Philadelphia is the scrappy, underdog brother of New York City—grittier, cheaper, and with a significantly bigger chip on its shoulder. It is a city of row homes and cobblestones, where the Declaration of Independence was signed just blocks away from where locals scream profanities at football games. The air smells of soft pretzels, frying onions, and history. It is America’s first World Heritage City, but it refuses to be a museum piece.
The attitude here is legendary (“Philly vs Everybody”). People are blunt, loud, and fiercely loyal. But beneath the tough exterior is a city of neighborhoods with deep community roots. Passyunk Avenue is a culinary explosion, Fishtown is the hipster capital, and the Gayborhood is vibrant and welcoming. The food scene is arguably the most underrated in the country—yes, there are cheesesteaks (please don’t go to Pat’s or Geno’s), but also world-class Israeli food, BYOB bistros, and the chaotic glory of Reading Terminal Market.
Philly is walkable and human-scale. You can see the crack in the Liberty Bell and the Rocky Statue in the same afternoon. The mural arts program has painted the city in color, turning blank walls into storytelling canvases. It feels lived-in, honest, and unpretentious.
Don’t look for polish here. Look for character. Eat a roast pork sandwich with broccoli rabe, drink a “Citywide Special” (beer and a shot) at a dive bar, and trust the process.
The perfect plan for Philadelphia:
Day 1 Agenda
Theme: Liberty & Roast Pork
- Morning: Old City. See Independence Hall (Book tickets in advance). Peek at the Liberty Bell through the glass (don’t wait in the long line just to see it closer). Walk Elfreth’s Alley (oldest street).
- Afternoon: Reading Terminal Market. Sensory overload. Skip the tourist cheesesteaks. Go to DiNic’s and get the Roast Pork with Broccoli Rabe and Sharp Provolone. This is the real Philly sandwich.
- Evening: Gayborhood/Midtown. Dinner at Vedge (vegetables that taste like magic) or Double Knot.
Day 2 Agenda
Theme: Art & Rocky
- Morning: Philadelphia Museum of Art. Run up the “Rocky Steps.” Take the photo. Then actually go inside—the collection is massive.
- Afternoon: Eastern State Penitentiary. A haunting, ruined prison where Al Capone was held. The audio tour (Steve Buscemi) is incredible.
- Evening: Fishtown. The cool neighborhood. Pizza at Pizzeria Beddia (world class). Drinks at Frankford Hall or a dive bar like Johnny Brenda’s.
Day 3 Agenda
Theme: Magic & Markets
- Morning: Philadelphia’s Magic Gardens. A mosaic labyrinth on South Street made of trash and tiles. Totally unique.
- Afternoon: Italian Market. Walk 9th Street. It looks like the 1970s. Buy cheese at Di Bruno Bros. Grab a taco at South Philly Barbacoa (famous from Chef’s Table).
- Evening: Passyunk Avenue. The restaurant row. Dinner at Laurel or Barcelona Wine Bar. Finish with the fountain view at the Singing Fountain.
Weather
Spring (April-May): Cherry blossoms in Fairmount Park. Mild. 60-70°F.
Summer (June-Aug): Hot, humid, sticky. locals flee to “The Shore” (Jersey beaches).
Autumn (Sept-Nov): Best time. Crisp air. Sports season (Eagles) energy is insane.
Winter (Dec-Feb): Cold, gray, potential snow.
Local Customs
1. Ordering a Cheesesteak: “Whiz With.” That means Cheez Whiz and onions. Have your cash ready. Do not hold up the line.
2. Sports: Do not wear a Cowboys, Giants, or Mets jersey unless you want trouble. Seriously. Eagles fans are intense.
3. BYOB: Many best restaurants are Bring Your Own Bottle (wine/beer). Check before you go.
History & Culture
Founded by William Penn in 1682 as a “Holy Experiment” of tolerance, Philly became the heart of the American Revolution. It was the US capital before DC. Benjamin Franklin walked these streets. It became an industrial powerhouse (“Workshop of the World”), declined in the late 20th century, and has roared back as an ed & meds hub.
Getting Around & Safety
SEPTA: The subway (Broad St Line / Market-Frankford) is gritty but gets you there. Buses are frequent.
Walking: Center City is extremely walkable.
Indego Bikes: Blue bike share stations are everywhere.
Info for Nomads
Affordable and cool. Great coffee shop culture. Close to NYC (1.5 hrs train) for meetings.
Workation Vibe
Speed: 300 Mbps+ (Comcast HQ is here).
Cafes: Elixr Coffee (Center City) – dark, woodsy, award-winning roast. Reanimator Coffee (Fishtown) – Local favorite.
Frequently Asked Questions
Pat's or Geno's? +
Neither. They are tourist traps. Go to Angelo’s Pizzeria (South Philly) or John’s Roast Pork. Better meat, better bread, no neon lights.
Is it safe? +
Center City and Old City are safe. Parts of North and West Philly can be dangerous. Stay in the main tourist/restaurant zones and use common sense.
What is a Wawa? +
It’s a convenience store. But it’s a lifestyle. Go there, order a hoagie on the touch screen, get a coffee. It is the fuel of Philadelphia.