28 Perfect Date Ideas in Philly: Romantic Dates for Philadelphia Foodies, Music Fans, & More!

When it comes to planning the perfect date in the Philly area, the challenge isn’t finding something fun and romantic to do–it’s choosing just one of the countless amazing options Greater Philadelphia has to offer! Luckily, it’s hard to go wrong with any of the date ideas on this list.

A First Look at Philadelphia’s Top Date Ideas:

  • Best Philadelphia Date Idea for Indecisive Eaters: Reading Terminal Market
  • Best Philly Date Idea for Foodies: A Couple’s Cooking Class at La Cucina at the Market 
  • Spookiest Philly Date Idea: Philly Ghosts Haunted Dark History Walking Tour 
  • Most Adrenaline-Pumping Philly Date Idea: Rock Climbing at the Cliffs at Callowhill 
  • Most Competitive Philly Date Idea: MindEscape Escape Room
  • Best Philadelphia Date for Creatives and Art-Lovers: Philadelphia Museum of Art
  • Best Active Philly Date Idea: Schuylkill River Trail Hike
  • Best Date Idea for Music Lovers in Philly: Chris’ Jazz Cafe

1. Reading Terminal Market: Best Philadelphia Date Idea for Indecisive Eaters

Can’t choose just one restaurant for your date? Not to worry–a trip to the world-famous Reading Terminal Market, a Philly standby since 1893, means you won’t have to. We’ll let the market’s almost dizzying array of options speak for themselves:

  • Beck’s Cajun Cafe, which offers New Orleans dishes like gumbo and jambalaya, Cajun-style breakfast po’ boys, and Southern delicacies like deep-fried mac and cheese and shrimp and crawdad pasta. (Is your mouth watering already? I know mine is!)
  • Careda’s Caribbean Cuisine, where chef Careda Matthews serves Caribbean dishes like oxtail, fried and steamed fish, and of course, jerk chicken. Careda’s jerk chicken was described by one happy customer as “to die for–it really scratched my itch.” 
  • Carmen’s Famous Italian Hoagies & Cheesesteaks sells a classic cheesesteak with peppers, mushrooms, and onions. But they also provide some more unorthodox takes on the cheesesteak (“cheese-takes,” if you will): the apparently patriotic Franklin cheesesteak, with American cheese and Philadelphia-brand cream cheese, and the Kamikaze cheesesteak, with hot peppers, hot sauce, and pepper jack cheese.

As much as we’d love to, we can’t describe every last one of Reading Terminal Market’s eateries in detail. But here are a few more of the numerous cuisines represented at the Market:

Even better, a date at Reading Terminal Market doesn’t have to end when you’ve both eaten your fill. Visit the Market’s merchants selling arts, crafts, and gifts, like Contessa’s French Linens for “an array of imported and American-made table linens to fit any color scheme” or Little Marrakesh Bazaar for authentic, handcrafted products created by Moroccan artisans.

2. A Couple’s Cooking Class at La Cucina at the Market: Best Philly Date Idea for Foodies

We acknowledge that there are two categories of foodies out there: foodies who prefer to eat high-quality, creative, interesting food cooked by other people, and foodies who love to cook (professionally or for their own enjoyment). This Philly date idea is geared toward the foodies who love cooking–that is, anyone who’d be excited to be taught to cook a new recipe, or perhaps to perfect a beloved recipe or technique. 

We’re specifically recommending La Cucina at the Market for this date idea because their cooking classes are widely considered to be among the best of their kind in Philadelphia. The school, which focuses primarily on Italian cooking, even has cooking class “Date Night” events geared toward couples. 

For instance, they recently advertised a “Seafood Festa Date Night” at which couples would learn to prepare a “six-course feast of seafood delights”: “cannellini and tuna crostini, miniature red pepper crab cakes, shrimp scampi over handmade spaghettini, baked branzino, roasted autumn veggies, and citrus and fennel salad.” At their “Indian Cooking Date Night,” couples learn to prepare Northern Indian dishes like lentil stew, curry chicken, and palak paneer. 

What better way to bond with a date–whether it’s your first date, or your thirtieth anniversary–than over a plate of delicious Italian food that the two of you prepared together?

3. Philly Ghosts Haunted Dark History Walking Tour: Spookiest Philly Date Idea

Fans of history and scary stories alike will enjoy an after-dark walk through Philadelphia’s Old City, one of the oldest residential neighborhoods in the U.S. For $30 per person, you’ll visit landmarks like the Liberty Bell, Independence Hall, the Tomb of the Unknown Soldier of the American Revolution, and Bishop White House. A standard tour contains eight stops, lasting about an hour across a distance of about a mile, while the extended tour includes 12 stops, spanning 90 minutes and 1.5 miles.

As you explore each historic landmark, you’ll benefit from the depth of knowledge and enthusiasm of tour guides like Steve, who one reviewer on Tripadvisor called “the best tour guide I’ve ever had. His in-depth knowledge and obvious passion for the history of Philadelphia made for a very informative and entertaining evening.” Another wrote, “Steve was super knowledgeable, enthusiastic and friendly – he really sold the whole experience!”

An additional benefit: sometimes a shared fright feels like a good excuse for you and your date to cozy up to one another! This terrifying walking tour might actually help bring the two of you closer, in addition to teaching you some new details about the haunted history of your city.

  • Website: https://phillyghosts.com
  • Phone number: (844) 757-5657
  • Address of tour meeting location: 217 W Washington Square, Philadelphia, PA 19106

4. Rock Climbing at the Cliffs at Callowhill: Most Adrenaline-Pumping Philly Date Idea

One Yelp reviewer called the Cliffs at Callowhill “an extremely well-designed facility with lots of helpful staff members,” while another describes it as “brand new, clean, and well maintained.” If you and your date are the thrill-seeking types, you can seek thrills safely with a date at the Cliffs, which happens to be the largest indoor climbing gym in the state.

At the Cliffs at Callowhill, options include one day of all-day access for $22 per person, an intro to climbing class for $39 where they’ll show you the ropes, so to speak, or several more intensive membership options that will be worth it if you plan to return again and again. 

Whatever you choose, you and your date will end your day of rock climbing having enjoyed plenty of endorphins and gotten to know each other better.

  • Website: https://movementgyms.com/callowhill/
  • Phone number: (215) 444-7625
  • Address: 1010 Callowhill St, Philadelphia, PA

5. MindEscape Escape Room: Most Competitive Philly Date Idea

An escape room is an adventurous date idea that puts more pressure on participants than the average date. Some of us will want to run screaming in the other direction in the face of such a challenge, while others welcome a little bit of friendly competition. In fact, some of us even thrive under pressure, and want to show off that side of ourselves to our dates! 

There’s also a practical reason to choose an escape room as a date activity: if you’re trying to get to know someone better, it’s an effective way to do that. People’s genuine personalities emerge under a little bit of (playful) stress, especially while dealing with the often frustrating experience of trying to solve a puzzle. And if you and/or your date have a knack for solving puzzles, it’s a great way for either of you to advertise those mental assets. 

MindEscape is far and away the top-rated escape room in Philly, which is why we’re recommending it as our escape room of choice. They describe themselves as a “boutique escape room,” and offer three different escape room experiences with different aesthetics and of varying difficulty: “A Murderer Most Foul,” “Trouble in Paradise,” and “Alice in Wonderland.” 

6. Philadelphia Museum of Art: Best Philadelphia Date for Creatives and Art-Lovers

The Philadelphia Museum of Art’s website describes it as “the cultural heart of a great city—the place for creative play, with a surprise around every corner.” If this sounds like an appealing destination for a date, browse the museum’s calendar to see if you might want to invite your beau to any upcoming exhibitions or events.

An especially good time to visit the galleries is on Friday nights, when they are open from 5 to 8:45pm and admission is pay what you wish. On these evenings, parking is just $5, and the museum hires live musicians and serves local wines and spirits to visitors. 

Consider planning a Friday date night where you spend several hours at the Philadelphia Museum of Art while sipping a drink or two, then visit your favorite nearby restaurant or try out somewhere new for a leisurely late dinner.

  • Website: https://philamuseum.org
  • Phone number: (215) 763-8100
  • Address: 2600 Benjamin Franklin Parkway, Philadelphia, PA 19130

7. Schuylkill River Trail Hike: Best Active Philly Date Idea

The picturesque Schuylkill River Trail is proof that not only are there lots of beautiful trails easily accessible from Philly–you don’t even have to leave the city to reach them! The trail begins in downtown Philly. Amazingly, although only about 70 miles are open for public use yet, it will eventually stretch for 120 miles through southeastern PA, all the way to Frackville in Schuylkill County.

For your date, the two of you can hike as far as you like, remaining within the city limits or venturing out to less urban sections of the trail. It’s frankly worth staying in Philly, though, as some of the notable landmarks you may pass on this hike include:

Each of the landmarks on that list could be a date in and of themselves! So here’s another idea: depending on how much time you both have, consider combining your hike with a visit to the Barnes Foundation, Bartram’s Garden, the Franklin Institute, or any of the other institutions you pass during your outing. You’ll have planned a date that incorporates fresh air and culture in equal measure!

8. Chris’ Jazz Cafe: Best Date Idea for Music Lovers in Philly

Impressively, Chris’ Jazz Cafe has the distinction of being “the longest continuously operating jazz club in the history of Philadelphia. The cafe has attracted immensely talented performers like the Count Basie Orchestra, Junior Mance, Pat Martino, Joey DeFrancesco, and Kevin Eubanks. DownBeat Magazine even included Chris’ Jazz Cafe on its list of the “106 Clubs Where Jazz Thrives.”

Invite your date to Chris’ Jazz Cafe for an evening of skilled live jazz performances, delicious drinks, and satisfying Southern cuisine. It’s hard to imagine a more romantic way to spend an evening.

20 More Fun & Romantic Date Ideas in Philly 

Whether you agree or disagree with our choices, please leave your thoughts on our picks for the best date ideas in Philadelphia in the comments. We’d especially love to hear any cute, interesting, or even embarrassing stories you might have about your own dates anywhere in Philly.

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