When I first came to Amman in the summer of 2007, I naively announced to my new colleagues how much I loved walking. I realized my folly that same day, when I had to trudge up—with less-than-great lungs and a heavy laptop bag—one of the great big flights of stairs that connect Amman’s old neighborhoods. Over the next year, I realized that walking in Amman isn’t like walking anywhere else: it means going up hills, walking down hills, trying to maintain your footing on a crumbling set of stairs.

Still, walking in Amman—regardless of the literal uphill battle—can be incredibly restorative. It’s a city with a beautiful, surreal skyline of white-stone houses. Take one corner and you’re in Philadelphia, the ancient name for Amman; take another and you’re in a market pondering the merits of sparkly shoes. Where else will you come across kids smoking shisha near the steps of a Roman amphitheatre, or find a coffee stall (not Starbucks!) at every ten paces, or one of the world’s largest flags (on one of the largest flagpoles), following you almost everywhere you look?

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My favourite walk goes through Amman’s main downtown district, combining parts of the city’s untouched neighborhoods with its tourist attractions. My favorite time to walk in the city is a couple of hours before sunset, when the heat is bearable and the sun seems to light the city from the inside.

Start with a sandwich
Begin your walk at Amman’s First Circle, the first of the city’s eight navigational traffic “circles” or roundabouts, and leads to a bunch of streets that all go to downtown Amman. Start off on Rainbow Street. While the street went through an overhaul in the late 2000s and has lost its place as Amman’s go-to hip neighborhood (that’s now Jabal al-Weibdeh, home of sidewalk cafés and hipster beards), it’s now mostly shisha cafés. But there is only one really good reason to walk this street: Falafel Al-Quds, home to what are arguably the city’s best falafel sandwiches. Once you’ve had a sandwich—or two—walk up to one of the viewing platforms for your obligatory photo with the Amman skyline as a backdrop, then walk down the stairs just before the platform onto Shukri al-Shasha Street. (There’s a parking lot that serves as a better viewing platform.) Keep heading downwards. Stop by Shams el-Balad, the best of Amman’s hipster cafés, which will make you a believer in brunch with its flatbreads, salads, and use of seasonal produce. (Just give in and order the entire menu.) Get onto Ameer Muhammad Street, and you’ll slowly head into the heart of downtown.

Amman doesn’t really have the sprawling markets of other capitals in the region; the side streets and old buildings constitute its own version of a downtown district-meets-get-everything-bazaar. But what it lacks in historic gates and hustling shopkeepers, it makes up for in the way the city seems to bring everyone together. In the evenings, Amman residents head downtown to shop, eat, and to smoke shisha in the balcony cafés that overlook the main roads. A 1973 Associated Press article detailing a gunfight in an Amman cabaret dismissed the city as a place that shut down at 8 p.m. While Amman still isn’t particularly nocturnal, it’s far from boring. A pre-recorded chant of “fadal amara, dinarain o aktar”—“enter the shop, [everything] is 2 dinar and above”—blares from clothing stores. As you walk down Amir Muhammad Street, pause every five minutes to take in all of Amman’s oddities: the cat seated on a chair on a pavement, or the stairs with a canopy of umbrellas and crowded with selfie-seekers and posing couples, the stores selling “maid uniforms”, which is a thing in Amman.

After a few minutes of wandering around, you’re bound to be hit by the smell of deep-frying carbs emanating from Hashem, Amman’s beloved 24-hour restaurant, were you can finally taste real hummus and cry over the pumpkin-infused imitations you’ve been forced to eat for so long. Join the crowds outside the dessert shop Habibeh, where people take their knafeh—cheese pastry soaked in syrup—to go, eating it off plastic plates as they stand outside. Head into the side streets and ask around for the Pakistani restaurant, where you can get a cup of Kashmiri-style tea. Walk towards King Faisal Square and past Amman’s historic buildings—the Arab Bank, the Duke’s Diwan—and take in the displays of belly dancer costumes in tourist trap shops. Stop by Balad al-Rasheed (in English, the Eco-Tourism Café), an old shisha café with a balcony wall painted with flags.

Roman Holiday
Head to the Al Husseini Mosque, one of Amman’s landmarks. On Friday afternoons, this is where protesters gather to begin their marches through downtown; most days, the mosque courtyard is packed with people heading to worship, and you can buy everything from charging cables to prayer beads from street vendors. Since I have an abysmal sense of direction, the mosque is how I orient myself: on the right to the mosque are the markets where you can buy everything from bags of chamomile to tomatoes, and blessedly, a grocery that stocks mixed pickles from Pakistan. Take a left, and you’ll come across the ruins of the Roman Nymphaeum. Tucked around the corner of the ruins is the Mahall al-Maa bookshop, which is possibly one of the most fascinating places in Amman. The shop—which is open around the clock—feels more like a library than a store; more of a literary experience than a book buying errand. Customers are encouraged to pay what they feel like for their selections, and the racks are stacked with books dating from the British colonial administration in Palestine. Contemporary novels are mixed in with books that seem to be there to make a point about being unfettered by the chains of self-censorship and bestseller lists. I once walked past, and ended up spending the entire evening at the bookstore talking about Arabic and publishing.

Once you’ve ripped yourself away from the bookstore, walk down the road to the Roman Amphitheatre. Grab a coffee from the shop next to Gate D—they add a dose of condensed milk to instant mixes—and walk around the expansive Hashemite Plaza. Stare at the amazing sight of a theater embedded in the city’s landscape, surrounded by Amman’s urban sprawl, almost as if the houses were built first, and the theater later. I’m constantly fascinated by how the theater continues to live as a space in the city, not just an edifice for tourists.

Step on it
Head towards Jabal al Qalaa, home to the Citadel and the ruins of a temple dedicated to Hercules. Downtown Amman is connected through a series of winding steps cut in the hills to help one get around without having to walk long distances, and as shortcuts between neighborhoods. While you can take a set of steps going up the hill, the walk is far more interesting. Walk past the amphitheatre and the Raghadan terminal. Get on the flyover—don’t be scared, there is a pedestrian sidewalk—and when you disembark, you’ll find yourself on K. Ali bin al Hussein Street, opposite the gates of the Raghadan Palace and the Royal Hashemite Court. (If monarch memorabilia is your thing, visit the Royal Automobile Museum near Seventh Circle for the incredible collection of cars owned and used by the late King Hussein).

Up the hill
The stretch of road might seem unassuming; there are ironworkers and printing presses, the ubiquitous coffee stalls, and more flights of stairs leading up to people’s homes. But as the road slopes upward, heading all the way to Jabal al-Qalaa, you start to get a sense of how the city was built around the hills. As you walk up, take a moment to pause and look at the city from here: the views of traffic, the light playing off the buildings, the birds flying overheard, the cat digging into a garbage bag. This is why I love walking in Amman: you experience the city from (literally) multiple levels, and see parts of the city that haven’t been paved over with marble and turned into postcard-perfect versions of their earlier selves.

When the border walls for the Citadel come into view, take a left and go down the road, which will take you right back into downtown. Emerge onto the street, slightly damp from your labors, dizzy from all the things you’ve seen and the loop around the hills. Now you can have some well-deserved knafeh.