How To Make The Most of 36 Hours in Philly

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This year for Labor Day weekend, my good friend and I decided to travel to Philly. Something I loved about the trip was the fact that most of all the places we visited were walking distance.

The last time I was in Philly was years ago for a church summer camp and I can only recall visiting the Liberty Bell, walking the Rocky Steps, and eating a Philly cheesesteak. The touristy stuff. My friend Ryan and I created a Google doc of our long weekend trip and I kid you not, it’s thorough. 😂

My favorite thing about traveling with Ryan is how much we pack into our trips. We really do make the most of it. We’ll plan beforehand, make note of places we both want to see, explore, and eat at. And then we also mentally allow ourselves to be flexible with any sudden changes in our itinerary. Let’s be real: not everything will always go according to plan, and that’s perfectly okay.

In this travel guide, I’ll walk you through our 36 hours spent in Philly and everything we packed in. The itinerary allowed us to still have some downtime to relax and not rush through anything, so if you’re looking to visit Philly for a long or short weekend, I hope this is helpful!

DAY ONE:

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We took the NJ Transit from Penn Station to Hamilton. It was about an hour and a half train ride.. You can also take the NJ Transit to Trenton and then hop on the SEPTA train to 30th St. Station. Because we had the kittens, it was a better option for us to get an Uber from the Hamilton Station to our hotel.

view from the hotel room

view from the hotel room

We stayed at the Kimpton Hotel Monaco Philadelphia. The hotel was located in a prime spot — right beside Independence Mall overlooking Independence Hall and the Liberty Bell.

The hotel was also pet-friendly, a huge plus for anyone traveling with pets. The minute I let Pepper and Luna loose from their crate, they excitedly ran out and started to explore the hotel room. Their favorite spot was right here by the windows.

I also wanted to note that there were hand sanitizers in every elevator, ice room on our floor, lobby, and also by the exit. Masks were to be worn at all times in the lobby area, elevators, and other public areas. The hotel also had a restaurant / bar that was only serving outdoor dining. I felt safe with all of the safety protocols this hotel offered. Another huge plus.

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My outfit for day one — I had been itching to bust out my leather jacket and found this weekend to be the perfect excuse to wear it.

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Our first stop was Independence Hall, right outside our hotel.

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Next, we visited the grave site of where Ben Franklin was buried.

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Moving along the historical aspect of our trip, we visited the Betsy Ross House, which is the site where the seamstress and flag-maker Betsy Ross lived when she is said to have sewed the first American flag. The entrance fee was $5 per person and we had to wait in a socially-distanced line with limited capacity inside the house.

Something I remember from that visit: Betsy Ross faced many obstacles and challenges in her life which included deaths, tragedy, and kids. Reading about her life story in the House really put things in perspective. It was a good reminder that we really don’t know what people around us face and battle on an everyday basis, and to be more cognizant of that.

Here is an interesting fact about why the flag was on the floor.

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After the Betsy Ross House, we walked to Elfreth’s Alley, which was about a four-minute walk. This was definitely a place on our list that we wanted to visit. Again, want to note how much I love that Philly is a walkable city. A lot of the destinations in our itinerary were close by with short visits, which is why we were able to do as much as we did.

We made sure no one was close by and briefly took our masks off for a photo.

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I wanted to throw this sign in there because I was actually wondering if people lived in Elfreth’s Alley. It’s a touristy area, so I can’t imagine living in a place where there are people outside your window every single day.

From Elfreth’s Alley, we walked six minutes to Race Street Pier by the water.

Race Street Pier is a beautiful waterfront area with a lawn and bridge views overlooking the Delaware River where people can run alongside the bridge, eat food, and relax.

There were lots of places to eat and drink in the area but we decided to head back to the hotel to relax before our last stop of the night.

If you’ve been following me for awhile, you know how much I love a good view. And with a sunset? Cherry on top.We booked our tickets to One Liberty Observation Deck prior to the trip and decided to go right around 6:30-6:45 PM. That way, we could se…

If you’ve been following me for awhile, you know how much I love a good view. And with a sunset? Cherry on top.

We booked our tickets to One Liberty Observation Deck prior to the trip and decided to go right around 6:30-6:45 PM. That way, we could see the view of Philly in the daylight and also watch the sun set around 7 PM.

Sidenote: One Liberty Observation Deck just announced they have suspended operations indefinitely. 😥 This obviously happened a couple of weeks after our visit, but if you are able to visit in the future, I do highly recommend it.

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After the Observation Deck, we grabbed sushi on the way home. The first day was an exhausting one. We were both delirious and tired from the traveling and walking around in the sun. However, I wanted to try the Sweet Charlie’s rolled ice cream. Ryan told me it was a classic and something that was also on our list. Since I’m lactose intolerant, I went for the dairy-free birthday cake option. It had a unique taste to it, I will say. I’m not a huge ice cream person, but I’d definitely order it again!

DAY TWO:

On Sunday, we took a Lyft to Bud and Marilyn’s for brunch to meet one of his close friends. I was craving some biscuits and gravy and ordered the shaved ham biscuits + gravy on their brunch menu.

On Sunday, we took a Lyft to Bud and Marilyn’s for brunch to meet one of his close friends. I was craving some biscuits and gravy and ordered the shaved ham biscuits + gravy on their brunch menu.

If you squint hard enough, under the LOVE sculpture you can see the Rocky Steps in the background.

If you squint hard enough, under the LOVE sculpture you can see the Rocky Steps in the background.

The brunch spot was near City Hall, so we walked around the area before walking over to LOVE Park which was right across the street. LOVE Park is officially known as John F. Kennedy Plaza and is located in Center City, Philadelphia. This was another spot on our list because 1) it’s an iconic tourist attraction and 2) there’s another (and bigger!) version of this iconic sculpture in New York City and I had yet to see another one like it in person.


After doing some research, I found out that the artist Robert Indiana debuted the design as a painting in 1964 and then after constructing the aluminum piece, he lent it to the City of Philadelphia as part of the U.S. Bicentennial in 1976. The sculpture then moved for a short period of time to New York until it was bought and donated to Philadelphia again. It was restored, repainted, and reinstalled back in its original location.

There are other locations in the U.S. where you can find Robert Indiana’s LOVE sculpture. Have you visited one yet? Let me know where you’ve seen his work!

FUN FACT: Robert Indiana’s original LOVE sculpture is located in Newfields, the Indianapolis Museum of Art.

We walked to the Cathedral of Saints Peter and Paul, which is located on the east side of Logan Square.

FUN FACT: The Cathedral is the largest Catholic church in Pennsylvania.

When we walked in, it was so quiet to the point where you could literally hear a pin drop. What really caught my attention was the stunning interior. The marble-tiled floors, the intricate ceiling, the vaulted dome… it really was breathtaking.

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At this point, we were getting a bit hungry / thirsty for something refreshing, so we made a pit stop at Frutta Bowls for some smoothies. I ordered the Pink Flamingo — with pitaya, pineapple, mango, and almond milk. I think this was my first time trying pitaya in a smoothie… surprisingly good. He ordered the Whey Up — with vanilla whey protein, banana, strawberry, almond butter, and almond milk. Also tasty and refreshing.

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The AMOR sculpture — which is the Spanish-language version of the LOVE sculpture — is at Sister Cities Park, not too far of a walk from LOVE Park.

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I didn’t get a photo of Rittenhouse Square, but that was our next location. It’s a cute little park where you can relax, eat, drink, and socialize. It reminded me a lot like Bryant Park in New York City.

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Our next stop was University City — Drexel University and UPenn. Drexel University was on my list because it was my dad’s alma mater. I told him I would snap a photo on campus (see above for proof 😁).

Unfortunately due to COVID, we weren’t able to tour the main parts of the campus. 😥

UPenn was right across from Drexel University. Just like Drexel, a lot of the buildings on campus were locked and closed due to COVID. We were only able to access the outdoor areas. The campus itself is beautiful and the bricks remind me a lot like …

UPenn was right across from Drexel University. Just like Drexel, a lot of the buildings on campus were locked and closed due to COVID. We were only able to access the outdoor areas. The campus itself is beautiful and the bricks remind me a lot like UNC-Chapel Hill’s campus. I secretly enjoy walking on college campuses and every time I visit one, I try to visualize myself attending the college and what that lifestyle would be like.

Does anyone else do the same thing?

We didn’t have time to visit the 30th Street Station, but I was able to snap a photo of it while riding in an Uber.

We didn’t have time to visit the 30th Street Station, but I was able to snap a photo of it while riding in an Uber.

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Day two consisted of a lot of walking. After walking through Drexel and UPenn, we ended up exploring a rooftop park located on 80 S 30th Street. From a distance, we could make out a large tv screen showing the U.S. Open and people hanging out against a giant glass screen that overlooked the Schuyllkill river in the University City neighborhood. This was enough for us to be a little flexible with our itinerary and check it out.

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The public rooftop park is called Cira Green. It’s located on the 11th floor atop a parking garage.

There is also a rooftop bar and burger shack called Sunset Social. The place had music, tables, seats, and public restrooms. Definitely a good spot if you’re looking to hang out and enjoy the city views.

Location: 401 S. Christopher Columbus Boulevard

Location: 401 S. Christopher Columbus Boulevard

We got back to the hotel, washed up and changed for dinner.

Dinner was a surprise spot by the water on a beautiful ship called Moshulu. The ship is docked permanently at Penn’s Landing on the Delaware River Waterfront, and is known as the world’s oldest and largest four-masted tall ship.

FUN FACT: Moshulu is a Seneca Indian name that means fearless.

It’s not every so often you get to dine on a beautiful ship with a view of the Philadelphia skyline at sunset. The food was delicious — we both ordered the Crispy Skin Atlantic Salmon with tri-color quinoa, pickled cucumbers, and madras curry aioli. One of the best meals ever. And then we ordered a pitcher of red sangria to enjoy by the water.

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After dinner, we walked alongside the waterfront to see what was going on in the area.

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We ended up walking through the Bright Lights, Our City, a brand new light installation at Spruce Street Harbor Park.


There are rules you must abide by while walking through Spruce Street Harbor Park:

  • Visitors will be required to wear masks unless they are eating or drinking.

  • All forms of payment will be accepted at on-site vendors.

  • Food and beverage lines will be limited to 10 persons at a time.

  • Sanitizing stations will be available throughout the park.

  • There will be no hammocks.

  • Special signage and ground graphics will be posted to help visitors practice physical distancing. 

  • Bathrooms are open to the public and sanitized hourly.

We ended up walking all the way back to our hotel, which wasn’t too far of a walk.

Here is a shot of Luna “watching” the U.S. Open in the hotel room. You’re welcome.

DAY THREE:

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Day three was our last day in Philly. Even though we could’ve technically visited the Rocky Steps on day two, I wanted to space it out and also get a morning “workout” in before we left. In the shot above, you can see City Hall in the distance.

The Rocky Steps were a bit crowded with runners getting in their morning workout, tourists snapping photos, homeless people walking around inserting themselves into conversations to sneakily get some $$, and kids running up and down the steps.

Packed as any normal touristy spot would be.

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A sweet homeless guy offered to take a photo of us. Even though he messed up the angle and you can’t see City Hall 🤪, this shot is still one of my favorites.

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After the Rocky Steps, we Ubered to a brunch spot called Cafe Lift. Outdoor dining was full, so we ordered our food and ended up eating on the sidewalk right outside the restaurant.

I ordered their coconut ginger matcha latte — for those of you who like matcha… it was really good. 10/10 recommend.

We got back to the hotel, packed up our things, and headed back home to New York City.

Looking back at it now, that was a long weekend, but also a really fun and adventurous one. We really did make the most of it and I can wholeheartedly say that I will definitely be back to Philly in the near future.

I hope this travel guide was helpful! Let me know if you’re planning to visit Philly or if you’ve been to any of these places. And as always, feel free to reach out to me or leave a comment if you have any questions!

Thanks for reading!

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