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What to Do in Philadelphia: The Perfect Weekend

By August 28, 2020September 8th, 202028 Comments

Philadelphia, Pennsylvania is much more than Ben Franklin and an old broken bell. I’ve had the pleasure of exploring what to do in Philadelphia over the years, and love the city as a spot for a weekend out-of-town or an east coast road trip stop. I have the low-down on everything from the best margarita in town and the newest penthouse lounge to the best suit-style accommodations and, of course, how to avoid lines at the Liberty Bell. Let’s dive in!

Philadelphia skyline and skyscrapers from one liberty observation deck

  • Where to Stay in Philadelphia
  • Philly Eats
  • What’s New in Philly?
  • The Gayborhood and Nightclubs
  • Museums and History in Philadelphia

Getting to Philadelphia

I’m based in Boston, so it’s about a 90-minute flight to get to Philadelphia. Those near New York City are even closer, about an hour drive or train ride to downtown. Delta is a major hub in Philly for flights from many major cities throughout the U.S. It’s simple to take Route 95 as well, north or south, to reach the city on your road trip (just like our major road trip from Boston to Miami!)

Where to Stay in Philadelphia

Rooftop Chairs at Windsor Suites Phildelphia

The Windsor Suites

It’s best to be somewhat central when visiting Philly and choosing a hotel. I often work and travel – plus I like to have space if I can in a busy city. The Windsor Suites is a fantastic option for these reasons. People staying in town a little longer or those in small groups love the suites, as most rooms offer full kitchens (like oven, stovetop and regular-sized fridge) along with a spacious bedroom and sitting area. They are basically small apartments. This is ideal if you want to pick up some grazing food from Reading Terminal Market, or store some breakfast to-go so you can get to exploring Philadelphia early. There’s a sunny pool deck on the roof as well that is ideal for a quick soak or Vitamin D session in between boughs of sightseeing.

Windsor Suites Philadelphia outside buildingOther Philadelphia options

Airbnb is alive and well in Philly and a good option if you’d like to explore some of the neighborhoods away from downtown. If you prefer some classic and upscale, the Four Seasons is a brand new option in the Comcast Center (look below for our review on the sky lounge!) I prefer using Hotels Combined if you like to compare various rates for your travel dates.

Where to Eat in Philadelphia

Alright, let’s get this out of the way. You all really came to Philly to stuff yourself with Cheesesteak, right? A ‘cheesesteak’ is simple – hoagie bread, cheese, steak (or veggie equivalent that’s your jam). Now how this is done is hotly contended though. Some swear that the ONLY way to eat this is with actual orange cheese whiz. Others say American or Provolone cheese is a must, with peppers, onions, and/or mushrooms. Toast the bun? Maybe. Sirloin steak over ribeye? You be the judge.

On my various trips to Philly I’ve had a dozen or so of these babies – and none of them, so far, have been bad. I’m not even going to try to weigh in on the best, because it’s going to be up to you and your palette. Personally, the greasier the better for me!

Subway and green trees outside city hall philadelphia (1)Jim’s Steaks

This was the first cheesesteak I ever had in the city, recommended by a local friend. Jim’s Steaks claims to have been around since 1939 and the locations still sport an art-deco diner design. If you’re really hankering for one of these cheesesteaks, you can actually order them through Goldbelly too from anywhere in the country.

Pat’s King of Steaks and Geno’s are the other two top contenders for the cheesesteak crown. Pat’s claims they invented the cheesesteak in 1930 and really say it’s only good with cheese whiz product. You should try them all and be the judge. Read onto to find out about the cheesestakes in Reading Terminal Market too!

Parc for Mimosas and Brunch

To start off the day with a Parisian twist, Parc is ideal for dining al fresco when the weather is nice. The have a wonderful raw bar for brunching, and lots of fresh baked French pastries to indulge. For something more substantial, they offer classic dinner dishes as well, such as Duck L’orange and Steak Au Poivre.

Reading Terminal Market

By far, the best eating experience I had outside of stuffing my face with cheesesteak is the Reading Terminal Market. I spent a whole afternoon there poking around, as it’s the city’s oldest market at more than a century of history. There are more than 64 vendors. Here’s some of the highlights.

  • Eight Oaks Farm Distillery

A nearby craft distillery offers some of the state’s finest spirits, from Whiskeys and Bourbons to Gin and Vodkas. You’re welcome to taste them all. I loved the cranberry infused vodka and took home a bottle of whiskey for my husband. Staff was super friendly and happy to chat about all their different varieties.

  • Spataro’s Cheesesteaks

More cheesesteaks! I thought this was a decent contender, and no line to wait in either. I chose a classic cheesesteak with onions and American cheese, whipped up on the flattop grill in front of me. Cheap and cheerful, big enough to at half and take the rest back to your hotel for later.

  • Miller’s Twist

ice cream cone in reading terminal market in Philadelphia

There’s a couple spots to get ice cream in Reading Terminal, but I thought this hard packed, homemade variety was tops. Miller’s actually specializes in pretzels, but I enjoyed their peanut butter swirl ice cream flavor the most.

  • Pearl’s Oyster Bar

A raw bar right in the middle of the market is an upscale choice for happy hour. The seafood is delish and Pearl’s has been around for decades serving local delicacies and national classics.

  • Old City Coffee

All that eating can get you tired – luckily, there’s a great small-batch roaster right in Reading with some strong concoctions ready to go. Since 1985 they’ve offered roasted coffee by the bag and by the cup onsite. Try the Iced Americano, or the coffee of the day.

El Vez in gayborhood for Mexican

Every great Mexican food joint has to have an exhaustive tequila list, right? I love El Vez every time I’m in town, as it’s ideal for a strong drink and a few charing plates. Any meal that starts with just melted manchego cheese and ends with carne asada and plantains is perfect in my book.

Nightclubs in Gayborhood

street art and blue sky in Philadelphia

Speaking of El Vez, you’ll want to linger a bit longer in this area of Philly, affectionately (and officially?) known as the ‘gayborhood’. I never understood why Boston didn’t have space like this in our city, as it’s a wonderful haven of restaurants, bars and nightclubs that welcome all in the LGBTQ community.


Every time I go to Woody’s, I wish Boston had something similar for it’s gay community. All camp and kitsch, this bar has been around forever. Downstairs is a large sport-club-ish floor with a more causal drinking feel. Upstairs is where the magic happens, with themed dance nights and a regular rotation of top DJs. It’s mostly frequented by gay men – so if you do want to hang there and you’re of another persuasion, just keep it cool and respectable.


I went here when it used to be iCandy to have a few filthy-named cocktails on the tiny rooftop bar. It’s been recently upgraded and is super popular to dance and cruise all night long.

Toasted Walnut

This one is for the ladies. Toasted Walnut is a laid-back spot for an early drink that gets rowdier as the night goes on. As most bars in the neighborhood, the crowd is welcoming and eclectic, with this one learning more towards lesbians. They have drink specials on the regular, tasty food and a hot pink LED bar.

Museums and History in Philadelphia

city hall and blue sky in Philadelphia

Sometimes I think we travel, assuming the dusty places like museums will just….always be there. But if you don’t wander into some of these marvelous institutions, you’re really missing out. Here’s all of Philly’s best museums, as well as it’s classic historic landmarks to give you a repertoire of great things to do in Philadelphia.

Independence Hall and Independence National Historical Park

This space is a certified U.S. National Park – one of the few in a downtown city! There’s a museum dedicated to Ben Franklin, and tours available to see Independence Hall up close, where the Declaration of Independence was signed.

You’ll also find the famous Liberty Bell there too. You’re welcome to stand in line (no ticket needed) to see the historic bell up close. Or, you actually can round the corner and get a decent view through the glass without the lines if you’re not bothered about getting inside the building itself.

Philadelphia Museum of Art

rocky steps and museum in Philadelphia

This is it – the stairs leading to the Philadelphia Museum of Art are the famous steps from the Rocky II movie. You can climb them too like Sylvester Stallone did in his fight training montage. You might as well, because everyone’s doing it while singing Eye of the Tiger!

But don’t forget to actually visit the museum at the top. Its known for a few famous masterpieces, including Renoir, Monet, Manet, Degas, and Cézanne. This visit, I loved the temporary Japanese exhibit, Yoshitoshi: Spirit and Spectacle. Check in advance to see what’s on for your trip. There’s also some super interesting room installations to mimic various designs over time. I enjoyed the turn-of-the-century Manhattan-esque room with incredible period furniture, as well as the Japanese teahouse. Don’t miss the modern art wing as well for some though-provoking works.

Philadelphia City Hall

This is the largest municipal building in the U.S., and one of the grandest in Philadelphia. You can take one of two tours – either see the interiors or, if feeling sprightly, climb the nearly 550-foot tower topped with a statue of Willam Penn.

Delaware Riverfront

margarita at the delaware riverwalk in Philadelphia

My local friend brought me about a 20-minute walk from the Gayborhood to the riverfront. This area isn’t as developed as downtown, but is a super laid-back area where a lot of students and hipsters hang. There’s a small boardwalk lined with a few bars and casual restaurants, flanked by the occasional live music busker or performance. Beyond this is some funky seating areas along the water, including old nets hung over the river for lounging and drinking.

Mutter Museum

Mutter Museum lobby Philly

Now, I don’t even know if I can actually say you should go here. I might have skipped it myself! Bu those who have a somewhat morbid curiosity might find this particular place fascinating. The collection has been protected and curated by the College of Physicians of Philadelphia. For admission, you can see some medical oddities and, well, body parts up close. Some of the more famous (and tame) exhibits include part of Albert Einstein’s actual brain and a preserved conjoined twin fetus. The whole thing made me shutter, especially the skin diseases and temporary war wound exhibition. Yikes. But if this would interest you, go for it!

One Liberty Observation Deck

ben franklin's head at the Philadelphia one liberty observation deck

This is the city from above! Grab a ticket an head up 57 floors to the newly renovated observation deck on the One Liberty building downtown. They have fun mini exhibits to have you learn about music, history and more in Philly as you walk 360 degrees around the deck. Use interactive screen to peep information about the views you see too. It was a lovely, calm area to observe the bustling streets below.

What’s New in Philly?

Now that I’ve checked out Philadelphia a few times over the years, I’ve noticed fresh things popping up constantly downtown and beyond.

JG Skyhigh in the new Four Seasons

Four Seasons Skyhigh Lounge in Philadelphia at night

The newest It-Cocktail-Bar is at the Four Seasons. They’ve created the city’s chic hotel at the top of the Comcast Center, complete with restaurant by Chef Jean-Georges and lounge area. You can visit for a drink at the bar, which is well worth it. Dress to impress and be rewarded with skyline views and twinkling city lights at night from the towering glass ceilings over the JG Skyhigh. Their wine list is extensive, and the cocktails are classically divine. Arrive early if you’d like a spot by the windows or in the small seating area.

Philly’s First Micro Hotel

I travel a lot for business and love simple, clean accommodations close to all the action. I’m excited to hear about Philly’s new ‘pod’ hotel and their useful amenities, such as free Wifi and private bathrooms. It might be great for a quick stay or even a bachelor party who’d like their own private rooms and bathrooms after a long night out on the town.

Have you been to Philly? What was your favorite thing to do in Philadelphia? What other east coast cities to do love? Thanks so much to Visit Philly for hosting!

Eileen Cotter Wright

Author Eileen Cotter Wright

Eileen Cotter is a freelance travel journalist and owner of Pure Wander. She's our resident expat extraordinaire and falls down a lot in yoga class. Follow her on Instagram @Pure_Wander.

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