The Philly Curator’s Perfect 3 Day Philadelphia Itinerary
If I were my client, this is the itinerary The Philly Curator would plan for my trip to Philadelphia.
Philadelphia is a city best experienced through its neighborhoods, each with its own rhythm, flavor, and story. This itinerary blends iconic history with local gems, chef‑driven meals, and the kind of insider touches that make you feel like you’re seeing the city and all it has to offer. This is MY perfect 3 days. Your perfect 3 days will represent what you love to see and do. Let me curate the ideal itinerary for you.
DAY 1 — SOUTH PHILLY, MOSAICS & OLD CITY EVENIN
Brunch at Grace & Proper - I’d start my day at Grace & Proper, a European‑inspired corner café known for its cozy vintage charm and beautifully crafted cocktails. It’s intimate, stylish, and the perfect soft landing for your first morning in the city. (If you are in the neighborhood in the evening, Grace & Proper has a very lively happy hour!)
A Wander Through the Italian Market - From there, I’d stroll into the Italian Market, one of the oldest open‑air markets in America. I always stop at Di
Philadelphia’s Magic Gardens
Next, I’d step into Philadelphia’s Magic Gardens, Isaiah Zagar’s immersive mosaic wonderland. It’s whimsical, deeply personal, and unlike anything you’ll see anywhere else — a reminder that Philadelphia’s creativity lives right out in the open. It is not just the Magic Garden that you would find his impressive artwork. It is all over Queen Village, in alley ways, on residents’ houses, on store fronts. There are over 100 mosiac artworks around Queen Village. Mr Zagar is an amazing prolific artist!
Walk South Street + Lunch Options - Continue along South Street, a stretch that’s eclectic, artistic, and full of personality.
Lunch can go in several directions:
Pizzeria Stella for blistered Neapolitan pies (I love the pistachio pizza)
The Twisted Tail for Southern comfort and live‑music energy (not to mention happy hours again, but this space has the best happy hour in the hood!)
One of the many global spots lining the street. I personally love Nam Chon, a small Korean restaurant serving soulful, deeply flavorful dishes.
From these restaurants, you can admire Headhouse Square, one of the oldest public spaces in the country, framed by brick walkways, historic charm and a lively energy that anchors this corner of South Street.
Afternoon at the Museum of the American Revolution
I’d spend my afternoon at the Museum of the American Revolution, one of the city’s most thoughtfully curated museums. It brings the founding era to life with immersive storytelling and powerful artifacts that make history feel immediate and human.
Evening in Old City — Dinner at Royal Boucherie - After a rest at my hotel, I’d head to Royal Boucherie, a French‑inspired brasserie known for its warm glow, exceptional cocktails, and one of the best raw bars in the city. It’s intimate, stylish, and effortlessly cool — very Old City.
And if I’m up for more after dinner, 2nd Street is lined with bars, lounges, and late‑night spots. It’s one of the liveliest nightlife corridors in Philadelphia.
DAY 2 — ICONS, HISTORY & CENTER CITY GLAMOUR
Breakfast at Reading Terminal Market - Start at Reading Terminal Market, one of the great food halls of America.
Walked the entire market and choose what you want to eat for breakfast. There is plenty of seating for your to dine comfortably. Then immediately walk to Beiler’s Donuts for something sweet. (Trust me: get a donut.
Old City’s Historic Core
Today is your deep‑dive into the birthplace of the nation. Move at your own pace through:
The Independence Visitor Center
The Liberty Bell
Independence Hall
Elfreth’s Alley, the oldest continuously inhabited residential street in America
The Betsy Ross House
It’s all walkable, beautifully preserved, and surprisingly moving.
Lunch at Positano Coast
For lunch, step into Positano Coast, a bright, breezy, coastal‑Italian vibes with a beautiful interior and a menu that’s perfect for lunch. It’s a refreshing contrast to the brick‑and‑history of Old City, and the food is consistently good. (I held my son’s 21st birthday party here)
Shopping + Rittenhouse Pause
After lunch, head west to Chestnut and Walnut Streets for shopping. You’ll find a mix of national brands, local boutiques, and the kind of window‑shopping that turns into “just one bag.”
Then take a breather in Rittenhouse Square, a perfect people‑watching park framed by historic townhomes and leafy paths.
Happy Hour on Sansom Street
For happy hour, choose between:
Harp & Crown, with its moody, vintage‑European interior and excellent cocktails and the best happy hour menu in town!
Oyster House, a Philadelphia institution known for pristine seafood and legendary oyster specials. We love their oysters and lobster rolls
Both sit on Sansom Street, where you will find dozens of wonderful restaurants block after block.
Dinner at Parc
End your day at Parc, the beloved French brasserie overlooking Rittenhouse Square. It’s lively, elegant, and quintessentially Philadelphia — the kind of place where every table feels like the best seat in the house. I love their Steak Frites and their Shrimp Salad. Oh, and don’t get me started on their bread baskets. Yum
DAY 3 — ART, HISTORY & A NIGHT IN FISHTOWN
Breakfast at The Love - Begin at The Love, a warm, stylish restaurant from Aimee Olexy and Stephen Starr. It’s known for thoughtful, seasonal dishes and a hospitality style that feels personal and generous.
The Barnes Foundation - Spend your morning at The Barnes, home to one of the world’s most extraordinary collections of Impressionist and Post‑Impressionist art. The intimate, intentional arrangement makes the experience feel like stepping into someone’s private world.
Walk Along Boathouse Row
After the Barnes, take a walk behind the Art Museum along Boathouse Row. The river path is peaceful, scenic, and gives you one of the most iconic views of Philadelphia — a quiet reset before the afternoon.
The boathouses along Boathouse Row aren’t just picturesque — they’re still active today, home to storied rowing clubs like Penn AC, Vesper, Malta, and University Barge Club, as well as university teams from Penn, Temple, Drexel, and Saint Joseph’s, all training on the Schuylkill just as they have for generations. I have spent many a day on these banks while watching my son row on his high school team.
Lunch at Sabrina’s Café - Head to Sabrina’s Café for lunch, a beloved local spot known for generous portions, creative comfort food, and a warm neighborhood feel.
Afternoon at Eastern State Penitentiary
Spend your afternoon at Eastern State Penitentiary, one of the most hauntingly beautiful historic sites in the country. Its crumbling cellblocks, sky‑lit corridors, and award‑winning audio tour tell a powerful story about early prison reform and the people who lived behind these walls. It’s atmospheric, unforgettable, and uniquely Philadelphia.
I would head back to my hotel to refresh before the evening activities.
Evening in Fishtown — After a hotel refresh, I’d take a rideshare to Fishtown, one of Philadelphia’s most energetic dining and nightlife neighborhoods
Happy Hour at Frankford Hall
Start with happy hour at Frankford Hall, an open‑air German beer garden that’s lively, communal, and perfect for easing into the evening. Get a soft pretzel
Then head to Laser Wolf, Michael Solomonov’s Israeli skewer house that’s earned national acclaim. It’s vibrant, flavorful, and one of the most joyful dining experiences in the city. This restaurant is my latest obsession. I can’t get there enough.
Stay out afterward — Fishtown’s nightlife is full of music, cocktails, and that unmistakable creative energy that makes the neighborhood feel alive. I love Stateside and LMNO.
These three days are my perfect way to experience Philadelphia — the places I return to again and again, the neighborhoods that feel like home, and the moments that capture the city at its best. But your perfect three days might look completely different, and that’s the beauty of this city: there’s always another layer, another flavor, another story waiting for you. When you’re ready, I’ll curate a version of Philadelphia that is designed just for you — your pace, your interests, your style — so your trip becomes the one you’ll talk about long after you’ve gone home
