48 Hours in Pittsburgh

“Pull up a chair. You are welcomed here.”

Never have we ever connected to a city’s slogan more than in Pittsburgh. When we think of a city that embodies acceptance, community, and friendliness, Pittsburgh is instantly the city that comes to mind.

From the friendly couple that we met at a brewery on our first night, to the chatty college student we sat next to at Primanti Brothers, to our artsy barista at Constellation Coffee, there’s something different about this city. And we’re convinced it’s the people. They instantly feel like family, making Pittsburgh instantly feel like home. It’s incredibly special.

But beyond the friendly locals, Pittsburgh is also an incredibly beautiful, progressive, and fascinating place. So much so, that we’re already looking for an excuse to go back. But in the meantime, we’ll reminisce and look at pictures and guide you to our favorite spots in “the Burgh”. Here’s where to go if you only have 48 hours!

Obsessed with the City of Bridges!


Coffee at Espresso A Mano: You know a coffee shop is good when there’s a line out the door. Don’t let the line deter you, it moves fast - and the coffee is worth it. Grab a vegan donut while you’re there, too.

Breakfast sandwiches at Pear and the Pickle: We take breakfast seriously, and breakfast sandwiches even more so. The ones at Pear and the Pickle aren’t fancy, but they’re melt-in-your-mouth good. And you can play board games while you wait for them, which is a win-win in our book!

Take a ride on the Duquesne Incline: Voted one of the “Top Ten Sites in the World for Viewing a Cityscape” by USA Today, the 140-year-old Duquesne Incline not only offers picture-perfect views, but it puts the ‘fun’ in funicular! And the ride is dog-friendly, too! ($5 round trip for adults, $2.50 for kids. Don’t forget to bring cash - it’s cash only!)

Visit Randyland: Most artists wouldn’t be willing to open their private courtyard to the public, but Randy Gilson isn’t like most artists. Everyday from 10am-7pm, visitors are welcome to explore his many eccentric art displays around the property, and if you’re lucky you’ll get to hear from Randy himself!

Walk the Strip District: Located on the banks of the Allegheny river, just outside of downtown Pittsburgh, is the popular shopping and dining neighborhood The Strip District. This revitalized industrial neighborhood is packed full of international grocery stores, independent merchants, local retailers, shops, restaurants, and more. Make a stop at the Second Floor Bar at The Pennsylvania Market for a cocktail or two, and maybe even a slice of pizza! (It’s gooood.)

Catch the sunset at Point State Park: Take an early evening stroll around the tip of Pittsburgh’s “Golden Triangle” at the stunning Point State Park! You’ll have a panoramic view of the city, and there’s no better place to be at sunset!

End the night at Grist House Brewery:  Rotating food trucks, solid craft brews, and a dog-friendly outdoor area, we’re big fans of this spot. Grab a seat at one of the many picnic benches outside, and be prepared to make some new friends!

Incredible breakfast sandwich at Pear and the Pickle

The Duquesne Incline!

Amazing view from the top of the Duquesne Incline

Lovely afternoon at Randyland!

Randy himself!

Yummy pizza at the Second Floor Bar

Hanging at Point State Park

Sally loved Grist House!


Coffee at Constellation Coffee: This small, cozy coffee shop is a little off the beaten path (in the Lawrenceville neighborhood), and that’s exactly why we like it. It’s a local’s spot with strong coffee and knowledgeable baristas.   

Grab a juice to-go at Pittsburgh Juice:  Still thirsty? Make a stop at Pittsburgh juice, where you’re sure to find a healthy, satisfying, and organic juice or smoothie. (One of our favorites is the Green Goodness.) Cheers to your health!

Tour The Andy Warhol Museum. Did you know that the pop art icon Andy Warhol was born and raised in Pittsburgh? We didn’t either! The Andy Warhol Museum tells Andy’s story and explores his legacy through his personal art collection, archives, and more. Guests can even star in their own short film, inspired by the Screen Tests Warhol created in the 1960’s!

Try the iconic sandwiches at Primanti Brothers: “You can’t go to Pittsburgh without getting a sandwich at Primanti Bro’s” - every Pittsburgh local. And they’re right. Stuffed with house-made coleslaw, fresh cut fries, tomatoes, provolone cheese, and your meat of choice, it’s a sandwich experience unlike anything we’ve ever had. Extra props if you can finish it!

Walk the Bridges: Known as “The City of Bridges”, Pittsburgh is full of them (446 to be exact). You’ll need to walk off your Primanti Bro’s sandwich, so we recommend crossing oer the Alleghany River at 6th, 7th, or 9th street. Each of those bridges (the Roberto Clemente Bridge, the Andy Warhol Bridge, and the Rachel Carson Bridge) are beautiful and open to pedestirans. They make for a great photo opp, too!

End the night at Tako: Elevated tacos with a global twist, Tako is unlike any taco shop we’ve ever been to. From the decor to the spices, it’s original and it’s exotic. With raving reviews from Zagat, Thrillist, Eater, and more, visitors will definitely need a reservation. Make sure you try their famous Korean Tacos!

One of our favorite pieces at The Andy Warhol Museum

There are 446 bridges in Pittsburgh. How many can you visit?

*This list should keep you very busy during your 48 hours in Pittsburgh. Note that we tend to move quickly when we’re in a new destination. So you might want to cut back or simplify this list as you see fit. And be sure to leave a comment with your favorite Pittsburgh spots, as we’re sure to be back soon!