The good news: Pittsburgh is compact. The bad news: It’s built on a wedge, surrounded by two rivers. There’s no easy grid to get around. You’ll likely rely on uber/lyft; our buses are not easy to learn to use.
First, be sure to enjoy the view of Pittsburgh’s skyline as you enter the city from the airport, emerging from the Fort Pitt Tunnels. You can enjoy this view at your leisure too from atop the hill the tunnels pierce, Mount Washington. You can take our famous incline to the top from down below. The station is located near a dull mall, Station square.
Friday night: The Andy Warhol Museum is half-off, just $10 to visit this shrine to the creator of Pop Art. It’s the largest museum in North America dedicated to the work of one artist. It was renovated two years ago for its 20th anniversary. Should you not have time to visit, each Friday evening is Good Fridays—a happy hour in the Factory-themed silver lobby that is free to attend (though sadly the drinks are not). Current featured exhibition, from the Perez Museum in Miami: http://www.warhol.org/event/firelei-baez-bloodlines/
The Museum is on the north shore. There are many bars and restaurants there, though none I’d really recommend for a unique experience. However, you’re one bridge away from downtown, and perhaps a mile and-a-half from the Strip District.
Downtown has many great restaurants. For an inexpensive and filling meal, try Emporio for a meatball sandwich and a beer. For a more upscale experience, take the lift to the 2nd floor for wood-fired pizzas at Mezzo; if the weather is agreeable, the third floor is a fun rooftop pub, Il Tetto, modeled on Eaterly’s Baita.
The Strip District is a must weekend visit. These few blocks where were food was trucked in and unloaded—and, as you might have heard, home to Primanti’s, which served large meals to busy truckers, between two slices of bread. (I wouldn’t waste a meal there; it’s more a novelty.) The Strip has more commercial offerings now. Avoid the snobby 21st Street Coffee (their motto should be “Have it Our Way) and instead visit the charming granddaddy of Italian espresso shops, La Prima (which actually IS on 21st Street).
Is it warm? Perhaps Lucy is back from her annual winter trip to her homeland in Vietnam. Lucy has been making the city’s best sandwich, on a gas grill on Penn Ave. near 18th Street, for decades, long before we knew to call them bahn mi.
How early did you hit the Strip? Was it very early, around 8am? If so, an Uber will get you to the South Side’s Carson Street in time for the 10am kickoff of several Premier League matches at Piper’s Pub, where you’ll be met with conviviality and a very good pint of Guinness. Should you choose to eat there, the food is good, honest, large, and very reasonable. I’d do the raised waffle and fried chicken, which would almost certainly get you through to dinner….
(Or, perhaps you’re an early riser, and made it to Piper’s in time for the early match, which starts at 7:30am, in which case I’d recommend the Scotch Eggs.)
Is it baseball season? Are the Buccos in town? You should catch a game at PNC Park, the loveliest in America, with wonderful views of Pittsburgh’s gem of a skyline.
The South Side: unless there to watch Chelsea thrash a Premier League opponent, I’d say skip it, especially at night, when the region’s youth descend on it for drunken debauchery. (Though you may like that sort of thing?) In the evening something a little more rarefied is called for. Do sit at the bar at Union Standard—brand new, but great legacy. Share a few appetizers at $6-$12 each with a good beer or glass of wine.
The new regional darling is Lawrenceville. Get the best espresso of your life at Espresso a Mano, an then meander down Butler Street, stopping at galleries, pinball joints, and bars, for a hot dog at Franktuary.
Also on Butler, next to a movie house and beer bottle shop, is probably the restaurant I’d choose to eat in above all others, Smoker Taqueria. Cash only. But don’t get an appetizer, you’ll be too full to experience the wonderful tacos and mac and cheese, the best I’ve ever had.
Sunday, come to Oakland, in the city’s east end, Oakland. While waiting for the Carnegie Museums of Art and Natural History to open at noon (get both for $19), walk through the University of Pittsburgh’s Cathedral of Learning. You can’t miss it. (Free.) For decades it was the tallest educational structure in the world. Don’t miss the glorious gothic Heinz Chapel on its grounds (also free). The Carnegie Library is also a splendid building, located next to the Museums. (Free.)
The Museum has a wonderful new Carnegie Café, which now serves a good brunch on Sunday. The coffee is excellent. In Oakland there are some fun dining options. I’d recommend Spice Island, walking distance from the Museum.