DAY 1 | SATURDAY

9:30 a.m. The coffered Champagne-colored ceilings are as orderly as honeycomb. The chandeliers hang like art deco stalactites. Ascending from the grimy bowels of 30th Street Station into the celestial splendor of its grand hall is an arrival befitting one of America’s great cities.

9:50 a.m. A cafe, boutique and 13 design-forward suites fill out the brick corner building that houses Yowie, an ideal home base for exploring the city. Art-directed by owner and fashion veteran Shannon Maldonado, the hotel’s design references McDonald’s Fry Kids, tennis’s Williams sisters and Beetlejuice—all detailed in the in-room lookbook. Check-in starts at 4 p.m., so drop your bags off and head back out.

Insist on more traditional lodgings? The serene, neutral-on-neutral rooms and knockout indoor infinity pool at the Four Seasons offer unmatched views from the Comcast Technology tower in Center City.

10:10 a.m. From Yowie, a half-mile walk south will take you into the Bella Vista neighborhood to visit one of the oldest community arts schools in the country, Fleisher Art Memorial. Take a spin through galleries showcasing work by faculty and students, and end your tour at the complex’s centerpiece, the Sanctuary, a deconsecrated Episcopal church famous for its stunning stained-glass rose window.

11 a.m. In the 1920s, Italians came to Philadelphia en masse, but that’s just one chapter in South Philly’s immigration story, which food writer Maddy Sweitzer-Lammé explores on her Beyond the Italian Market Tour, bookable online. During the three-hour walk, you’ll not only snack at Italian legends such as Isgro’s Pastries but visit Plaza Garibaldi for huitlacoche quesadillas and Ba Le Bakery for pork banh mi, or as they’re known around here, Vietnamese hoagies.

2 p.m. After the tour, pop into some iconic Bella Vista and Queen Village shops. Peruse pizzelle presses and ravioli stamps at the 118-year-old Fante’s Kitchen Shop.

2 p.m. Try on limited-edition Air Jordans at Suplex, oracle of Philly’s deep sneakerhead culture.

2 p.m. Comb the literary arcana for sale at Brickbat Books, whose crammed floor-to-ceiling shelves are equally likely to reveal a 1970s art manifesto, an illustrated Vonnegut novel or an out-of-print fantasy paperback.

5 p.m. When you’ve rested back at Yowie, venture into Philly’s vibrant Chinatown for its art, starting with the elaborate 40-foot Friendship Gate rising over the intersection of North 10th and Arch Streets. Head into the Fabric Workshop and Museum (free, with a suggested donation of $5), where Risa Puno’s sorbet-hued “Group Hug” exhibit ruminates on caregiving.

5 p.m. Then walk over to Wonderspaces, a collection of 16 immersive multimedia installations produced with synchronized lighting, giant inflatable sculptures and psychedelic projections.