How to have the ultimate weekend in Philadelphia

Philadelphia is a wildly different town to different people. The City of Brotherly Love is where the Founding Fathers invented modern democracy. Edgar Allen Poe lived here, and so did Will Smith. There’s a sizable Chinatown, an old Italian neighborhood and a long-thriving LGBTIQ+ community. There are 32 colleges, many of them world-class, and the city is a nexus of hip-hop, street art and more than 100 craft breweries.

Even to me, Philadelphia is many cities at once. I used to hit up the nightlife in my reckless youth; I married a Philly girl; and now we return to the city, again and again, to discover monuments and museums with our son. The city is gritty and gorgeous, colonial and cutting-edge, a study in contrasts.

So, how do you navigate this dynamic city of 1.5 million people, let alone with just a weekend? Hold onto your Phillies cap, because here’s the game plan.

• When to arrive: If you’re traveling light, action-packed Philadelphia is an easy place to kill time as you wait for your hotel room to be available. But most travelers will want to arrive in the late morning on Friday.

• How to get from the airport: SEPTA’s Regional Rail system connects every terminal of Philadelphia International Airport to the inner city. You can catch a train every 30 minutes on weekdays and every hour on weekends, and the trip into town takes 25 minutes.

• Getting around town: Urban Philadelphia is easy to navigate on foot, thanks to ordered blocks and level sidewalks. You can scoot to any neighborhood on the SEPTA metro system, a dynamic network of subways, elevated trains and even a trolley line. Driving a car is feasible, but using ride-shares will spare you a lot of downtown gridlock.

• Where to stay: The best accommodations in Philadelphia encircle the downtown area, known to all as “Center City,” and the closer you stay to City Hall, the better. A luxurious option is the Franklin on Rittenhouse, a historic boutique hotel with updated rooms and a sophisticated lounge. (My sister-in-law was married there, and the place surpassed her high expectations). Near the river, a former shipping warehouse from 1828 is now the stately Penn’s View Hotel; exposed brick walls and the Panorama Wine Bar make for a romantic getaway. Finally, backpackers will love Apple Hostels, a clean and cozy crash pad in the middle of the Old City District.

• What to pack: There’s no need to dress up in Philly, though you certainly can. Sensible shoes and an evening outfit are always a good idea. Also, remember to pack for inclement weather – Eastern Pennsylvania gets plenty of rain.

Friday

Morning: Kick off your weekend at Reading Terminal Market, a former train station-turned-dining hall. The place is packed with eateries, gift shops and vintage-style signs, and it puts you right in the middle of Center City. Walk a couple of blocks and spot City Hall, a gorgeous French-style building with a 548ft clock tower – the tallest structure in the world without steel supports.

How to spend the day: Most first-timers beeline to the Liberty Bell, Philadelphia’s most acclaimed monument. Each visit, I marvel at its size: a lower circumference of 12ft and a total weight of 2080lbs. The famous crack in its bronze cloche looks too perfect to be real. The Liberty Bell hangs in a voluminous glass enclosure in front of Independence Hall, where it was first rung after the signing of the Declaration of Independence. The Liberty Bell Center is free to visit.

This section of Philly is packed with historic attractions. Head to the African American Museum, a multimedia celebration of the city’s vibrant Black community, from civil rights activists to artists and statesmen. Then, visit the Betsy Ross House, where the legendary seamstress is said to have pieced together the first American flag. Want to ask her about it? A bonneted historic interpreter is ready for your questions.

After a healthy walk down Arch St, you’re basically required to snap a photo in JFK Plaza, better known as “Love Park,” thanks to Robert Indiana’s iconic pop-art sculpture of the word “Love” with the “O” askew.

Dinner: Philly’s funkiest section is South St, a gauntlet of bars, restaurants and novelty shops. Follow the colorful brick facades until you find a menu that fits your mood. There’s a little bit of everything here, from brunch spots to international fusion, but for local flavor, I recommend Tattooed Mom, the graffiti-covered diner-slash-bar. The Nashville Hot Chicken Sandwich is a favorite, and the many vegetarian options will go down nicely with a “Mom’s Mule” cocktail.

After dark: Broad St intersects with City Hall, and it’s packed with cultural institutions: the Miller Theater, the Wilma Theater, the Academy of Music and the Philadelphia Orchestra, among others. Nicknamed the “Avenue of the Arts,” Broad St is where Philadelphia’s finest performing artists showcase their skills, and you can expect a symphony performance or stage play to take place any night of the year.

Saturday

Morning: Head over to the South 9th Street Italian Market, a lively row of butchers and grocers that looks unchanged since the early 1900s. This is a great place to grab breakfast and people-watch. Or you can follow your stomach down to Passyunk Ave, a long corridor of restaurants, cafes and bars. Passyunk’s most famous landmarks are Geno’s Steaks and Pat’s King of Steaks, two retro-style cheesesteak joints that stand directly across from each other; they have long competed over customers at the intersection of Passyunk and S 9th St, so choose your loyalties wisely.

How to spend the day: This part of Philly is home to two eccentric museums: the Mummers Museum commemorates the colorful clowns who march through Center City in every New Year’s Day parade; the tradition dates back to 1901, and mummer brigades are serious business in Philadelphia.

If you have a strong stomach, you may dare to enter the Mütter Museum, a macabre collection of medical curiosities. Operated by the College of Physicians at Philadelphia, the Mütter Museum boldly displays organs and skeletons, many with startling features. Come prepared; patrons have fainted in here.

Dinner: The jewel of the Old City is Penn's Landing, a pedestrian waterfront packed with food trucks, a marina and the Independence Blue Cross RiverRink. A little farther down is Spruce Street Harbor Park, where summertime visitors can relax in public hammocks.

There are countless places to grab dinner along the Delaware River, but a worthy splurge is the Moshulu, a fine-dining restaurant housed in the hold of a four-masted tall ship. From the top deck, you can watch sunsets over the Delaware River, and during holiday fireworks displays, there’s no better view in the city.

After dark: Philadelphia is a sports town, to put it mildly, and the city has gathered all of its pro sports complexes in one area: the Lincoln Financial Field, Citizens Bank Park and Wells Fargo Center all stand within fly-ball distance of each other, directly south of Center City. Whatever the season, there’s a good chance the Phillies, Eagles, Flyers or 76ers are playing a home game, and the city gets wild.

A quirkier alternative is Philly by Night, a nocturnal tour of the city that cruises around in a double-decker bus. Knowledgeable guides recount historic anecdotes on this 90-minute ride, and you’ll likely spot a good place for a nightcap.

Sunday

Morning: If you haven’t already, consider a morning spin around town on an Indego Bike. The local bike-share program launched in 2015 and has attracted thousands of local and visiting riders. Download the app and pick from several traditional and pedal-assist models. Explore narrow Old City streets, where traffic is fairly light on Sundays, and many surfaces are paved with brick. Take Spruce St across Christopher Columbus Blvd, where you'll find the Delaware River Bike Trail – 2 miles of car-free riding along the waterfront.

How to spend the day: Save the best for last: a visit to the Philadelphia Art Museum. Yes, this institution is renowned for its collection of fine art – including paintings by Picasso and Rubens – but the museum’s most famous component is its staircase, which Sylvester Stallone dramatically ascended in the 1976 film Rocky. There’s a statue of boxer Rocky Balboa at the top, and yes, a snapshot is required.

Another iconic place to visit is the Eastern State Penitentiary, a fortress-like prison where a total of 75,000 people served time between 1829 and 1970. This controversial institution pioneered solitary confinement, and guided tours are now held in the haunting old cell blocks.

Your time is up, but there’s always more to see (and eat), so do come back. If home is far away, take the SEPTA train back to the airport. Alternatively, consider a trip to 30th Street Station, not far from the Art Museum. This stately old terminal is a busy hub for train travelers, and Amtrak connects Philly to cities up and down the East Coast.