When my boyfriend and I were planning his holiday stateside visit, we wanted to visit a new city together for New Year’s Eve.
We got the idea for Philadelphia during my birthday visit to Paris in early November. He was watching a few Rocky films and voilà…
It seemed fitting to start the New Year in a place that neither my boyfriend nor I have ever visited. There was something novel for both of us and we had no idea what to expect.
Here’s a quick guide on how to spend a winter weekend in Philadelphia, Pennsylvania:
- Where We Stayed | The Cutest Airbnb in Philly
- What to See & Do in Downtown Philadelphia
- Where to Eat in Downtown Philadelphia
- BYOB in Philadelphia

Where We Stayed | The Cutest Airbnb in Philly
We found an Airbnb at a restored colonial carriage house in Northern Philadelphia. It was a drive away from the city center, but all of the reviews raved about what a “hidden gem” the property is.
Although there are no pictures of the interior, the grounds of the carriage house and the main house are quite stunning. The estate sits up high on a hill away from the surrounding blocks of attached homes—it’s the perfect place for a quiet getaway at the end of a long day walking (and eating and drinking) around Philadelphia.
Note: We did drive to Philadelphia from Connecticut, but we ended up ordering Ubers everywhere. An Uber Pool rarely cost over $12, averaged $8-$10.


What to See & Do in Downtown Philadelphia
Downtown Philadelphia is easy to walk around. With that being said, it’s a bit bigger than you may think.
It takes 30 minutes to walk from the Liberty Bell and Independence Hall in Old City to the more upscale shopping and dining district around Rittenhouse Square. To reach the Philadelphia Museum of Art from Rittenhouse Square, it also takes another 30 minutes walking.
We probably would have walked more if it wasn’t for the cold, rainy weather that we had. I should have also been more practical and worn sneakers instead of high-heeled leather boots…

Independence Hall
Independence Hall, which is run by the U.S. National Park Service, was closed because of the federal government shutdown at the time of writing. There was a long but civil queue to catch a glimpse of the original Liberty Bell from one of the museum’s windows.

Walking around Philadelphia opened my eyes to another side of the American spirit. A certain friendliness, a work ethic, an eclecticism, and grit that I hadn’t yet encountered and that is so removed from the electric current in New York or sports fanaticism in Boston.

Elfreth’s Alley
This historic street is like the Philadelphia version of rue Crémieux in Paris, France (or aesthetically, at least). The storybook brownstones make up the oldest residential neighborhood in the United States in Elfreth’s Alley and remain owner-occupied to this day.








Philadelphia Museum of Art
When I saw that the Philadelphia Museum of Art was holding an exhibition on Dior’s New Look and Beyond, I couldn’t have purchased the tickets fast enough. My boyfriend’s main priority was to get a “victory” photo on the steps of the museum like Rocky Balboa, so we were both pleased in the end.
Fact: The admission ticket to the Philadelphia Museum of Art allows you to visit over two consecutive days. Book your tickets in advance and preview the current exhibitions on the museum’s website.




And it goes without saying that we looked for the European art collections…
And of course, we had a great preference for French artists…




Mummers Parade (New Year’s Day only)
If you’re lucky enough to be in Philadelphia on New Year’s Day, you must see the Mummers Parade. We didn’t have any idea about the parade when we came into town, but it’s a 120-year-old tradition that is unique to Philadelphia.
Basically, thousands of costumed performers play music, sing, and dance from City Hall all the way down Broad Street for the entire day. Each troupe is judged to determine the best group performances.
We didn’t play for tickets to see the performances from the bleachers by City Hall. However, we were able to watch some incredible group routines rehearsing in the northwest direction of City Hall. It was so much fun to see the wild costumes, set design and, props throughout the parade.

Where to Eat in Downtown Philadelphia
The restaurant scene in Philadelphia is centered around local neighborhood joints that serve both American comfort food and healthy options with fresh ingredients. Each restaurant had their own personal ambiance and color that welcomed everyone who walked through the door—we didn’t feel pressured to follow a certain decorum to fit in.
Luna Café on Market Street
Luna Cafe was one of the cute brunch options in town. If we had stayed in Philadelphia for another day, I would have wanted to come back here again to try another plate.

High Street Bakery
Located across the street from Luna Café, you can already taste the fresh bread when you open the front door.

City Tavern
If you’re looking to take a break while walking around Old City, stop into City Tavern, the historic watering hole for the Founding Fathers in Philadelphia.
Do the beer tasting flight and you’ll sip the original recipe for Thomas Jefferson’s go-to ale or George Washington’s porter using the recipe uncovered from the Rare Manuscripts Room of the New York Public Library.
Experience American history one beer at a time…

a. kitchen and a. bar
a. kitchen is the restaurant we chose for New Year’s Eve dinner. The French-American restaurant offered a wine pairing with the prix fixe menu, so it seemed to be the best choice for us.
We were impressed with the plate presentation, freshness of ingredients, and the level of service. I was very pleased with my wine pairings for all three of my courses.
After dinner, we had a nightcap at a. bar around the corner.


Pat’s King of Steaks
And of course, we did eat Philly cheesesteaks at Pat’s King of Steaks. There are a ton of places in Philadelphia to find the signature sandwich, but Pat’s was the most recommended to us by friends and family.
Also, it was featured in Rocky—we had to stay consistent with our theme!

BYOB in Philadelphia
Another fact about Philadelphia—when a restaurant says that they are BYOB, they aren’t kidding. They don’t serve alcohol period, so you need to actually bring your own bottles.
In my experience, restaurants in Rhode Island or Connecticut that are BYOB do still offer a limited selection of wine or beer. It was a surprise when we were told at La Viola that we needed to find our own wine.
To the restaurant staff’s credit, they were very nice to suggest a local liquor shop down the street—unfortunately, it closed early for New Year’s Day.
Thankfully, we had noticed that the wine bar we had been at earlier in the evening did sell bottles of wine to go, so my boyfriend went back to Tria to select the right wine. In the end, we were successful.
“A wine-less meal is a worthless meal”

As we drove away from Philadelphia and made our way back to New England, we kept saying how we were pleasantly surprised by the City of Brotherly Love. There’s so much allure to international travel as an American, but it goes to show that you can see and learn so much by simply opening your eyes to a new part of your own backyard.


I love the photos of everything all decorated!! It’s a shame you couldn’t actually go in to see the Liberty Bell.
I haven’t been to Philly since I was young and never did any of the tourist things. We would just go to see my Dad’s cousins who live there, not in the nicest area, haha! But I’d love to go around christmas to see the streets like you have shown.
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Thanks, Meg! I would recommend checking out Philly now, even for a quick weekend. Maybe I’ll go back again to see the Liberty Bell and the other attractions that were closed during my stay.
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I imagine it’s hard not to fall for those charming old brownstones! I’ve never visited Philadelphia, but I’m so close, clearly I’m missing out!
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Yes! If you’re close by, take a day trip 🙂
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Oh wow! This looks like a spectacular trip! I really want to go to Philly and this just confirmed it for me. So many quaint and historic nooks and crannies!
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“Historic nooks and crannies” summarizes downtown Philadelphia perfectly! Thank you for taking the time to read 🙂
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These pics are stunning! I love Old City Philly
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Thank you so much!
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I have actually never been to Philadelphia but now I want to go!!!
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You definitely should!
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I’ve only been to Philly for work but I’ve been dying to go for a pleasure trip && these look like all great suggestions of things to do’
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Oh that’s it! I’m sold! Taking a trip this year!
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