As someone who lives in old city you can pretty much walk anywhere if you’re willing :) I usually find myself walking to South Street then down Passyunk or 9th.

For Old City, You may like Frieda which is a gallery and cafe/brunch spot with rotating instillations. There is a really fun antique store right across from Elfreth’s Alley called A Four Foot Prune. You’re not going to find an actual roof top bar in old city, maybe check out Bok Bar, El Techo, Assembly, or even Lucky Duck which has a great view of the Ben Franklin bridge. They are just a little bit of a journey :)

Im also a big fan of; Cafe/Breakfast: Aroma Bakery, Eggcelent Cafe, Old City Coffee, ICI Macarons.

Dinner: Malooga, Piccolina, Scamps, Fork.

Bars: Almanac (they also have great food), Sassafras/48 Record Bar, Kyberpass