Ultimate 2 Days in Philadelphia Itinerary

brunette and blonde woman on rooftop Bok bar during 2 days in Philadelphia

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Thinking of spending 2 days in Philadelphia for a little adventure in the land where Independence Day was born?  You know, the city where people party it up like it’s the 4th of July everyday?  It’s not a complete exaggeration, as according to my sister, Philly’s newest resident, fireworks can be sighted all the time.  Or more likely, it could be because I visited in July…

Anyways, I gotta admit that before my sister lived here, Philly wasn’t super high up on my bucket list.  It’s not that I didn’t want to see it, but I had been prioritizing new states since I’m trying to see all 50. However, I now relish the opportunity to be able to see “The City of Brotherly Love” with my sister (and free lodging!).

This was my first of hopefully many visits, and I have to say I loved Philadelphia. This city exceeded my expectations on all levels with its cobblestone streets, awesome bars, and multitude of historical sights.  It was very easy to walk to many places and generally feel safe.  Philly wasn’t exactly the cleanest, but what can I say? I like a city that’s a little rough around the edges.

That being said, if you are looking for a weekend getaway in the United States and love history, 2 days in Philadelphia is definitely a must-do.  Below, I am laying out how I had an awesome time in Philly over just two short days.  I’ll be sure to point out my favorite places – there were a lot of cool spots that I had no idea existed in Philly until my trip!

mural in philadelphia - 2 days in Philadelphia

How to Spend 2 Fun-Filled days in Philadelphia

Flying to Philly

If you fly to Philly, you’ll land at Philadelphia International Airport, where it will then be very easy to grab an Uber wherever you need to go.  Just make sure you follow the signs for “Ride Share” out of the airport, as they are in a different area than the taxis.  I personally flew American to get to Philly.  There’s an American Airlines hub there, so there are many options for direct flights.

I should note, this was my first time taking a round trip flight by myself, and then Ubering alone to my sister’s apartment.  This may be a small feat for some, but with all my anxiety around flying and traveling alone, this was a big deal.  It only took me 29 ½ years!

Travel to Your Lodging

Before my visit, I had no idea that Philadelphia is actually quite large with several neighborhoods.  I was very fortunate to be staying in the Old City neighborhood, which is quiet and filled with historical character.  It took me about 20 to 25 minutes to get there from the airport in the backseat of an Uber. 

My first impression of Philly was this chatty Uber driver with a heavy Jersey accent.  Her accent had me all warm and fuzzy with memories of visiting my grandparents at their New Jersey apartment when I was younger.  Well, that is until she started oversharing about being mistaken for pregnant and lying about miscarriages to make people feel bad. Picture of class right there.

When I finally arrived in Old City, I learned how close all the historical sights were to the area.  It was a five minute walk from the apartment to the Liberty Bell, which was awesome.  It made sight-seeing pretty easy despite the crazy 100 degree weather we were dealing with that weekend.  Don’t be scared off though – Philadelphia is apparently not normally that hot during summer.

beautiful red brick building in Old City Philadelphia

2 Days in Philadelphia: Arrival Day

Stroll the Historical Area

I like to begin my first time in a new city by getting a lay of the land. A great way to do this is by taking a walking tour, and that was certainly my original plan. Thinking that both my sister and her boyfriend would be at work when I arrived, I downloaded the Self Tour Historic Philadelphia app for $5.99 to do some solo sight-seeing.

This ended up not being the case, as my sister’s BF was working from home, and ready to explore when I got there. I had no problem with this, though, since he seemed eager to go and also knew how to get to all the main sights.

brick buildings with black fire escapes in Philadelphia

Since my flight arrived around 2:30 p.m., there was still plenty of time to sightsee that afternoon.  That being said, walking for too long was misery in that stifling heat, and forgoing a walking tour was probably for the best.  What we did do was basically wander the general historical area until we were saturated in sweat.

In this process, we passed awesome sights, including the Liberty Bell and Independence Hall. Even though the city is very urban and modern, it still has a very colonial feel with cobblestone streets, brick architecture, and tour guides running all over in three-cornered hats. The only thing missing was Ben Franklin himself!

cobblestone streets in Philadelphia

Check Out a Local Bar

After some walking around, we ducked into Independence Beer Garden (you’ll see basically everything in Philly is named Independence, Revolution, Franklin, etc.).  I got a very refreshing spicy tequila cocktail, which I all but downed in thirst.

After this, we did a tiny bit more wandering, passing a cute area called Franklin Court, featuring the Benjamin Franklin Printing House and Benjamin Franklin Museum.  We also passed Christ Church, which is significant for having several Founding Fathers buried right onsite.  It was closed at the time, so we just peaked into the gates.

After some fascinating historical wanderings, it was time to head back to the apartment and freshen up before heading back out for the evening.

exterior of garden surrounding Independence Beer Garden

1st Night Out in Philadelphia

Our first stop was Standard Tap, a cool little space with a solid craft beer and cocktail list and a high quality, everchanging menu.  After browsing the options, we realized this place was slightly more upscale than we were expecting. We did end up ordering calamari to share amongst the three of us, which was small-portioned and unfried but very good and fresh.

Since cheap eats became the goal for the evening, our next stop was a Mexican restaurant for a huge pile of nachos to share.  We also split a pitcher of margaritas for washing down the ‘chos.

The rest of the night involved wandering in and out of nameless bars in Old City, playing large jenga, and trying unsuccessfully to convince DJ’s to play dirty rap music.  I drank a lot of whisky and bourbon cocktails, and we finished off with a slice of pizza on the way home for a late night snack.

blonde and brunette girl high fiving in front of old city mural
Awkwardness at its finest in Old City

2 Days in Philadelphia: Day 2

The second of my 2 days in Philadelphia was all about seeing famous American historical sights. We saved money by eating in for breakfast that morning, and then headed straight to the following places:

statue of the signer in Philadelphia - 2 days in Philadelphia

Liberty Bell

This was our first stop. A must-see in Philly, the Liberty Bell is on display in its own building.  The line goes out the door and wraps around the corner on the sidewalk.  However, it does keep moving and it honestly doesn’t take that long to get in and see the Liberty Bell and get out.  I’d say it’s worth it, since visiting is free of charge and low fuss.  We went in the morning, which is what you should do too to avoid the worst of the crowds.

Travel Savvy Tip: If lines aren’t your thing, you can still see the bell from outside through a window.

blonde and brunette girl in front of the liberty bell - 2 days in Philadelphia

Independence Hall

Unless you visit during January or February, getting into Independence Hall can be a bit trickey.  While entry is free, there are timeslots each day for the guided tours, which you can either reserve online or receive on arrival first thing in the morning.  I will tell you right now that if you wait until the morning of, you may not get in. 

We actually planned to visit Independence Hall on Sunday before my flight. Unfortunately, our 9:30 a.m. arrival was too late, and the earliest time available was 12:30 p.m..  With my flight being at 1:30 p.m., we unfortunately had to pass.  Next time, we are going to reserve in advance online.

If you cannot get into Independence Hall, you can still visit Congress Hall right next door.  This fascinating space is where the U.S. Congress would convene from 1790 until 1800.  The exhibit is small but really good, and even has a guide who periodically gives a presentation on the history.

Independence Hall in Philadelphia - 2 days in Philadelphia

Christ Church

Yet another significant historical sight, Christ Church once again has five Declaration of Independence signers buried on its property.  You can wander around the building and view the grave stones of the men who boldly helped form our nation back in 1776. 

You may also get very confused like we did while trying to find the grave of Benjamin Franklin.  Although there is some signage related to Benjamin Franklin, he is not here.  He is at Christ Church’s other location a few blocks away. 

Of course, we didn’t make it over there until the day I went home, and the cemetery didn’t open until noon.  We had to miss this one too, but thankfully you can still easily view Ben Franklin’s grave right behind the fence. We did join the other visitors in throwing a penny on it for good luck. However, I just read that this practice is actually damaging the grave…

Ben Franklin grave site at Christ Church in Philadelphia

Grab a Snack

We stopped on over to Revolution House, a nearby eatery, and ordered some delicious drinks and buffalo dip.  It was a really cool spot actually, with a dark lit edgy feel.  There were old brick walls, the bathrooms were down the stairs in the basement, and soulful R&B played in the background. 

Hit Up a Brewery + Eat Cheesesteak

Over 2 days in Philadelphia, beer lovers must check out at least one brewery. There is a lot of craft beer brewed in Philadelphia, and to be honest, we barely scratched the surface. That’s probably because the sweltering heat had us looking for cocktails rather than heavy beers.

We still managed to pop into 2nd Story Brewing, and split two tasting paddles between the three of us (though my sister’s BF barely partook!).

After this we searched for a place to eat cheesesteaks because it’s Philly, and happened upon Sonny’s. I have to say, I bowed out of eating it with cheese wiz spread, which was probably a mistake. The meat was so bland and dry being topped with only provolone. I’m unsure if the sandwich was that unimpressive or if I just don’t like cheesesteak.

exterior of Sonny's cheesesteak restaurant - 2 days in Philadelphia
philly cheesesteak - 2 days in Philadelphia

It’s worth mentioning that this was not the most famous cheesesteak place in Philly. The most known are two historically dueling joints across the street from one another called Pat’s and Geno’s. However, my hubby tried both back to back and was so underwhelmed that he could not choose a favorite. That being said, every local will tell you their favorite cheesesteak place in Philly, and there will most likely not be a concensus among anyone you speak to.

2nd Night Out in Philadelphia

Saturday evening was when we went to my favorite spots of the whole trip. If you are in Philly during summer, and are looking for some awesome bars to check out, definitely consider Morgan’s Pier and Bok Bar.

Morgan’s Pier is located on the Delaware River, has a huge patio, and delivers awesome views of the Ben Franklin Bridge. We came here at the beginning of our night for appetizers and drinks, choosing to save the sunset for the next amazing spot…

view of Ben Franklin Bridge from Morgan's Pier

Bok Bar was the perfect place to arrive at in time for the sunset. This unsuspecting yet trendy joint was located on the rooftop of an old high school. Yep, you heard me right. It was super weird to enter the hall with lockers and all, especially having never been there before.

Once inside, you take an elevator to the top floor, which has a restaurant and the rooftop bar outside. What you get is sweeping views of downtown Philadelphia that you never knew existed. We got there at the perfect time, right before the sun set over the city. The ambience was incredible and definitely made the trip that much more memorable.

blonde and brunette girl at Bok Bar rooftop at sunset - 2 days in Philadelphia

One caveat – there were some Instagram models there doing a photo shoot, which was super weird and uncomfortable. Can’t guarantee this was a one time deal.

Clearly not much eating had actually taken place yet, but not to worry. After this gorgeous view, we couldn’t resist the urge to head to downtown Philly to hunt down sustenance. We landed at Iron Hill Brewery, where we shared some good bar snacks off the late night menu.


2 Days in Philadelphia: Departure Day

Rocky Statue

You can’t visit Philadelphia without seeing the Rocky Statue and taking a run (or walk) up the steps of the Philadelphia Museum of Art. I can’t even tell you how many people flex in front of that statue and then play the Rocky Theme song on their phone as they run up those steps. I did in fact walk up them, as I’m not a big enough Rocky fan to exert that much energy in the heat. There is a nice view of the city at the top though!

Rocky statue in Philadelphia - 2 days in Philadelphia
rocky stairrs at philadelphia museum of art

Sabrina’s for Brunch

Our last stop of my trip was this cozy little breakfast spot called Sabrina’s, which was packed to the brim when we arrived. Thankfully, it’s the kind of diner atmosphere that turns tables quickly, so the three of us were sitting in no time. The friendly waiters at Sabrina’s bring you your coffee in mismatched mugs that make you feel like you could be sipping it in the comfort of someone’s living room.

Their menu didn’t exactly specialize in lighter fare, but I was craving me some French toast anyhow. I was in luck, as they had some challah bread French toast on their menu that I was quite excited to see. My sister ordered chicken and waffles, which was also very tasty. Although I was ready for a nap after this, instead I had to head back to the airport and start my journey back to Cleveland.

• • •

And just like that my 2 days in Philadelphia were done, and I was right back home in The Land again. While living so far from my siblings can suck at times, it’s really sweet that I have the opportunity to explore new cities with them. Philadelphia was an amazing place to check out for brewery and history loving people. You should probably add it to your bucket list immediately if that sounds like something you’re into!

The best things to do during 2 days in Philadelphia, including awesome bars, restaurants, and historical sites in various unique neighborhoods. If you travel to Philadelphia, be sure to add this bar to your bucket list for a view of the skyline. Besides food like Philly Cheese Steaks, in Philadelphia you can find Ben Franklin Sites, Independence Hall, and the Rocky Steps.  This 2 day Philadelphia, PA itinerary will make sure you see the best of the top neighborhoods, like Old City.
The best things to do during 2 days in Philadelphia, including awesome bars, restaurants, and historical sites in various unique neighborhoods. If you travel to Philadelphia, be sure to add this bar to your bucket list for a view of the skyline. Besides food like Philly Cheese Steaks, in Philadelphia you can find Ben Franklin Sites, Independence Hall, and the Rocky Steps.  This 2 day Philadelphia, PA itinerary will make sure you see the best of the top neighborhoods, like Old City.
The best things to do during 2 days in Philadelphia, including awesome bars, restaurants, and historical sites in various unique neighborhoods.  If you travel to Philadelphia, be sure to add this bar to your bucket list for a view of the skyline... #philadelphia #philadelphiathingstodo #philadelphiarestaurants #philadelphiafood #philadelphiatravel #philadelphianeighborhoods #2daysinphiladelphia #philadelphiaitinerary
The best things to do during 2 days in Philadelphia, including awesome bars, restaurants, and historical sites in various unique neighborhoods. If you travel to Philadelphia, be sure to add this bar to your bucket list for a view of the skyline... #philadelphia #philadelphiathingstodo #philadelphiarestaurants #philadelphiafood #philadelphiatravel #philadelphianeighborhoods #2daysinphiladelphia #philadelphiaitinerary

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