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From the dusty street, the Hotel El Convento in León, Nicaragua, beckons with its stately façade and red Spanish-tiled roof. Step inside and you instantly feel at home amidst ornate period furnishings that are surely a far cry from the building’s humble beginnings as the 1639 San Francisco Convent. The elegant Restaurante El Victoriano offers an indoor-outdoor retreat centered on the hotel’s manicured, tropical courtyard—an example of the colonial hacienda style found throughout León. The restaurant is a meeting place for people from all walks of life—aged former Sandinistas who now hold positions of leadership, locals splurging on a fine meal, or foreign students from one of the city’s many Spanish language schools seeking tranquility and an excellent cup of coffee.

With headquarters in Portland, Oregon, the Ace Hotel brings a dose of Pacific Northwest cool to the Flatiron District of Manhattan. Located in a turn-of-the-century building, the Ace has become a hub for stylish visitors and freelancing New Yorkers—locals often set up shop in the hip lobby to work and sip Stumptown coffee. The aesthetic is laid-back yet creative, with fun local art, free Wi-Fi, and quirky touches like tabletops made from discarded Hubble telescope lenses. The Ace is unpretentious and inviting, with a social and interactive lobby and two destination restaurants. Rooms range from small bunk rooms to spacious loft suites—offering a match for a variety of price points.

While San Francisco’s Contemporary Jewish Museum dates back to 1994, it moved into its current location in 2008. The heart of the museum’s new home is a 1907 Pacific Gas & Electric power substation, with additions designed by one of architecture’s leading figures, Daniel Libeskind. The museum tends to take a thematic and often surprising approach to its subject with, for example, exhibitions of artists inspired by the biblical book of Genesis and others focused on the notable personalities of the Jewish life of California, America and beyond. If you are looking for some unexpected gifts, the museum’s store carries updated menorahs, humorous T-shirts and a large selection of books on Jewish culture and history.

The vibe in Waikiki is the most frenetic of all the spots in the islands, but there is an escape. The scene at the current iteration of the classic Hawaiian hangout, Duke’s, is a step back even by Oahu standards. Best approached via the beach to enhance the original feel and avoid the mall-like carnival from the street entrance, this is the kind of bar that welcomes sand on your flips. Slip in for happy hour and be prepared to jockey for a spot. Even with the crowd, the music, the food, the drinks are all designed draw you back to a simpler time when Duke was still riding the longboard. I’m partial to the beers and french fries, but will never refuse a fish taco. With a long relationship with the Kona Brewing brand, I opt for the Longboard larger or Fire Rock Pale ale. The umbrella drinks don’t disappoint, but neither do the gin and tonics. The local musical talent that ply the stage at Duke’s are traditional Hawaiian in style and like to keep the island theme front and center. There is a family vibe to the musical community, much like the rest of Hawaiian culture, and it’s not unusual to get a sibling or cousin to come up on stage and do some traditional Hawaiian dance or help out on a song or two. There was an 8 year old girl that got asked to come up on one of our visits and she blew the crowd away! The strip a Waikiki can be a bit daunting in terms of relaxation, but Duke’s remains my refuge from the madness. Aloha.

For those who aspire to travel as trendsetters in Jamaica, it helps to know that Port Antonio, way out on the eastern end of the island, is the destination to head for. And the address to shelter at is the Trident Hotel, whose 13 waterfront villas would not look out of place on South Beach. Nor would the crowd that hangs around its infinity pool or in its restaurant, Mike’s Supper Club, where local musicians and the occasional celeb sit down to knock out tunes on the 1917 Ferrari-red grand piano. The Trident Castle, a kind of fantasy annex, is a former private residence whose grand rooms, sea-view terraces, and dollhouse-size chapel make it ideal for destination weddings. A hard road to get there? Not for guests who avail themselves of the helicopter pad.

The centerpiece of a vast resort, golf club, and residential community complex, Rosewood Bermuda sits on 240 acres of waterfront land overlooking Castle Harbour, Harrington Sound, and the Atlantic Ocean. The recently refurbished resort is anchored by the Manor House, where 88 guest rooms blend classic cottage-style architecture and modern interiors that continue to set the standard for today’s luxury seekers: think canopy and four-poster beds, plantation shutters, and colonial-era antiques, all set against a cool white backdrop. Spring for a deluxe poolside room, which also has access to a private poolside daybed. Just don’t expect too much down time. Three on-site restaurants and two bars are beyond selfie-worthy, treatments at the spa incorporate local ingredients like cedar and juniper, and hotel guests receive membership to the 18-hole Roger Rulewich–designed golf course, tennis courts, and a beach club that sits on an exclusive stretch of pink sand for the duration of their stay.

Despite its size (10 square miles) and population (fewer than 170 permanent residents), Little Cayman enjoys a worldwide reputation among serious divers. The island is renowned for its exceptional underwater visibility and vertigo-inducing walls, especially north-shore Bloody Bay. Dive boats flock to Three Fathom Wall, where bulbous coral heads teeming with fish rise to within 10 feet of the surface. Snorkelers are likely to encounter schools of blue tang and stoplight parrot fish, as well as hawksbill turtles and nurse sharks.

Set on a picturesque terrace high above crashing waves, BijBlauw has breathtaking views and an effortlessly romantic vibe. The kitchen is partially open, so you can watch the chefs prepare fresh ingredients while you bask in the breeze. Try the truffle risotto, braised oyster blade steak, or “funky funchi,” a savory cornmeal mash with Parmesan cheese and a delicate poached egg. Want to make it extra special? Reserve a seat at the Chef’s Table, where you and your friends will get to sample the ever-evolving tasting menu, with wine pairings included. BijBlauw is a solid choice for breakfast, too—if you’re up early enough, grab a croissant and head for one of the coveted spots next to the water. Vegetarian options are available.

This archipelago off the coast of La Paz (which takes the name of the main island) is a protected UNESCO Biosphere Reserve. While the islands are uninhabited by humans save for a small fishing camp made of temporary structures, they’re home to a great variety of flora and fauna. In addition to dolphins, frigate birds, and ring-tailed cats, you’ll find the only known black jackrabbit population in the world. Celebrated eco-friendly activities company Cabo Expeditions leads daylong archipelago tours that include exploring the mesmerizing volcanic landscape, a ceviche lunch, and an opportunity to swim on Ensenada Grande Beach—often cited as one of the world’s most beautiful—plus guided snorkeling with the incredibly playful pups at the Los Islotes sea lion colony.

My ideal habitat is a warm day on a tropical beach. I’m also a sucker for beauty in all its most unusual forms (part of the reason I’m on the Board of Burning Man). So, when I heard about the Harbin International Ice & Snow Festival in northeast China (Manchuria meets Siberia: that just sounds frozen!), my initial reaction was, “How far would I travel and how cold would I get all in the name of experiencing an aesthetic phenomenon?” So, after 90 degree humidity in Malaysia, two planes delivered me to this cursed, desolate part of China (20 degrees below zero). Amidst the Siberian wind gusts and short days of daylight, Harbin is a revelation, a place where the light of collective aesthetic joy is experienced by 800,000 visitors annually for the Ice & Snow Festival (90% from China as this is one of the country’s top winter destinations). Oddly, I kept having Burning Man flashbacks...night being preferred over day due to the psychedelic visuals enhanced by the dark, the fact that thousands of artists (15k in Harbin) labor 15 days around the clock to create something out of nothing only to know that these beautiful structures will either melt (Harbin) or burn (Burning Man), and, finally, the sense that no picture or video can capture the sensory overload of being surrounded by spectacle. Think: “You had to be there.” Remember the spectacle of the 2008 Beijing Olympics Opening Ceremony? I heartily recommend this trek that takes place late December through February.

Mellow café by day, raucous party bar at weekends, Kaffibarinn is one of Reykjavík’s quintessential nightspots. Marked with a London Underground logo on the outside, it boasts celebrity associations including Blur’s Damon Albarn (who rumor has it once owned shares in the place) and filmmaker Baltasar Kormákur (director of 101 Reykjavík, among others). Open since the 1990s, Kaffibarinn certainly knows how to throw a party, especially when tables and chairs are pushed aside to create a makeshift dance floor and local DJs (and the occasional live show) make the crowds go wild.

Great design is everywhere you look in Denmark—in shops, in homes, in public spaces—and the creativity of its people has long been a source of national pride. This museum, located just around the corner from Amalienborg, was founded in 1890, many decades before midcentury modern became an international sensation. It looks at the history of Danish design over the centuries, taking in everything from furniture to fashion to textiles.

A local favorite, Handlebar J Restaurant and Saloon has been owned and operated by the Herndon family since 1975. There’s live music every night of the week—including The Herndon Brothers Band every Wednesday through Saturday—and free country-dancing lessons Wednesdays at 6:30 p.m. Still, one of the coolest things about the Handlebar is the collection of hats that hang from the rafters, placed there by all the cowboys who have moseyed through since the 1960s.

Kennedy Park is located in Coconut Grove, right on the water with a view of the open bay, an outdoor gym including a green ladder you can climb up and down, a running path on an outdoor track, and a children’s play area. Looking to relax afterward? Grab a frozen lemonade or piña colada from the A.C.’s Icees truck or relax on a wooden dock by the water.

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?