Itinerary for the Best Weekend in Philadelphia

I am the Director of Marketing for Founding Footsteps Tours as well as the company’s resident millennial and first full time hire. I’ve lived in Philly for nearly ten years, and like most long-term residents, I absolutely adore it. When my Bostonian best friend (I try not to hold the Boston thing against her) told me she and her husband (who has never been to Philly) were planning on spending a long weekend in Philadelphia, I was so excited to set up this itinerary for the three of us. I like to think of it as a good balance between classic Philly and local best kept secrets.

Friday – Day 1

City Hall Tower Tour 

It’s the very first day and the best way to get acquainted with the city is from the top of Philly’s most iconic building, City Hall. The rickety elevator ride is just as charming as the panoramic views from 548 feet up. The waiting room before the ascent is full of interesting facts about the municipal behemoth (like that it’s the largest masonry building in the world and that it took them thirty years to build) and the elevator operator is always up for some light conversation. Even though there are tons of places in the city with a great view, there’s nothing quite like being right underneath William Penn’s feet. Fun bonus fact: This is where our founder proposed to his wife.

view of Philadelphia's skyscrapers from city hall

view of Philadelphia's skyscrapers from city hall

Reading Terminal Market for Lunch – 51 N. 12th Street

Reading Terminal Market is a fairly standard tourism spot, but it’s a classic for locals as well and once you go inside, it’s easy to see why this iconic Philadelphia landmark is so beloved. Opened in 1893, it’s one of America’s oldest and largest public markets and it currently houses over 80 different food vendors offering every type of cuisine you could possibly imagine. One of my absolute favorites?

DiNic’s Roast Pork sandwich with broccoli rabe and provolone – this could easily be split three ways and would leave some room for Beiler’s Doughnuts or a few cookies from 4th Street – heck, why not both? It’s vacation after all!

Beilers donuts in the Reading Terminal Market

Even Ben Franklin loves Beiler’s

Beilers donuts in the Reading Terminal Market

I didn’t have a “for scale” object, but this sandwich is HUGE

Using the Phlash to Get Around

For the first day, I mostly wanted to explore greater Center City and the museum district. I’ve found that taking the “tourist friendly public transportation” Phlash Bus is the easiest and most cost-effective way to do this. It stops at every major tourist attraction from Old City to Fairmount Park, and only costs $5 to ride all day. SEPTA key card holders (myself) ride for free. From May 1st – September 2nd, it runs every daily every 15 minutes from 10am till 6pm. My friends and I will hop on at stop #4, right outside of the Reading Terminal Market, on the corner of 12th and Market.

Eastern State Penitentiary – 2027 Fairmount Ave (stop #9 on the Phlash)

Eastern State Penitentiary is another classic tourist spot but definitely worth the visit. The museum, which is inside a once operational jail, offers really interesting details about the “Pennsylvania System” and the impact it has on modern day prison systems. You’ll get to explore most of the prison including the infirmary, “the hole”, and Al Capone’s lavish jail cell. The self-guided audio tour narrated by Steve Buscemi, abandoned castle like architecture, local artist instillations and the deep reflection on our modern-day prison system are absolutely worth the $14 admission fee.

one of the cell blocks in Eastern State Penitentiary in Philadelphia, PAThis is a view of one of the cell blocks inside the prison


Shofuso Japanese House and Garden – Lansdowne Dr & Horticultural Dr

(Hop off at Phlash at stop #12, and transfer to the Zoo/Please Touch museum loop. Exit at the Please Touch museum, the Shofuso house is about a three-minute walk)

The Shofuso Japanese House and Garden is one of Philadelphia’s best kept secrets. This traditional 17th century style Japanese house and garden was actually built in Japan and currently resides in Fairmount Park (the largest municipal park in the United States). The beautiful and tranquil environment makes it easy to forget there’s a bustling city less than a few miles away.

Shofuso Japanese House and Garden in PhiladelphiaPhoto Credit: Kyle Huff for PHLCVB

Dinner time! Standard Tap in Northern Liberties  – 901 N. 2nd Street

After the Shofuso House, we’ll hop back on the Phlash to City Hall (stop #15) and take the Market Frankford El (our east/west subway) eastbound towards Northern Liberties. Hop off at the Spring Garden station and it’s about a six-minute walk to our chosen dinner spot, Standard Tap. Their menu is constantly changing and they offer a wide selection of hearty dishes using seasonal ingredients and local produce. You can get anything from a burger, to a chicken pot pie, to a duck confit salad. Along with outstanding food, they have an impressive locally brewed beer list, outdoor seating and they support initiatives like Pennsylvania’s Buy Fresh Buy Local movement and urban agriculture from Greensgrow Farms. Not only does everything taste good, but it feels good too.

Despite the fact that it’s been a long day, it’s Friday, Friday and we’ve gotta get down on Friday! Might as well hit one more spot before calling it quits, so off to one of my favorite breweries…

Chicken pot pie and Korean BBQ sandwich on a squid ink bun

Love City Brewing – 1023 Hamilton St.

It’s about a twenty minute walk from our last stop, so unless you’re up for that, the easiest way to get here is via Uber.

Philadelphia rich brewing history is currently being matched by a vibrant brewing culture and tons and tons of breweries. With its’ friendly staff, delicious beer, and cool modern space, Love City is easily my favorite brewery. Their motto: “We’re about good people, good beer, and a good way to cap off the day. It doesn’t need to be more complicated than that.”

Love City Brewing in Philadelphia, Pennsylvania It looks so inviting…

Saturday – Day 2

Breakfast at Knead Bagels – 725 Walnut Street

I understand this is a bold statement, but I’d argue that Knead makes just about the best breakfast sandwich in the city. All of their eggs are free range and their house knead aioli is made of pure magic. It’s also right across the street from Washington Square Park so if there aren’t any tables available, you can enjoy your sandwich surrounded by nature and lots of hungry squirrels.

bacon egg and cheese sandwich from Knead in Philadelphia

Simple, but delicious. Bacon, egg and cheese on an everything bagel.

Wandering Around Old City

Knead is right on the cusp of Old City, which is a lovely area to explore. It’s called old city, creatively, because it’s the oldest part of the city. Philadelphia in general, and this area in particular, has tons of history to the point where it can be a bit overwhelming. My friends and I are going to take, what I call, the “history light” option, and stop by a few easily accessible and picturesque places.

  • Ben Franklin’s Grave (340 N 5th St) – We’ll even throw some pennies on his grave for good luck.
  • Elfreth’s Alley – The longest continually inhabited street in the original colonies. It’s great for pictures if you want that quintessential Philadelphia cobblestone shot.

Elfreth's Alley in Philadelphia, Pennsylvania

The cobblestone streets never lose their charm.

  • Shane’s Confectionary (110 Market St) – Open in 1863, Shane’s is the oldest candy store in the United States and their store, which still has the original 1860’s interior, truly feels like a blast from the past. Plus, the candy is to die for.
  • Christ Church (20 N. American St.) – For just $5, you can enter one of the oldest most historic churches in the United States also known as the Church of the Revolution. The church not only has tons of famous parishioners like Betsy Ross, Ben Franklin, George Washing and John Adams, but also friendly, knowledgeable and talkative docents that’ll tell you stories you can’t find in history books.

Christ Church tower in Philadelphia

This was the tallest building George Washington would see in his lifetime!

After all this, we’ll take a break from the history and do a little shopping and art gallery perusing. There are tons of adorable boutiques, non-cheesy souvenir shops and pop up art instillations worth exploring. All that wandering around will work up your appetite so it’s time for lunch…

Khyber Pass Pub – 56 S. 2nd Street

This tiny pub, tucked away in old city, specializes in Southern, Cajun and Creole cuisines, with 22 rotating craft drafts. Fun fact: the back bar was crafted by German woodworkers and used in the Centennial Celebration in 1876 prior to its use at Khyber Pass. The pubs old school coolness, delicious food and great beer selection make it the perfect place to take a mid-afternoon break.

Khyber Pass Pub in Philadelphia

I just love the old time feel of their brick facade

Edgar Allan Poe National Historic Site – 532 N. 7th Street (this is about 30-minute walk from Khyber Pass and is somewhat out of the way – taking Uber is your best bet)

Edgar Allan Poe lived in Philadelphia for six years and many people describe it as his most productive era. He lived in this home with his wife, Virginia and mother in law in 1843 before moving to New York City. While living here he wrote The Black Cat in which he describes a basement eerily similar to the one in his Philadelphia home. You have the opportunity to wonder around the house, check out the exhibits on his family, and chat with the park rangers who discuss the financial and emotional hardships he experienced while in Philadelphia. Not only will this chilling house put you in touch with Philly’s darker side, it’s also free!

Edgar Allan Poe House in Philadelphia

Photo Credit: K Huff for PHLCVB

Spruce Street Harbor Park – 301 S. Christopher Columbus Blvd (this is also over a 30-minute walk so again; your best bet is Uber)

If the Edgar Allan Poe house left you feeling (understandably) a little uneasy, Spruce Street Harbor Park will definitely cheer you up. This beautiful outdoor space is situated along the Delaware River and has all your summer needs – an abundance of colorful hammocks, gourmet food trucks, games for all ages, and tons of beer gardens. Luckily it isn’t just for beer lovers as they also sell frozen drinks in silly containers which is my personal favorite. We’ll sample tacos, burgers and soft pretzels from the food trucks and drink frozen drinks to our hearts delight. Depending on how nostalgic we’re feeling perhaps we’ll pay the $10 fee to paddle around on those silly swan boats (we’ll say we’re doing it for the gram, but really, we’re doing it for our childhood selves). Spruce Street Harbor Park is one of the best places to spend a few leisurely hours on a nice summer day.

Us, drinking frozen drinks to our hearts delight

Photo Credit: Matt Stanley

Founding Footsteps Beer and Band Tour – 239 Arch St.  (Fifteen-minute walk from Spruce Street Harbor Park)

Around 7pm, we’ll start heading towards the pickup location for our “Beer and Band” tour put on by my favorite local and family-owned tour company, Founding Footsteps. (Full disclosure – they do pay me but I’m not obligated to say that – although it doesn’t hurt) One of the company’s liveliest tours takes place on our BYOB trolley as live musicians entertaining you en route to visiting some of Philadelphia’s best beer gardens and breweries. You may get on the trolley as strangers, but after loudly (and poorly) singing along to “Don’t Stop Believing” and other bar favorites, you’ll leave as friends. The tour ends at 10pm at the Independence Beer Gardenwhich is a great place to have one final drink (or two).

One of our favorite musicians, John Gilbride!

Parks on Tap: Schuylkill Banks

Parks on Tap: FDR Park

Sunday (Funday) – Day 3

We’ve avoided the quintessential millennial “B” word up until this point… but hey, it wouldn’t be Sunday Funday if we didn’t do brunch.

Brunch at The Dutch – 1527 S. 4th Street

This place is a little out of the way, its technically in the Pennsport neighborhood but it’s worth the trek! It’s a breakfast and lunch spot only with cuisine inspired by the Pennsylvania Dutch, hence the name, The Dutch. They have the perfect mix of sweet and savory including Ana Banana Pancakes, and my personal favorite, an interesting twist on eggs Benedict where slices of ring bologna take the place of Canadian bacon and instead of hollandaise creamed chipped beef. Don’t come here on anything less than a completely empty stomach.

brunch at The Dutch in Philadelphia

A carafe of their specialty orange juice and a bottle of bubbles.

Pop up PHS Beer Garden – 1438 South St. (it’s about two miles away from brunch – Uber would be easiest)

The Pennsylvania Horticultural Society has a few of these pop-up beer gardens throughout the city, but the one on South Street is my favorite. The shabby chic ambiance and refreshing seasonal cocktails make this the perfect place to relax post brunch. Plus, all the proceeds help support the PHS mission to create healthier living environments and increase access to fresh food.

Photo Credit: Rob Cardillo

Magic Gardens – 1020 South St. (10 minute walk from the pop up beer garden)

The Magic Gardens, a two-block mosaic art environment created by artist Isaiah Zagar, is uniquely Philadelphia. The interactive museum hopes to inspire creativity and community engagement by educating the public about folk, mosaic, and visionary art. Its’ beauty inspires awe, and of course, a social media post or two.

After the Magic Gardens, this is a great opportunity to take in South Street. It’s one of the cities most vibrant streets and is currently home to vintage shops, bars, boutiques, music venues and restaurants. If you look closely you can still see remnants of its’ counter culture scene from the 60’s and punk vibes from the 80’s. It’s the focal point of the Orlon’s song “South Street”, which asks the question “Where do all the hippies meet?” and was referenced in the song “Punk Rock Girl” by The Dead Milkmen. Nearly forty years later, the street has held onto its funky scene and remains a great place for people watching.

Bok Bar – 800 Mifflin Street (It would be easiest to take Uber)

Keeping up with our South Philly theme of the day, our next spot is Bok Bar. This self-proclaimed “neighborhood bar giving you views of the neighborhood” resides at the top of an old school and easily offers one of the best views of the city. The idea that all of Philadelphia is one big neighborhood really resonates with me and feels like an ode to the sometimes gruff but overall wonderful attitude of the city. It’s easy to ponder this, and all the other reasons to love Philly while hundreds of feet above it, watching the sun set with loved ones. It would be the perfect end to the trip… but we have one more stop.

view of the Philadelphia skyline from Bok Bar in south Philadelphia

Absolutely breathtaking.

The Last Supper at Le Virtù – 1927 Passyunk Ave (10 minute walk from Bok Bar)

So by this point, we’ve ate and drank ourselves silly. But it’s the last night and I figured we could splurge a little at one of the Philadelphia’s nicer restaurants. The inspiration of this eatery is one of Italy’s wildest and most unspoiled regions, Abruzzo. They strive to serve the cuisine of the shepherds, farmers and fishermen, and man, is it delicious! The meats are house-butchered, the pasta is cut by hand, and the passion and love put into the food is obvious. These little details and the authenticity of it all makes for a truly remarkable dining experience.

After being so full of pasta that we can barely move, I’ll say goodbye to my friends (and readers – hi mom!), hoping that I’ve imparted a little bit of Philly love and appreciation.

4 hours
Group Size
Up to 36

South Jersey Brewery Tour

Visit three different local breweries on our BYOB trolley! Each stop is 30-45 minutes and your ticket includes either a pint or a 4-beer flight at each location. Light snacks are also provided on the trolley.

45 USD
3 hours
Group Size
Up to 36

Stand-Up & Drink

You drink, we drive! Take our BYOB trolley on a tour of the city while Philly's best comics keep you entertained along the way.

34 USD
2 hours 30 minutes
Group Size
Up to 36

Beer & Band Tour

A brewery tour of Philadelphia with live music on our BYOB trolley.

44 USD
1 hour 30 minutes
Group Size
Up to 36

Bad Things Happen In Philly

Hear chilling stories of the most heinous murders committed in Philadelphia. This BYOB tour is 21+ and contains graphic and disturbing content.

48 USD
Group Size
Up to 36

Private Events

All of our private tours are fully customizable.

Kick off your corporate event with a hilarious tour of Philadelphia on a trolley stocked with local foods and beers. Call on us to escort your bachelor or bachelorette party around the city while being entertained by live musicians or stand-up comedians. Have your wedding party arrive at the ceremony or reception in style on one of our historic trolleys.

1 hour 30 minutes
Group Size
Up to 20

Philly Phables Walking Tour

A Story-Telling Adventure! Trace the footsteps of our Founding Fathers in historic Old City with stories from the city's founding to the revolution. This tour brings history to life and makes you laugh!

22 USD
2 hours
Group Size
Up to 36

Historically Hilarious BYOB Tours of Philadelphia

An entertaining, comedic story-telling adventure through Philadelphia, covering the city's major attractions. Tours run an hour and 45 minutes. 21+ to drink.

25 USD
2 hours
Group Size
Up to 32

Holiday Light Tour - Private Party

Includes a live musician on the trolley, views of some of the best light displays in the city, a little bit of South Philly flavor. It will get even the biggest scrooge into the Holiday spirit!

1750 USD