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Petra flourished more than 2,000 years ago, trading with Rome as an equal before being abandoned after a series of earthquakes in the 4th and 6th centuries C.E. It wasn’t until the 19th century, when European explorers “rediscovered” it, that the ancient city returned to the public consciousness. Now, visitors can walk down the narrow canyon of the siq to the city entrance—as dramatic an approach as any to a tourist attraction on the planet. The canyon opens up onto the carved facade of the Treasury, Petra’s most iconic site. From there, you can explore the cliffside tombs with their colorful bands of sandstone, the Street of Facades, and the amphitheater hewn from living rock. The ancient center lies some distance off, along with the splendid old Monastery, which sits at the top of a steep but rewarding climb. Consider buying a three-day ticket and visiting at different times of day to enjoy the changing light—early in the morning is best for the Treasury, while late afternoon is better for the Royal Tombs.

A hotel with the words “gallery” and “art” in its name would be remiss not to include at least a nod to the art world in its decor (though more than a few establishments have been known to throw up a wall-sized painting by a well-known artist and declare themselves art hotels). As Florence’s pioneering design hotel, the Gallery Hotel Art doesn’t skimp. Virtually the entire ground floor, from the lobby through to the lounge and trendy Japanese-Mediterranean-Peruvian fusion restaurant, is one giant gallery, its sleek white decor acting as the calming, understated counterpart to the contemporary art and photography not often found in this city.

Indeed, don’t underestimate the groundbreaking nature of this hotel. Design hotels may be a dime a dozen these days, but when the Ferragamo family’s Lungarno hotel collection launched with this modern getaway designed by Michele Bönan, its clean-lined furnishings and chrome, white, and natural wood hues were a challenge to a city outfitted in rich brocades and dark wood antiques. As such, the Gallery Hotel Art isn’t the flashiest stay, but it is the kind of place you can relax and unwind and feel like you aren’t living in the Renaissance days.

A 1920s townhouse in Brussels’ well-heeled Châtelain neighborhood, the intimate, Fellini-inspired Odette en Ville might as well be your fashionable Belgian friends’ pied-à-terre in the European capital. Its older sibling, Chez Odette, a landmark restaurant and inn, is hidden away in the tiny village of Williers, on the French-Belgian border, and when the Brussels iteration opened, it dressed up with all the panache of a newer arrival: a little bit flashier, a little bit sleeker, a little bit more urbane. Its marble bathrooms, dark walls, and chrome accents all feel very grown-up, but roll-top tubs, fireplaces, and vintage decor reveal those homey country roots, as does the fresh, unpretentious cuisine, including the homemade jam at breakfast. With just eight rooms, the hotel feels intimate and private, an atmosphere only enhanced by the private library, a cozy lounge (notably, adjacent to the bar) with overstuffed leather Chesterfields, vintage chess sets, shelves of art books, and a working fireplace.

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.

Put on your comfortable shoes and head to the many trails of Cayman Brac to see wildlife, as well as scenic and geological sights. There is a path for all skill sets. Listen to the mating calls of the parrots flying above at the National Trust Parrot Reserve Hiking Loop, or descend carefully into Peter’s Cave and move through the various layers to discover a truly breathtaking natural wonder. Most hotels have a brochure of all the hiking trails; this includes images, difficulty, and a brief description of each trail.

A staple among Upper East Side hotels since it opened in 1963, the sophisticated Loews Regency boasts a Park Avenue address and location convenient to Central Park and Manhattan’s best museums. Following an extensive renovation, it reopened as a fresh and chic retreat in early 2014. The bones of the hotel remain classic, but the approach is modern, with touches that today’s traveler will appreciate, such as free Wi-Fi. Its elegant lobby—with a striking art installation from Brooklyn artist Nina Helm—impresses with its 24-foot ceilings and the on-site salon and spa, from acclaimed hair stylist Julien Farel, is a neighborhood destination for visitors and locals alike. No classic New York hotel would be complete without a standout watering hole; you’ll want to order a cocktail at the low-lit Regency Bar.

There aren’t too many opportunities in the Caribbean to ride on horseback to a cave. In Los Haitises National Park, located three hours west of the resorts of Punta Cana, Fun Fun (pronounced “Foon Foon”) Cave is officially known as the largest cave in the Caribbean. Though the cave itself is in the National Park, access to the land goes across a private ranch and requires a guided tour. While the nearly three-hour drive from the resorts of Punta Cana is a lengthy, bumpy, journey into the interior, the scenes from the window provide an authentic glimpse into rural Dominican life. Sugar cane sways, schoolchildren wave, and mangoes drip from the trees. Upon reaching the ranch where you begin the tour you are shimmied into a jumpsuit and saddled onto your horse. A 45-minute ride through the shaded forest brings you to the edge of the National Park. From here it’s another 30 minute walk through sun-swallowing trees until you reach the entrance of Fun Fun Cave. Sliding into a harness and climbing gear, entering the cave requires a 50 ft. repel into a tiny hole which can barely fit your shoulders. Once at the bottom, it’s a one hour slog through the depths of the darkness before reaching the other exit. Inside the cave, stalactites and stalagmites pepper the areas which fall in the beam of your flashlight, and at some areas you are forced to swim through the soothing, subterranean waters. Here, a lone rope helps guide visitors through the hidden recesses of the cave.

Italy’s No.1 chef Massimo Bottura described Nottingham Forest as a blend of “Hemingway and the TV show C.S.I.” for its eclectic vibe. But for its cocktails, Bottura and many others feel Nottingham Forest is Milan‘s main innovator. Mixologist Dario Comini just happens to be considered one of Italy‘s best bartenders, thanks to a great mix of creativity and risk.

Eating raw herring is a right of passage for many who visit Amsterdam. Order yours from the friendly Dutch matrons in blue and white-striped aprons at Stubbe’s Haaring, a herring stand with a view on the bridge over Singel Canal, just off Haarlemerstraat. For decades, this local institution has satisfied the fish cravings of Dutchies and visitors with lightly brined herring, smoked eel and other delicacies from the North Sea. Unless you want bragging rights, there’s no need to eat your buttery snack Dutch style, grabbing it by the tail, throwing your head back and lowering the fish whole into your gaping mouth. Most locals eat it in a less flashy way: cut up into small pieces, covered with onions and sweet pickles, topped with a Dutch flag. It’s served on a waxed paper plate, sans bread or cutlery. Use the flag-festooned toothpick to stab the soft, mild-flavored morsels and bring them to your mouth. For a more filling meal, order a broodje haring (herring sandwich) on a soft, white bun, filled with fish, pickles and onions. Eet smakelijk!

Upon first entering the famed blue doors of Per Se, located inside the Time Warner Center overlooking Central Park, the dining room has the air of a wake, filled stiff collars and hushed tones. But no matter the attitude, the fact is that everyone in the dining room waited at least a month for this moment. At Per Se, you can only make a reservation one month in advance (maximum), and, if you procrastinate a day or two (say 28 or days or less before your desired date) you’ve likely missed your chance. (Do take note that you cannot cancel a reservation within seven days without being charged $175 per seat reserved.) This is an experience that will last up to four hours, where you are served from five to nine courses (depending on the menu you select), with many surprises in between, including personalized menus with your name and event (if you’re celebrating anything) on each. Now, if you’re still interested and not frightened away by the potential cost, then you’re in for an amazing afternoon or evening of small plates with the most amazing tastes you’ll ever come across. Do not be deterred by the portion sizes as you will most certainly leave full. It might even be best if you arrive on the borderline of famished, as it is a crime to leave anything behind.

Botswana’s most famous crafts are baskets woven from fan palm fibers. They are dyed with natural pigments: blue from fever-berry leaves, dark brown from magic guarri shrubs, and yellow from the roots of red star apple trees. Some baskets take a month to make. Nearly all lodges sell baskets, but you can also purchase them online.

This is my favorite hike by far. Cueva Ventana (“Window Cave”) is a beautiful, scenic hole in the side of a mountain that opens up to a lush, green valley down below. You’ll trample through mud, hunker down under low-hanging stalactites, dodge around stalagmites, and never look up (there are bats, of course) while wandering through the cave. All this winding around through two caves leads you to one of the most spectacular views in all of Puerto Rico (but I may be biased). The hike to this cave is half the fun. You climb down into a small opening under enormous, ancient tree roots, and you get the feeling of a tomb raider. But, if you’re claustrophobic or don’t feel up to lowering yourself down a cave wall, there’s an additional path that bypasses the first cave and leads you straight to the easier hike to Cueva Ventana. There’s something for everyone! I’m pretty sure I saw one Puerto Rican woman doing the whole thing in heels. This is a must-visit site for anyone touring the northwest central part of Puerto Rico. Another tidbit is that it’s practically free! You can find the directions on PuertoRicoDayTrips.com, park at the adjacent Texaco gas station. UPDATE (2014): There is now an easier way to access this awesome view! There are now boardwalks for ease of access, and you must pay $11 to tour the site. You get a flashlight and hardhat for safety.

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.

One of my favorite dive sites on the west coast of Puerto Rico is Crashboat in Aguadilla. This shore dive is easily accessible for all levels of diving, and you’re guaranteed to see something amazing on this artificial structure. Crashboat is named for this once Air Force based marina, where the “crashboats” would deploy to retrieve the crashed planes from training sessions of Air Force pilots. It was later abandoned and turned into a recreational area for locals and dive enthusiasts. Scout the pilings for seahorses, frogfish, octopi, and lionfish. At maximum depth of 30 feet, find a sunken base where bigger fish like to hide. Bring your flashlight to scope out the interior. Not a diver? No problem. Enjoy the sandy beaches, reggaeton music, and aromas of delicious Puerto Rican food all day long. One entire side of this recreational park is lined with street vendors selling food, handicrafts, and drinks. Want that true Puerto Rican vibe? Want to see how the locals relax on a weekend? Crashboat is your place. But if you’re not interested in the crowds, come here in the morning on a weekday. I dive here regularly, and I avoid crowds by diving early. Enjoy!

If you’re into trains (or your kids are) this museum is a ferroequinologist’s (a person who studies trains) paradise. This museum houses over 100 steam and diesel locomotives, passenger cars, and cabooses as well as a G-scale model railroad in its 15-acre rail yard. There is also a restoration facility and working round table that will wow curious minds and train fans.