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AFAR chose a destination at random—by literally spinning a globe—and sent comedian Jorma Taccone on a spontaneous journey to Nairobi, Kenya.

The best way to hop between popular tourist sites is to hitch a ride on one of Tumon’s ubiquitous open-air trolleys. Trolleys make stops along Hotel Row in Tumon, as well as at select locations in downtown Tamuning and Hagatna, including Two Lovers Point and Chamorro Village. Not only are trolleys among the only forms of public transportation available on Guam, they’re also a pleasant way to explore the island.

Get swept up to the top of a peak, meditate in a monastery garden, and ride a ferry through a light show all in the space of a single day in Hong Kong. This busy city offers visitors sometimes startling contrasts: a hike along a rugged hilltop trail can transport you to a view of the shimmering, modern skyline that will knock whatever’s left of your breath away. Wander densely populated streets and then find yourself on a quiet length of shoreline. Welcome to the most cosmopolitan and thrilling city you may ever visit.

While there are a number of ways to cross the Huangpu River, the most scenic is—without a doubt—by ferry. Part of Shanghai’s incredible public transportation system, a couple yuan will get you from one bank of the river to the other, with a view to boot. Ferries run every 15-20 minutes depending on the time of day and take off from various ports on either side. Check out the link below for more details.

The Artmore is one of the few independent boutique hotels in Atlanta. The 1924 Spanish Mediterranean style hotel has been renovated and is strategically located to public transportation. The modern décor is present in guest rooms as well as the Studio Bar and Lounge. The plush outdoor lounge would look at home in Miami. In addition to standard one and two bed guestrooms, the Artmore has loft suites for guests staying for extended periods of time.

The second most famous public sculpture in Chicago is 50ft high, made of steel and no one knows what it means. It’s doesn’t even have a proper name so it’s just known as “The Picasso.” Pablo Picasso gifted this untitled sculpture to the city of Chicago in 1967 and it caused a big ruckus because, well, it’s weird looking and no one knew what it was supposed to be. A woman? A chimera? A face? Hard telling. We do know that it was the first modern sculpture installed in the downtown area and it’s now the pride and joy of Chicagoans and photographed almost as much as the Bean. On sunny days you’ll see kids sliding down that sloping steel base and I love that the city still allows those jungle gym antics on such famous real estate.

Founder’s Note: Uncommon Travels

Union Station is as stunning as it is rich in history, and continues to be a vital hub for L.A. rail, metro, and bus transport. On the outside, the building resembles an art deco riff on the old California missions; inside, the inlaid travertine and terra-cotta floors show the sort of detail work so rare in modern depots. Local tip: Settle into one of the giant leather chairs in the cavernous waiting room and immerse yourself in the city’s seedy side with Chandler’s noir classic, The Big Sleep. (Without a ticket you can’t enter the waiting room, but you can at least enjoy the Navajo patterning on the station floors.)

In the city’s once-gritty fishermen’s quarter, a group of activist chefs is reviving—and reinventing—traditional cuisine.

If eating huge plates of pork, deciphering local slang, and snowshoeing through the woods of Québec can’t bring two siblings together, what can?

Named for the Japanese word for enlightenment, this boutique property marries classic Cycladic architecture (cube-shaped structures, whitewashed stone walls, arched entryways) with the clean lines of locally made furnishings in naked wood. None of the 25 rooms and 10 suites are the same, but most have private outdoor whirlpools or plunge pools, plus plush beds that make it impossible to leave. Nearly all of the public spaces, however, offer stunning views over Mykonos (about 1.5 miles away) and the bay, and make striking use of night-lighting, especially at the pool, which is built into the natural rock face. A grottolike spa features two treatment rooms, a futuristic-looking whirlpool area, and a hammam for stylish pampering sessions. The hotel offers complimentary transportation to Mykonos, but with its inviting Bar & Sunset Lounge and a restaurant that is garnering awards and accolades, you may decide to stay put for the duration of your vacation.

San Diego’s first food hall is housed in the city’s former naval training center, a 361-acre site in Point Loma that now features a lively business district with wide lawns, a waterfront park, and historic Spanish Revival–style buildings. Here, vendors serve everything from coconut-curry chicken sausages to ahi tuna poke bowls, providing the makings of a casual lunch or dinner. Take your food to the patio, or sit inside at the high-top tables near the bar and enjoy the untouched murals that line the upper walls. Painted by naval recruits in the 1950s, they depict various vessels, from a late 18th-century sailing ship to a World War II aircraft carrier.

This sleek, ultra-modern spot takes its inspiration from the linear forms of Dutch painter Piet Mondrian. The Gezi Bosphorus offers a chic and thoroughly striking alternative to the city’s usual Ottoman aesthetic. Cozy rooms have a retro feel with smoked oak and glass used to create warm yet light-filled interiors. Floor-to-ceiling windows in the Deluxe Bosphorus rooms have attention-grabbing views of Istanbul’s iconic Bosphorus Strait.

The Gezi Bosphorus’ green credentials set it apart and prove comfort doesn’t have to be sacrificed for sustainability. Proudly practically zero-emission, the hotel reuses water in its garden; recycles all papers, plastics, and metals; and produces hot water from excess air-conditioning system energy, making it one of the city’s few hotels to receive Turkey’s Greening Hotel Certification. Just off Taksim Square, staying here puts guests amid Istanbul’s modern city core, steps from the shopping vortex of İstiklal Caddesi but still only a short hop on public transport to the historic quarter of Sultanahmet.

In a city full of burger joints, Holeman and Finch Public House stands out for its extensive drink selection and Southern twist on farm-to-table fare. Tucked into the back of an apartment complex on Peachtree Street, the popular spot serves specialty cocktails and what seems like every obscure beer, wine, and liquor that exists. In fact, H&F also owns a bottle shop, where it sells many of its rarest selections. To pair with your drink, the restaurant offers a signature burger with two patties, cheese, onions, pickles, and a side of fries. What makes it so fantastic, however, is the bun, which H&F bakes in-house and even sells to other restaurants. It was originally available only after 10 p.m. nightly or during Sunday brunch, and the restaurant once made just 24 each day. To make matters more complicated, H&F doesn’t take reservations, so it’s not uncommon to find a line out the door and a wait time of up to 2.5 hours. Plan accordingly.

Minsk, the austere capital of Belarus and a former Soviet satellite, harbors Beatles cover bands, bookish bohemians feasting on salo and vodka, and the curious legacy of Lee Harvey Oswald.