Philadelphia is one of my favorite cities in the northeast. It’s a city full of American history, contagious nightlife energy, and delicious foodie stops that never disappoints me.
I just spent last weekend in the City of Brotherly Love, where I made it my mission to incorporate some (can’t believe I’m going to admit this) tourist attractions while revisiting favorite hangouts. As a young person who spent her college years a hop, skip, and away from Philadelphia, I’ve spent a lot of time exploring all that the city has to offer when it comes to entertainment and food. So I’ve made my own personal guide (with the help of GoPhila.com) to a weekend full of bars, Ben Franklin, and best places in Philadelphia to share with you all.

First tip I recommend is using a handy-dandy district map of Philadelphia (see above) to plan out your weekend. Being from New York, I gave no thought to walk everywhere. I was wrong. Though you CAN walk Philadelphia, I wouldn’t suggest walking everywhere. Pinpoint what you want to see, and what section it falls in so you know how much ground to cover if you do decide to walk. But don’t fret if you are scared to walk the distance, Philadelphia has great alternatives – public transportation anyone? Hop on a Septa bus for $2/ride or take the subway. Or just be lazy and cab it. That is another tip – try public transportation to get around as well.
Moving on. If you arrive on a Friday night and plan on checking out the night life, I suggest hitting up South Street, then Old City. South Street is the famous stretch that runs along the southern portion of Philly. It is conveniently located off I-95 so it is only a few minutes away, and has a vibrant locals scene. As one of the most popular areas of Philly, you’ll find lots of unique stores such as vintage thrift shops and collectors stores lined up, nestled between lively bars, neo-foodie restaurants, and classic dining spots. If you want a quick snack before beginning a night of partying, grab a heavenly slice from Lorenzo & Son’s Pizza, or go straight for the mouth-watering cheesesteak joint, Jim’s (hands down the BEST). Either way you will pay very little (money speaking, not healthy-wise) for a delicious result.

After satisfying your stomache, stop in for a first round of beers down the street at Jon’s. This is a low-key bar to go to with friends to catch the latest Phillies game and relax before making your way to the next hot spot…
…Which brings us to Old City! This is where the real fun starts. Full of buzzing crowds everywhere you go, Old City is home to a plethora of bars and clubs that welcome everybody – college kids, older couples, singles, and folks who just want to dance. Mingle your way through my favorites: Triumph Brewery, Plough & Stars, and National Mechanic to skip the lines, dress code, cover charges or any other entrance rule nonsense. Once inside, sip on inexpensive drink specials and drafts and most importantly, get your groove on!
Hopefully you enjoyed your Friday night barhopping through Old City. It is now time to wake up for brunch. Head on over to the Pink Rose Pastry Shop for some delicious and cheap home made breakfast classics. My friends and I ordered the works: eggs, potatoes, bacon, french toast, and biscuits which arrived shortly after – fresh and hot- ready to be devoured. Plus we sipped on bottomless coffee and nicely cold OJ which hit the spot. We even treated ourselves to some yummy treats like a giant macaroon and Phillies red velvet cupcake. To our pleasant surprise, the bill was under $30!

After your filling brunch at Pink Rose, it is time to get down to business and do some serious sight seeing. Walk through Society Hill up 3rd Street to Independence Hall to catch a glimpse of American History. Here you’ll stumble upon historical monuments and buildings such as the Ben Franklin House (which is really just a classy hotel now), the Liberty Bell, National Constitution Center, and of course Independence Hall – birthplace of American freedom and government. The best part about this section is that you get FREE historic walking tours! You can do this all on your own, without a tour guide, and pay nothing! Make sure you arrive before 5PM though, so as to beat closing time. All the monuments and buildings here are very welcoming to walk through, snap photos, and buff up on your history lessons too. There is plenty of security though, so be prepared for multiple bag checks. And of course, you are not the only one who wants in on our nation’s founding footprints, so expect to deal with lots of tourists too. We skipped all the long lines and hosted our own “express tours” by going straight to the Liberty Bell to snap some quick photos and learn the background of the Declaration of Independence at Independence Hall. Despite our rushed visit, it was great to learn some interesting, unknown facts about what really happened during the colonial days of America. Did I mention this was all FREE too?

Liberty Bell

Court Room replica

Signing of the Declaration of Independence
Now that you have refreshed your knowledge of American history, hit the parks! Follow Market Street west (up to you whether to walk, take a bus or subway) to check out my favorite architectural piece of Center City – City Hall. You cannot miss this giant beauty of a building, it intersects Broad Street and Market and is adorned in relief sculptures. Walk in through the middle of City Hall and you will notice an old (almost deteriorating) subway station in the far northwest corner, along with two odd abstract statues in the center. Admire the modern, yet Roman-eqsue construction that comprises City Hall then walk out towards the street to get a closeup view of its exterior. City Hall behind autumn trees is simply stunning.

Right across the street from City Hall is the LOVE Park, built by Edmund N. Bacon more than 30 years ago. The LOVE Park is populated by couples, tourists, and apparently skateboarders too. Take some photos of the famous fountain, but try not to jump in that tempting water – it’s against the rules! Then walk up to the park filled with giant game toy pieces and the wrestling statue for some fun photo opps. It is really hard to resist being playful and silly in this park, so soak it in!

Since you are in the heart of Center City, you can either mosey on down through Broad Street and take in the Arts district, or continue towards the Chestnut Street Shopping district. Broad Street (also known as Avenue of the Arts) is lined with theaters that house special events, performances, and operas as well as classy restaurants and lodging options. Since this is not my forte, I chose to do some quick shopping. Though this area is pricey, it makes for a nice stroll through in the afternoon. Hopefully you do not fall victim to an impulse purchase!
Considering it is now getting close to the evening, I recommend doing a nice dinner near Rittenhouse Square. I would highly suggest wining and dining (note: it is BYOB) at La Viola, an intimate Italian restaurant at South 16th and Spruce Street. It is quite small, and usually a wait, but the food is superb and surprisingly inexpensive. A “real deal meal” if you ask me. For an evening cap, take a relaxing walk through Rittenhouse Square, a Washington Square-type park for us New Yorkers.
That was a packed Saturday, eh?
Ending your stay in Philadelphia can be bitter sweet. But to make the most out of your Sunday, I would cab it over to the Philadelphia Museum of Art in the late morning to see the modern art exhibits at this beautiful gallery hall. Try attending on the first Sunday of the month where you pay what you wish, if not admission is $16 at most. I once was given a private tour of this museum and was absolutely taken aback at how gorgeous every piece of the building was, not to mention the art itself! If your tummy starts to grumble, grab an afternoon snack in their cafe in between your excursions. Once you are done impressing your friends (or date) with your art history, take an obligatory picture with Rocky outside.
Personally, my choice for a late lunch (or early dinner) on Sunday would be at Beneluxx, a low-lit romanticized bar and tasting room back in Old City. I fell in love with this cutesy lounge-space this past weekend as I sipped on a Stella and nibbled on a chef’s platter of foreign cheeses. Beneluxx is also a great spot for a first date. If you check this place out, I bet you will enjoy yourself here as well.

If you have a sweet tooth like me and would prefer indulging yourself with some dessert, then take a walk around the corner from Beneluxx to an old school ice cream parlor, Franklin Fountain. Here you will be overwhelmed by not only how cool this place is, but the array of frozen treats you can choose from. Franklin Fountain features a multitude of sundaes, shakes, banana splits, flavored sodas, and even classic candies too! We shared an appropriately named Mt. Vesuvius sundae which was dripping with chocolate fudge over brownie bits on a high bed of vanilla ice cream and sprinkled with malt dust. It was yummy! Franklin Fountain is great for people of all ages who love ice cream, no need to be ashamed here!

If you still are counting on a solid dinner to end your weekend, make your way across I-95 (you might want to try the bus or cab this time) to Penn’s Landing. Expect a more expensive, classier dining atmosphere though. One restaurant to look into is Moshulu, a sea-themed fine dining restaurant located right in the harbor. Their menu offers seafood and steak entrees, along with first course options. From the looks of it (since I’ve never been, but have always wanted to) the prices are pretty reasonable. Let me know how it is if you do eat here.
That is my ideal Sunday for a Philadelphia visit. A bit more relaxing, but still highly enjoyable.
Are you stuffed yet from all the food, walking, and entertainment this weekend in Philadelphia has shown you? Well, you should be! I hope the next time you think of a local weekend trip, you give the City of Brotherly Love a try.
If you have visited Philadelphia, I want to hear about it! Drop me a line below with your comments, or questions. If you want to see how I spent my weekend in Philadelphia, check out my trip on Sosauce here.
Read more posts by Alisha
Loved this. What a great itinerary of Philly and makes me want to go right now!
[...] down Washington, D.C. as the next place to revisit for my northeast adventures. Just like Philadelphia, I’ve been to D.C. several times but never experienced the true charm behind it due to [...]
I’m going to bookmark this post to use it next weekend! I live in Philly, but I need to check out some of these places you mentioned. Thanks!
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Wow thanks so much Caroline!
Whoa – I couldn’t have made a better itinerary myself. Great trip!