The Unexpected Philadelphia Itinerary

Go off the beaten path to find hidden gems: some fascinating, some extraordinary, and all unexpected. Philadelphia is known for its history and American tradition, but it’s also home to many sites and attractions that are anything but traditional.

Day 1

Morning

Start in Old City and grab a coffee from The Bourse. Once the nation’s first commodities exchange, the historic building is now home to a modern food hall with 20+ vendors. Afterwards, take a short walk to nearby Christ Church and sit in the pews where the nation’s Founders once worshipped. Pay your respects to Ben Franklin at the church’s nearby burial grounds.

Staying in the historic district, visit the National Liberty Museum to examine the principles of freedom and liberty. The museum features include the 21-ft Flame of Liberty by renowned glass sculptor Dale Chihuly and a crack-less, ring-able copy of the Liberty Bell.

Afternoon

Head to the Delaware River Waterfront and explore Cherry Street Pier. This former municipal pier is now a mixed-use space with artist studios, rotating exhibitions, and pop-up events. Enjoy lunch at The Garden at Cherry Street Pier, a seasonal, open-air dining area that offers stunning views of the Delaware River and Benjamin Franklin Bridge.

Or journey to South Street, where you can bask in the reflections of Philadelphia’s Magic Gardens. Half indoor, half outdoor, fully out of the ordinary, this mesmerizing folk-art labyrinth is the largest work to date by mosaic artist Isaiah Zagar. Explore the surrounding streets as well, to see where Zagar’s unique mosaics have “spilled out” into the surrounding neighborhood.

Evening

For dinner, enjoy traditional Italian dishes and an extensive wine list at Victor Café. This cozy South Philadelphia restaurant that was featured in several Rocky and Creed films. Here, the servers double as professional opera singers who perform every 20 minutes.

Walk off your meal by chasing the sunset along the Benjamin Franklin Bridge’s pedestrian walkway. Enter at 5th & Race streets and head east to encounter one of the best views of the city as you hover over the Delaware River. End the day in Old City with a candlelit Ghost Tour. The tour will reveal the more macabre past of Philadelphia’s historic haunts, including Washington Square and Independence Hall.

Day 2

Morning

Start the day on the University of Pennsylvania campus. Embrace your inner Indiana Jones and unearth an amazing collection of artifacts at the Penn Museum — including the largest Sphinx in the western hemisphere.

Then, take a short walk to Cira Green, a picnic-perfect park in the sky with amazing views of Philadelphia’s skyline. Grab coffee and snacks to-go from the nearby Walnut Street Café and enjoy them while atop Cira Green.

Afternoon

Cross the Schuylkill River and visit the Mütter Museum – named one of Lonely Planet’s “unique museums around the world you can’t miss.” The Mütter’s unique exhibits and specimens tell the story of medicine through the lives of individuals, the conditions they faced, and the tools and therapies used to treat them. A visit to the Mütter is a fascinating journey through scientific history.

Then, make your way to North Philadelphia for the free-to-visit Wagner Free Institute of Science. The museum houses over 100,000 specimens, including fossils, shells, skeletons, and skins displayed in original wood and glass cabinets.

Beloved gastropubs and hip brunch spots abound in Northern Liberties. After enjoying lunch, shop your way through the neighborhood’s collection of independent boutiques. Nearby, peer into the study of the Edgar Allan Poe House, where one of America’s most influential writers penned some of his well-known spine-tinglers.

Evening

End the day with dinner and a show in Philly’s vibrant Fishtown neighborhood. Attend a concert at a local venue like the Fillmore or Johnny Brenda’s. Or visit Fabrika, a local dinner theatre featuring circus-style acts and burlesque performances.

Day 3

Morning

Wake up and take a bite of scrapple — an authentic Philadelphia breakfast delicacy — at Down Home Diner in Reading Terminal Market. Or savor other early morning eats from one of the other 25+ eateries. Take a short walk north to explore The Rail Park – an elevated park occupying former train tracks of the Reading Railroad (of Monopoly fame). Relax on an industrial swing before exploring the murals nearby.

Afternoon

Drink up and explore one (or several) of Philadelphia’s local breweries and beer gardens. Don’t miss Yards, Philadelphia’s original craft brewery, with recipes inspired by the Founding Fathers. Sign up for a guided tour offered by City Brew Tours to travel from brewery to brewery (via a designated driver), sampling local suds and learning more about the brewing process along the way.

Pass through East Fairmount Park and explore Laurel Hill Cemetery – a 78-acre National Historic Landmark and the nation’s second oldest cemetery. Explore with themed tours including art and architecture; pop culture and contemporary stories; and lore and legend. Or schedule your own ghost hunt with a Private Ghost Hunting Planning Guide.

Change course toward South Philadelphia and explore one of the world’s greatest collections of racing sports cars at the Simeone Foundation Museum. Visit on Saturdays to see these vintage vehicles rev their engines and burn rubber in the parking lot. Take a lap around the lake in the middle of FDR Park, South Philadelphia’s largest park. Along the way, visit a romantic pavilion, an iconic skatepark, and the American Swedish Historical Museum — the oldest Swedish museum in the United States.

Evening

No matter the time of year, East Passyunk Avenue is often home to the newest it-restaurant. If you’re craving Italian for dinner, there’s no better locale, but don’t miss the other international eateries that line the thoroughfare.

Cap your unexpected Philadelphia experience by raising a glass against the beautiful Philadelphia skyline while on top of a former South Philadelphia school. Bok Bar tops what is now a mixed-use space filled with artist studios and other small businesses. On the south side of the roof is Irwin’s, an Italian restaurant with indoor and outdoor seating (and even more views).