsterdam’s State Museum reopened in 2013 after a decade of renovations, and it is oh so worth a visit! Weave your way through the museum’s vast assemblage of historic art (there are over 8,000 pieces!) to check out works from Dutch masters such as Rembrandt, Van Dyck, and Vermeer in person. The collection’s best-known and most prominently displayed piece is Rembrandt’s Night Watch, but visitors can find everything from sculptures to artifacts from both the Netherlands and Dutch-colonial territories around the world. Opt for the multimedia tour for a special surprise.

Reservations required—and no wonder. The tours at the Neon Museum sell out months in advance. A walk through the museum’s famous “Boneyard” (where neon goes to die) is fascinating, from motel row to the first integrated casino (one that shut almost as soon as it opened), and the Stardust, with its nuclear testing-inspired font. All of this comes alive thanks to the museum’s famous docents, all art history buffs with loads of family history or other personal anecdotes.

Imagine dining right on the beach, toes in the water, under swaying palm trees along a perfect little crescent bay in Savaneta, Aruba’s charming fisherman’s town. Add a fine selection of delicious fresh seafood, an extensive wine list, and exceptional service for a romantic evening that exceeds all expectations. Go early to catch the sunset.

A sliver of a boutique, with several levels, and discreetly tucked into a quiet street in the Juarez neighborhood, Loose Blues artfully serves up a clever selection of accessories and apparel for its deliberately insouciant, hipster clientele. Its curatorial strategy starts with staples like vinyl LPs and midcentury barware, then drills down to men’s and women’s clothes and footwear that walks a line between Bettie Page, lumberjack, and future shock. Once you’ve loaded up on Hawaiian shirts and skinny-girl jumpsuits, as well as tattoo-inspired and other Mexi-kitsch artworks, retreat to the upstairs café and restaurant, whose airy industrial vibe complements a menu of delights like herbal teas, artisanal brews, and light Japanese fare.

On the corner of a rather scrofulous downtown block and across the street from the Ace Hotel’s event space, Wildfang is a self-described “home for badass women.” Whether it’s street style with a feminist message—even in Portland, it’s not every day that one finds a “Slay the Patriarchy” baseball cap—or high-fashion clothing that works on all sorts of body types, Wildfang packs it all in. For hangers-on who aren’t as interested in shopping or fashion, the bar inside the store provides liquid relief, including beers designed in collaboration with 10 Barrel that were created by women brewmasters.

Enjoy all the thrills of skydiving with none of the drama—no parachute or airplane at all. After a brief orientation, participants pull special flight suits over their clothes and then enter a wind tunnel, where all the excitement takes place. A giant fan that creates wind speeds of up to 120 miles per hour lifts the skydiver and holds him or her aloft for an exhilarating three minutes. Having doubts? Skilled coaches are on hand and the experience is far safer than jumping out of a plane. It’s also a great first step for those who’ve hesitated to try skydiving.

The mother of unique Bangkok retail experiences is undoubtedly Chatuchak Weekend Market, Thailand’s largest outdoor bazaar. Known as Jatujak or simply JJ, it has 15,000 stalls spread over 35 acres and sells almost everything under the sun. This is the place to buy a Beatles cushion or shop for a new pet cobra or a hand-carved Buddha icon. With 200,000 people descending on the market every weekend, it’s best to come early, and perseverance can uncover a veritable treasure trove of collectibles ranging from beautiful ceramics and handicrafts to exquisite jewelry.