Philly Cheesesteaks and City Charm: A 3-Day Weekend Guide

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Advisor - Ashlyn Terry
Curated By

Ashlyn Terry

  • Arts & Culture

  • City Travel

  • Food & Wine

  • Philadelphia

  • Local Culture

  • Local Food

  • Entertainment

Travel advisor Ashlyn standing in front of the red PHILLY sign in the middle of the city with a fountain behind
Curator’s statement

Philadelphia's energy is infectious! It's no wonder I have made it a point to visit three times in the last few years. From vibrant history to trendy eats, this city offers something for everyone. This itinerary combines iconic landmarks with hidden gems, all within easy reach. Get ready to fall in love with Philly's unique character in this two-day Philly escape, with an optional NYC getaway!

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Day 1: Fueling Up & Feeling the Soul

A serving of French toast with banana slices and syrup on a white plate
  • Brunch at Sabrina's Cafe: Start your day with delicious soul food at Sabrina's. Their portions are generous, so come hungry! Insider Tip: Try their stuffed brioche french toast – you won't regret it!

  • African American Museum: Immerse yourself in the rich history and culture of African Americans. The museum's permanent and rotating exhibits are both educational and inspiring.

  • South Street & Love Park: Explore South Street's quirky shops and street art. Snap a classic photo at Love Park with the LOVE sculpture as your backdrop.

  • Reading Terminal Market (Lunch): This bustling market is a feast for the senses! Sample everything from fresh seafood to local cheeses. Insider Tip: Grab a cheesesteak hoagie – a Philly must-have!

  • Spruce Street Harbor Park (Night): Enjoy the lively atmosphere at Spruce Street Harbor Park. Take a scenic ride on the carousel or grab cocktails and relax with stunning city views.

Day 2: Rocky Steps & Rooftop Revelry

Travel advisor Ashlyn stands before the iconic steps of a grand columned building.
  • Rooftop Brunch: Philly has amazing rooftop dining options! Soak in the cityscape while enjoying a delicious brunch.

  • UPenn & Rocky Statue: Walk through the picturesque campus of the University of Pennsylvania. Then, channel your inner Rocky by running up the steps at the Philadelphia Museum of Art, just like in the movie!

  • Philly Historic District: Take a walk through time in the historic district. Admire the colonial architecture and learn about Philly's role in American history.

  • Dallesandro's (Lunch): Refuel with a classic Italian hoagie at Dallesandro's. This family-run shop is a Philly favorite.

Looking for a Night Out? Try:

  • Somo Manayunk: Experience the vibrant nightlife of Manayunk with its trendy bars and restaurants.

  • Attico Rooftop: End your night with stunning views and upscale cocktails at the Attico Rooftop bar.

(Optional) Day 3: NYC Escape

The image captures a serene nighttime cityscape, with a tree-lined path drawing the eye toward a brightly lit central structure.

If you have extra time, consider a whirlwind day trip to New York City! If you head out around 11am, you might even make it back to Philly before midnight!

Morning: Explore iconic landmarks like the 9/11 Memorial and the Statue of Liberty.

Afternoon: Stroll across the Brooklyn Bridge and soak in the bohemian vibes of Greenwich Village. Grab a bite at Chelsea Market, then take a romantic walk-through Bow Bridge in Central Park.

Evening: Head back to Philly, stopping for a slice of legendary cheesecake at Junior's before taking a walk through the many Broadway venues!

Need to know

This itinerary provides just a taste of what Philadelphia has to offer. With its rich history, delicious food scene and vibrant culture, Philly is a city that will leave you wanting more!

Advisor - Ashlyn Terry

Travel Advisor

Ashlyn Terry

Get in touch with Ashlyn

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This itinerary is part of our ongoing series on travel to Philadelphia. For more travel tips, check out Fora Advisor Gillian Spatz's guide, Exploring Philadelphia: A City of History, Culture, and Culinary Delights.