Philadelphia, depending on who you ask, is either a city steeped in history or a hub of innovation. Then again, it’s best known for its passionate sports fans or its world-class museums. Or for its cheesesteaks—or its restaurant scene that’s quietly become one of the country’s best.
As a born-and-raised Philadelphian, I think the city is great because it is or has all of those. You can walk through Old City and wander the rooms where American democracy was born 250 years ago or admire the world’s largest collection of Renoir paintings in the intimate, jewel-box galleries of the Barnes Foundation. You can stroll past the country’s first hospital, founded in 1751 by Benjamin Franklin, or trace the Schuylkill River Trail alongside joggers, bikers, and rowers. You can taste your way through century-old market stalls and boundary-pushing fine dining. All the while, you’re experiencing one of the most vibrant, contradictory cities in America: gritty and polished, familiar yet full of surprises.
“There is a resourcefulness and creativity to Philly—in the food, in the parks, in the streets,” says Lindsey Scannapieco, founder and managing partner of Scout, the urban design firm behind South Philly creative hub the Bok building. “I honestly think it’s the best city in America.”
Still need convincing? Read on for how to spend four unforgettable days in the City of Brotherly Love.
Elfreth’s Alley dates to 1702 and has always been cobblestoned.
Photo by f11photo/Shutterstock
Day 1: History, shopping, and late-night cheese
Before diving into a day exploring American history, fuel up at Fiore in East Kensington, which plates regional Italian pastries and creamy eggs and ricotta tucked into house-made focaccia. Afterward, head south on SEPTA’s Market-Frankford Line (or take a short Uber ride) to explore Old City’s founding-era landmarks, all of which will be a centerpiece of next year’s 250th anniversary of the nation’s birth. Start at the Liberty Bell Center to see the famous cracked iconHistory buffs shouldn’t miss a tour of Independence Hall to see the rooms where the Declaration of Independence and the Constitution were debated and signed. (For a $1 admin fee, you can book timed tickets in advance. If time allows, add Museum of the American Revolution (Washington’s original field tent is the star), the Betsy Ross House, where the famed seamstress designed the American flag, and cobblestoned Elfreth’s Alley, the nation’s oldest continuously inhabited residential street, to your agenda.
For lunch, bring cash and plan to wait in line for a requisite cheesesteak at the celebrated Angelo’s Pizzeria, finished with your choice of melted Cooper Sharp or long hot–spiked Cheese Whiz. If you prefer a more relaxing, sit-down meal, book a table at High Street for sourdough pizzas and bright salads.
Stroll to Cherry Street Pier, a onetime municipal pier turned cool public space with Delaware River views, resident-artist studios, and an open-air garden. Continue south to Head House Square and Fabric Row on South Fourth Street, dense with boutiques, vintage shops, and indie bookstores. Pop into the Merrygold Shop for charming gifts like butter-shaped hair clips and small-batch tea, Good Good Chocolates for glossy, made-on-site bonbons, Moore Vintage Archive for high-end vintage clothing, and Head House Books, one of the city’s most beloved bookstores.
Kalaya’s chef Chutatip “Nok” Suntaranon serves food inspired by her Thai childhood.
Photos by Ted Nghiem
Jo Piazza, the Philadelphia-based author of national bestsellers Everyone Is Lying to You and The Sicilian Inheritance, recommends spending an afternoon in one of their armchairs with a good book. “They have a perfectly curated selection of novels, nonfiction, and kids’ books,” she notes.
Head back north for dinner to the Fishtown neighborhood, home to some of the city’s best restaurants. Make a reservation far in advance for southern Thai curries at award-winning Kalaya or lamb neck birria and seasonally changing tlayuda at modern Mexican restaurant Amá.
Afterward, settle in for a nightcap at Mural City Cellars, Philly’s first independent urban winery, where you can sip a pet-nat rosé in the dimly lit tasting room steps from where the wine is made. Before turning in for the night, pick up a snack at Perrystead Dairy. There, a 24-hour vending machine, stocked with cheese and crackers and spreads, guarantees that visitors can purchase a puck of semi-soft cheese washed in seawater, or one of cheesemaker Yoav Perry’s other award-winning varieties, no matter the hour.
The abstract sculptures of Alexander Calder pop alongside the stunning landscaping of Calder Gardens.
Photo by Iwan Baan/Calder Gardens
Day 2: Art museums, gardens, and a historic market
Start the morning at K’Far in Rittenhouse. Order a Jerusalem bagel breakfast sandwich and carry it a block to John F. Collins Park, a leafy “pocket park” tucked off Chestnut Street that’s akin to a secret garden in the middle of Center City, according to Scannapieco.
Next, head for the western end of the Benjamin Franklin Parkway. Pass the bronze Rocky at the base, then mimic the fictional boxer’s climb to the Philadelphia Museum of Art, which houses more than 200,000 objects whose origins span over 2,000 years.
For lunch, roam Reading Terminal Market. Join the line at DiNic’s for a roast pork and broccoli rabe sandwich or Sang Kee for Peking duck, then finish with a scoop of salted caramel pretzel ice cream at Bassetts, still serving at its original marble counter, as it has since the 1890s.
The bar is very much where it’s at when you visit Friday Saturday Sunday.
Photos by Ted Nghiem
Devote the afternoon to more art on the Benjamin Franklin Parkway, starting with the Barnes Foundation, home to one of the world’s great Impressionist and early modern collections. Across the street, Calder Gardens is an essential visit. The sleek new space is home to abstract mobiles and sculptures by artist and native Philadelphian Alexander Calder and includes some 250 varieties of plants envisioned by famed landscape architect Piet Oudolf (who also designed New York’s High Line landscaping.) “I’m really excited to see the Calder Gardens as they grow,” says Scannapieco, a self-proclaimed “huge fan” of Oudolf.
Dinner is on North Broad at Honeysuckle, Omar Tate and Cybille St. Aude-Tate’s Afro-centric restaurant that blends storytelling and seasonal mid-Atlantic ingredients into a deeply personal, deeply delicious meal.
If you didn’t snag a reservation there—or you feel energetic enough for one more stop—head to the downstairs bar at Friday Saturday Sunday, one of Philly’s most celebrated restaurants. Piazza, who sidles up to the bar for one of their artisanal cocktails and a plate of smoked herring spaghetti at least once a week, says, “We are early birds when it comes to dinner and cocktails.”
Hop on a two-wheeler and tour the banks of the Schuylkill River. You can even spot Boathouse Row (right).
Photo by Jana Shea/Shutterstock (L); Sean Pavone/Shutterstock (R)
Day 3: Parks, river trails, and an ’80s-inspired Japanese izakaya
Kick off day three with a coffee-and-pastry run to Vernick Coffee Bar, a polished lobby café in the Comcast Technology Center. From here it’s a short walk to the city’s riverside greenway. “Schuylkill River Trail is one of my favorite places to bike, run, and even kayak,” says Piazza. “You can rent boats from Hidden River Outfitters to see the city from a whole new perspective.”
Push on into sprawling Fairmount Park for a greatest-hits loop: Shofuso, a midcentury Japanese house and garden, transplanted to Philadelphia in 1958 and set amid pines and koi ponds; Boathouse Row, where you can spot rowers climbing into their sculls; and Smith Memorial Playground, where the century-old wooden slide—immortalized on the Philly-based TV show Abbott Elementary—thrills a new generation of schoolkids.
On weekends from April to October, you can head south to FDR Park for the Southeast Asian Market, a joyful community food fair. “The Southeast Asian Market in FDR Park is one of the most special places,” says Scannapieco. “Plus, the park’s home to boating, fishing, and a great playground.” Pick up grilled skewers and chicken wings stuffed with lemongrass-scented vermicelli and wander the 348-acre green space, designed by Frederick Law Olmsted (of Central Park fame) and his brother, John Charles Olmsted.
Wrap up the day back in Center City, at Dance Robot, the buzzy, ’80s-inspired Japanese izakaya from sushi pro Jesse Ito. The kitchen, led by chef Justin Bacharach, is churning out genius twists on comfort food dishes, such as wagyu roast beef with dashi gravy and French onion soup with house-made Japanese milk bread croutons and shiso oil.
From up high, you can catch the sunset rays or hang out on the rooftop Bok Bar.
Photo by Brandon Bliss/Unsplash (L); photo by A. Ricketts/Visit Philadelphia (R)
Day 4: Breakfast inside a former high school, outdoor art, and a tour of the Italian Market
South Philly is home to tight-knit rowhouse blocks and century-old food traditions as well as a flourishing art scene and a wave of new artistic energy. Start at the Bok building, a 1938 former vocational high school reborn as a creative and entrepreneurial hub. Grab coffee at Two Persons, savory croissants at Machine Shop, and a fudgy, salt-dusted brownie from Second Daughter on the fourth floor. Consider returning in the evening for Irwin’s modern Sicilian fare and the seasonal rooftop Bok Bar—both on the eighth floor with knockout skyline views.
As you head north, keep an eye out for artist Isaiah Zagar’s kaleidoscopic mosaics decorating facades and alleyways across South Philly, as well as vivid paintings splashed on the side of rowhouses and buildings from Mural Arts Philadelphia, the nation’s largest public art program. One under-the-radar South Philly landmark: Keith Haring’s 1987 “We the Youth” in Point Breeze, the artist’s only remaining intact public mural that was completed in collaboration with local teens.
Make your way to the South 9th Street Italian Market, one of the United States’ oldest open-air markets, born of turn-of-the-century Italian immigration and now mixed with excellent Mexican and Vietnamese vendors. For context, and curated tastings that include everything from cannoli to banh mi, book a Tiny Table Tours “Beyond the Italian Market” tour. Then browse Fante’s Kitchen Shop (a century-old cook’s paradise), tuck into tortillas and moles at Blue Corn, or join the line for Cristina Martinez’s South Philly Barbacoa—her James Beard Award proves the wait is worth it.
If you’re still hungry, detour to John’s Roast Pork for the namesake roast pork or a top-tier cheesesteak, or pop into Mighty Bread’s East Passyunk bakery for pastries and seasonal toasts using fresh-cut sourdough slices.
Art fans should save time for Philadelphia’s Magic Gardens on South Street, Zagar’s immersive indoor-outdoor mosaic space decked with tile, glass, mirrors, and found objects. Finish with dinner at Mawn, Phila and Rachel Lorn’s intimate Cambodian “no-rules” noodle house in Bella Vista—one of the city’s hardest reservations and a national critics’ darling thanks to dishes such as punchy Burmese ginger and melon salad and spicy khao soi.
Shannon Maldonado, left, anchors her hotel and shop, Yowie, on South Street.
Photos by Ted Nghiem
Where to Stay
Yowie Hotel
On a lively stretch of South Street in Queen Village, Yowie is a boutique hotel above a beloved design shop of the same name. Beyond the classic brick facade, 13 suites are designed like creative studio apartments—colorful, minimalist, and filled with art and objects by local artists (much of it for sale in the shop). With independent check-in and kitchenettes, it’s ideal for travelers who want a local feel and breezy walks to the Italian Market, Magic Gardens, and Old City.
Hotel Anna & Bel
Hotel Anna & Bel anchors a quiet corner of Fishtown (Susquehanna & Belgrade, which lends the name) in a meticulously restored 18th-century complex that once housed a women’s asylum. The 50-key property mixes historic bones with contemporary art, warm textures, and plant-filled spaces wrapped around a seasonal courtyard pool. Stay here for easy access to neighborhood restaurants, shops, and galleries, plus the on-site Sardinian and Corsican restaurant Bastia.
Guild House Hotel
Guild House Hotel occupies an 1850s Italianate rowhouse—once the headquarters of New Century Guild, one of the first groups in the country devoted to supporting working women—on Locust Street in Washington Square West. Inside the 12 artful suites are restored historic details and plush contemporary design. It’s a stylish stay for those who want to be in the center of it all.
