The most important thing to know about Philadelphia is that it’s a master of the high-low. The city that boasts about the epic tasting menus of Vetri, a place Mario Batali has said might be “the best Italian restaurant on the East Coast,” is the same city that has sports fans so rowdy that Lincoln Financial Field, home of the NFL’s Eagles, once required an on-site jail and courtroom. It's where the Declaration of Independence was signed—the birthplace of our democracy—but also a city that's been wracked with political corruption (as if the two were mutually exclusive). It's a city where chefs and mixologists are local celebrities, but where you can still get the same $3 drink special at almost any bar (more on that in a bit). It was home to celebrated artists like Alexander Calder, Mary Cassatt and Andrew Wyeth—but also serves as the backdrop for the misanthropic debauchery of It's Always Sunny in Philadelphia, which returns to FXX tonight. Above all, Philadelphians are fiercely proud of everything that surrounds them—whether they should be or not.

2:26 P.M. A late night out requires coffee—just a simple coffee, not some confection like a hazelnut latte or Frappuccino. Since 1994 La Colombe Torrefaction, Philadelphia’s original artisanal roaster, has brewed an exceptional cup of joe. As such, you’ll find it all over the city. But La Colombe’s café on South 19th Street is where it tastes best. The space reflects the coffee maker’s philosophy—the beans are the only things that matter. The bright room is basic with minimal pastries and no merchandise for sale. Get one of the single-origin brews, e.g., the brightly fruity Tarrazu from Costa Rica.

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2:43 P.M. Take your cup of La Colombe for a stroll through Rittenhouse Square, a mere block away. Just to the southwest of Center City, this beautiful park is surrounded by some of Philly’s best restaurants such as Lacroix; luxury high-rises such as the 1900 Rittenhouse Square Apartments, which was built in 1926 and is now listed on the National Register of Historic Places; and the Curtis Institute for Music, a school so exclusive that it has an even lower acceptance rate than Juilliard. The crowd in the park is eclectic, a mix of wealthy seniors, guitar-toting crust punks, couples and stoned shirtless guys dancing aimlessly.

3:57 P.M. One of Philadelphia's most fascinating pieces of history has nothing to do with the birth of our nation—it’s a prison. In operation from 1829 to 1971, Eastern State Penitentiary was abandoned for several years before finally opening for public tours in the mid-1990s. What's amazing about the penitentiary is how little has been restored; on the walking tour (narrated by Steve Buscemi), you'll see original bed frames still rusting in their cells. And while Eastern State doesn’t have the notoriety of Independence Hall and the Liberty Bell, it has had brushes with fame in the past. The film 12 Monkeys transformed the prison’s rotundas into the insane asylum that housed Brad Pitt and Bruce Willis. It’s also the place where Al Capone first served time. But compared to his fellow inmates, Capone did so in opulence, his cell stocked with fine furniture.

5:19 P.M. Apothecary, Philadelphia’s first cocktail bar, tried way too hard, with an obnoxious, overly slick interior. However, its successor, Franklin Mortgage and Investment Co., understands the difference between elegant showmanship and unnecessary gloss. Thus, the bar has a speakeasy vibe without making you say a password at the door (because really, we're adults). Most important, it serves well-made cocktails that allow you to actually taste the ingredients (because nothing says “bad drink” like mediocre bourbon and cloying fruit-flavored syrup). Two drinks in particular stand out: the Harry Rag, which combines two scotches with Amaro Nonino, green Chartreuse and orange bitters, and Pretty As a Prayer Book, which pairs mezcal and gin with an orange pepper thyme syrup.

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7:30 P.M. Dinner is best served at the Fitler Dining Room, where Robert Marzinsky cooks food that doubles as art. And that’s not a tired cliché either: Marzinksy has a BFA from Alfred University. At Fitler he channels both his inner artist and the lessons he learned cooking under Jonathan Adams at Philly’s top gastropub, Pub & Kitchen. The result is a collection of gorgeous, impeccably flavored meals with French inspiration. (One such meal—fluffy gnocchi with snails and Chartreuse butter.) The cuisine, of course, is seasonal. Currently, the late August menu features Beausoleil oysters with trout roe and duck breast with stone fruit and crispy potato.

10:11 P.M. Almost any bar in Philadelphia offers the “citywide special”—a PBR with a shot of Jim Beam for $3. But the king of local dive bars, Bob & Barbara’s, makes it special (if for no other reason than they did it first, way back in 1969—though there may be some dispute). Plus, depending on the night, you’ll be treated to either karaoke (Sundays), a drag show (Thursdays) or live music (Saturdays and Sundays). While Bob & Barbara’s was originally a jazz bar, the current house band, the Crowd Pleasers (a soulful trio on sax, keyboard and drums), plays what they call “liquor drinking music.”

1:55 A.M. After last call, don't fall prey to the drunk-food cheesesteak duel between Pat’s and Geno’s. Instead, head to Underdogs. Since it’s open until four a.m., it’s a popular post-work spot for Philly’s restaurant elite (chefs, bartenders, etc.). Nothing beats the Penn Deutch—a hot dog served with a codfish cake (the name comes from Pennsylvania Dutch cooking, where fish cakes are a staple). But don’t forget about more standard hot dog fare either—fries, which at Underdogs come with an amazing malt vinegar aioli.

3:13 A.M. When sleep is insurmountable, the Hotel Monaco awaits. Tucked right next to Independence Hall, it provides all the luxury you’d expect from a AAA four-diamond hotel but with modern-looking digs—i.e., it pairs Colonial design elements with bright, bold wallpaper, creating an upscale hotel that doesn’t feel stuffy. Before you leave, make sure you spend some time at the Stratus Lounge. On the 11th floor, this gorgeous bar will give you a great view of the city—everything from the elegant brick buildings where America was founded to the drunk guys standing right outside, yelling “E-A-G-L-E-S!”


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Photo courtesy of Terry Robinson/Flickr