A Fun-Filled 2 Day Pittsburgh Itinerary for First Time Visitors

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Putting together a Pittsburgh Itinerary was much easier than expected! It’s is a unique, underrated city with so much to offer! Pittsburgh is lively and vibrant with cool museums, a fantastic food scene, and stunning surrounding areas. It’s also a big enough city to keep you busy and entertained, but has that small city feel of charm in the air and there’s lots of places within walking distance.

I visited Pittsburgh for the first time a few years ago and I can’t believe it’s taken me this long to write a post about it. Because, let me tell you, we had an ABSOLUTE BLAST in Pittsburgh. My friend and I decided it was a perfect weekend road trip destination that we had to check out. We put together our perfect Pittsburgh itinerary and over the course of two days, we covered some serious ground! We truly found the best of what Pittsburgh has to offer and I’m so excited to share it with YOU!

In this post, I will outline our Pittsburgh itinerary and show you exactly how we spend our two days gallivanting around this fun city. I can promise by the end of it, you will be ready (if you’re not already) to make the trip yourself.

Table of Contents

Getting to Pittsburgh

Somewhere on the road from Buffalo to Pittsburgh

Pittsburgh is a very accessible city to travel to because of where it’s located. It’s in close proximity to New York State, Ohio, West Virginia, and Maryland as well as dozens of cities. Below I will list some cities with close radiuses to Pittsburgh, making for an ideal weekend visit or road trip idea:

Buffalo,NY– 215 miles, 3.5 hour drive
Cleveland, OH– 135 miles, 2 hour drive
Columbus,OH– 185 miles, 3 hour drive
Washington DC– 240 miles, 4.5 hour drive

Looking for other US Guides & Itineraries? Check these out too:

Pittsburgh Itinerary: Day 1

Plan Your Arrival for Pittsburgh

Depending on where you will be traveling from, plan your arrival time for Pittsburgh to be in the early afternoon. You’ll want to have a full-day so that you can make the most of your time without rushing. That way you can really enjoy the day!

Have Lunch at Mediterra Cafe

First stop on our Pittsburgh itinerary is Mediterra Cafe, which has multiple locations. Depending on where you are driving in from, you should be able to hit one of them on your way. Mediterra Cafe is super charming with coffee drinks, baked goods, as well as a full menu of well thought out breakfast and lunch options. There’s tons of seating and the one we went to even had a really cool bar right inside of the cafe. You know, in case the coffee or tea just isn’t doing it for you. I recommend saving room for a little something sweet, which you can grab on your way out.

Locations: 430 Beaver St./ 5202 Butler St./ 292 Beverly Rd.

Cost: $10-20 per person

Check out the Most Unique Place in Pittsburgh: Randyland

From lunch, drive over to Randyland, the quirkiest, most unique place in Pittsburgh! Randlyand is an outdoor art museum located on the North Side of the city. It’s colorful, vibrant, pretty weird, but also fascinating.

Randy Gilson started Randlyand in 1995 when he purchased a few run down buildings and over time he turned it into the incredible art center that you see here today. It’s open mostly everyday and it is free to enter, but donations are welcome. If you’re lucky, you might even get to meet Randy himself!

Location: 1501 Arch St.

Cost: Donation Based

Experience the Best Views of Pittsburgh from the Duquesne Incline

For a little taste of history along with the most breathtaking views, The Duquesne Incline is one stop you do not want to miss on the Pittsburgh itinerary. The Duquesne Incline is a funicular railway that’s been operating since 1877! Scaling Mount Washington at a steep 30-degree angle, this ride will take you up to the top where you’ll have panoramic views of the city skyline and its three beautiful rivers. There’s also some really interesting history that you can read up on while you’re up there.

Location: 1197 W Carson St.

Cost: $5 for a round-trip ticket. Please note, it is CASH ONLY

Check into your Hotel

By this time, you should be able to check into your accommodation. We chose to stay at Courtyard by Marriott Pittsburgh Downtown which was a wonderful experience. This 3-star hotel is in the most perfect location, with tons of great stuff within walking distance. It’s very clean and modern with helpful, welcoming staff, and it’s also very affordable! If you’d like to book your stay, click here.

Location: 945 Penn Ave.

Cost: Ranging around $200 a night

Grab Drinks and Apps at Bridges & Bourbon

After getting settled into your hotel for the evening, walk over to Bridges & Bourbon. This is the perfect spot for a little pre-dinner cocktail and appetizer. The vibes are very classy and chic, yet cozy and welcoming. There’s a gorgeous bar, beautiful dining area, and even outdoor seating. We chose to sit at the bar and enjoyed watching the talented bartenders craft our drinks. The small plates are perfect for sharing and there’s tons of fantastic, delicious options.

Location: 930 Penn Ave.

Cost: Averages $30 per person (for drinks & apps)

Have Dinner at Nicky’s Thai Kitchen

Next on our Pittsburgh itinerary is Nicky’s Thai Kitchen for a meal you will struggle to forget about! We knew it was going to be good when we walked in to a mob of people waiting. But let me tell you, it was worth the wait! The menu is extensive, filled with mouth watering currys, colorful appetizers, and tons of fresh ingredients in each traditional dish. There’s plenty of vegan and vegetarian options as well. We ordered multiple things to share and there was not a bite left on our plates. Plan to walk in hungry, and expect to walk out a little uncomfortably full, but VERY satisfied.

Location: 903 Penn Ave.

Cost: Averages $20-$30 per person

Pittsburgh Itinerary: Day 2

Have Breakfast at Caffe Mona

After a nice easy morning at your hotel, get yourself ready for your second fun-filled day in Pittsburgh. Start your day at Caffe Mona for breakfast. Caffe Mona is colorful and vibrant with a great menu and excellent, quick service. They seem to be quite known for their crepes, so of course we had to try one of those! Along with one of their omelets, which was also fantastic.

Location: 4200 Penn Ave.

Cost: $10-$20 per person

Walk over the Andy Warhol Bridge to the Andy Warhol Museum

From breakfast, prepare yourself to experience one of the many impressive museums that Pittsburgh has to offer. The Andy Warhol Museum is one that should absolutley be on your Pittsburgh itinerary! Andy Warhol was actually born in Pittsburgh, a fact that I didn’t know before visiting. This museum holds the largest collection of his work and materials. The best way to get there, in my opinion, is by walking over the Andy Warhol Bridge, where you’ll also get really cool views of the city and Allegheny River, while getting your steps in for the day.

Location: 117 Sandusky St.

Cost: $25 for adults

Tour the Famous Frank Lloyd Wright Fallingwater

After you’ve gotten your culture fill for the day, it’s time to depart Pittsburgh and drive to one of the COOLEST places in Pittsburgh’s surrounding areas. This final stop was actually what we based our entire Pittsburgh initerary around doing and is somewhere that should absolutely not be missed when visiting Pittsburgh.

Frank Lloyd Wright Fallingwater is an architectural dream. It’s not only a historic landmark, but it is quite possibly one of FLW’s most famous, well-known designs. The house was designed as a weekend home for the Kaufmann family and was built partly over a waterfall, which is the center focal point of the home. We took a guided tour, in which our tour guide walked us through the property, the history, and all of the interesting details that make Fallingwater so special. No picture truly does this place justice. Do yourself a favor and visit!

Location: 1491 Mill Run Rd. Mill Run, PA

Cost: $36 ticket for the Guided Architectural Tour

Enjoy Your Time in Pittsburgh

If I’m honest, I didn’t really know what to expect from Pittsburgh. But I left there with such a wonderful experience under my belt and truly enjoyed it as a city and as a fun weekend-getaway destination. I hope this post gave you some great insight as to what to put on your Pittsburgh itinerary and if you have any questions or comments, feel free to leave them below! Happy travels.