Going on an adventure with the boys is an enticing thought and one of the most under appreciated destinations for a boys trip is Philly. It's literally the "City of Brotherly Love" and is packed with craft beer, artisinal food, history, movie sites and more. We think Philadelphia is a hidden gem that more guys should know about. There are tons of things to do here, from restaurants and bars to the obvious long list of historical sites, and of course, this is where Rocky was from, so there are plenty of movie sites to visit, too. But if you're looking to get away with the boys, Philadelphia also offers a ton of unexpected places and experiences to keep you occupied and happy. So, let's take a look at some of the best things to do do in Philly for men!
What Do You Call Your "Guys Trips"?
- Philadelphia offers a mix of historical and fun activities, including running up the steps of the Philadelphia Museum of Art like Rocky and exploring a variety of iconic movie sites.
- The city's food scene is a highlight, especially the famous cheesesteak rivalry between Geno's Steaks and Pat's King of Steaks, emblematic of Philly's rich sandwich culture.
- Visit significant historical sites, such as the Eastern State Penitentiary, once the most famous and expensive prison in the world, now a haunting reminder of past penal philosophies.
- Philly's sports culture is vibrant and passionate, making attending a game, whether it's the Phillies, Eagles, Flyers, or Sixers, an exciting and quintessential Philadelphia experience.
Run Up the Stairs of the Philadelphia Museum of Art
This is pretty much a required thing to do for a guys weekend in Philadelphia, so get ready. We're going to run in the steps of Rocky up to the Philadelphia Museum of Art and then take photos with the statue located adjacent to the steps. This is actually a great museum but sweaty guys shouting their favorite Rocky quotes is a great way to kick off your guys weekend!
Grab a Cheesesteak and Argue About Who's Is Better
While Philly locals all have their own favorite cheesesteak place, and many of them chose places other than the famous Geno's Steaks and Pat's King of Steaks, this is a required stop when you visit here. The two properties are located on the same corner of South 9th Street and Passyunk Ave so this is an easy way to get your debate on experience part of Philly's legendary food culture.
If cheesesteaks aren't your style, don't worry! This is a SANDWICH CITY and someone has the right combo for you, so keep searching :)
Reading Terminal Market
This historic market is a food lover's paradise and the perfect spot to fuel up before a day of activities or recover from the previous night's festivities. Housed in a former railroad terminal since 1893, Reading Terminal Market offers everything from classic Philly cheesesteaks and roast pork sandwiches at DiNic's (voted "Best Sandwich in America" by the Travel Channel) to Amish breakfasts and local specialties. The best strategy is to divide and conquer – have each person in your group get something different and create your own food-sharing feast at the communal tables.
Visit the Eastern State Penitentiary
At one point, Eastern State Penitentiary was the most famous and expensive prison in the world. Today, though, it stands as a crumbling reminder of a prison system that lives on only in our legends and stories of famous criminals like "Slick Willie Sutton and Al Capone. It is also the first of a generation of prisons designed as a true penitentiary ... a detention facility designed to inspire it's residents to become penitent in true regret due to the foreboding architecture and strict discipline.
Book A Philadelphia Tour For Your Guys Weekend
Yo! A Private Rocky Balboa Driving Tour of Philadelphia
Join this exciting “Rocky” movie locations tour and visit several iconic sites that were featured in the legendary franchise. Leave the driving to your local expert guide as you explore the neighborhood that Rocky called home. You'll see his apartment from the first movie, and the building that served as Mighty Mick's Gym. Head down into South Philly, where you can jog up the Italian Market, ask for a blessing at Father Carmine's church and glide past Adrian's Restaurant. Drive out to historic Laurel Hill Cemetery to pay respects to Adrian and Paulie at the headstones that were made for the films. The final highlight will be the famous “Rocky” steps in front of the Philadelphia Museum of Art, where you will also find the giant bronze statue of Rocky himself! Scale the steps for a breathtaking view of the city before striking a pose with the statue for an amazing photo op. Throughout the tour, you and your guide will share Rocky trivia and recite all the quotes word for word.
Philadelphia Phillies Baseball Game at Citizens Bank Park
Philadelphia doesn’t just watch baseball—it lives it. Phillies fans are famously passionate, vocal, and fiercely loyal, creating a home-field energy that’s electric from the first pitch to the final out. At Citizens Bank Park, you're not just a spectator—you’re part of the game. Citizens Bank Park strikes the perfect balance between modern amenities and old-school charm. It’s got wide sightlines, a fan-friendly layout, and excellent food options—including the legendary Philly cheesesteak!. Plus, Ashburn Alley turns a walk around the stadium into a history lesson and local celebration. The Phillies have crafted a roster that blends underdog grit with superstar talent. There’s always drama, energy, and potential for greatness on the field. This is a team that embodies the city’s personality—tough, relentless, and never afraid of a fight. Watching the Phillies live isn’t just about baseball; it’s about tapping into the raw, authentic heart of Philadelphia sports.
Philadelphia Movie and Television Sites Walking Tour
Philadelphia has served as the backdrop for some of your favorite movies and television shows—and there’s no better way to see these famous locations than on this fully guided walking tour. Step behind the scenes of the city’s film history as you explore the streets and landmarks that have appeared on the big and small screen. Along the way, you’ll visit iconic Philadelphia locations like Philadelphia City Hall and LOVE Park, while hearing stories about the filmmakers who brought the city to life on screen, including directors like M. Night Shyamalan and Martin Scorsese. You’ll also stop by filming locations featured in hit shows such as It's Always Sunny in Philadelphia and Cold Case. Of course, no Philadelphia movie tour would be complete without paying tribute to the city’s most famous cinematic hero. You’ll visit several locations from the legendary Rocky franchise—including the world-famous Rocky Steps.
Explore Philadelphia via Vintage Car or Electric cart
Explore the heart of American history and culture with Philly City Tours. Engage in a smooth, fun, and informative journey through Philadelphia, tailored for solo travelers, couples, and families. Experience iconic landmarks while learning about the city’s rich heritage from knowledgeable guides. Perfect for all ages, this tour offers a seamless way to immerse yourself in the vibrant culture of Philadelphia. - Enjoy a guided tour through the historic streets of Philadelphia - Ideal for solo travelers, couples, and families - Knowledgeable guides share fascinating insights about the city - Flexible tour times available throughout the day and night
City Sightseeing Philadelphia HOHO Bus Tour + Bookable Extras
Discover the countless sights Philadelphia has to offer on this thoroughly enjoyable hop-on hop-off bus tour! You'll see all of Philly's iconic landmarks in your own time, including Love Park, Penn's Landing, Philadelphia Zoo and much more! On this 1, 2 or 3 day double-decker tour, you can hop-on and off as many times as you want, or stay on the bus for a full loop. Choose a 1.5 hour Night Tour to experience the dazzling lights of Philadelphia under the starry sky on a Panoramic bus tour. On this tour you can experience Philadelphia's most iconic sights such as Independence Hall, the famous Rocky Steps and Liberty Bell (must be booked separately from the hop-on hop-off bus tour).
Hop-on Hop-off and Philly By Night Tour Combo
Explore the sights and sounds of Philadelphia on board a double-decker, hop-on hop-off bus tour. Visit 27 of the city's top attractions, as a local guide offers live commentary on the points of interest and landmark locations along the way. Popular stops include the Betsy Ross House, the National Constitution Center, the Liberty Bell, Independence Hall, and many more. Then, see the sights illuminated against the evening sky on the guided, 90 minute, 'Philly by Night' bus tour.
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Catch a Game (seriously, Philly Sports are all Awesome!)
While I dream of one day attending a Flyers game, I'd be more than happy to cheer on the Eagles or Phillies too. Oh yeah, and the Sixers are here too. :) Philadelphia is absolutely one of the biggest destinations for sports fans, and win or lose, the fans here are among the fiercest sports fanatics in the US, so it might just be safer to cheer for the home team instead.
Beer Tour
Philadelphia's craft beer scene rivals any major city, with a collection of world-class breweries all within easy reach of downtown. Start at Yards Brewing Company, Philadelphia's largest brewery, where you can tour the facility and sample their revolutionary ales inspired by founding fathers' recipes. From there, hit up Love City Brewing in the Spring Arts district and finish at Philadelphia Brewing Company in Kensington – each offering unique takes on classic styles and innovative new brews in distinctly different neighborhood settings.
If your group has a guy who is not drinking, or you want to do the whole weekend without drinking at all, Philadelphia handles that better than most cities.
McGillin's Olde Ale House
Step into Philadelphia's oldest continuously operating tavern, where the beer has been flowing since 1860 and the walls are literally covered with historical artifacts from the city's past. McGillin's is more than just a bar – it's a living piece of Philly history that serves up excellent pub fare and features 30 beers on tap, including their own McGillin's Real Ale. The place really comes alive on weekend nights with a diverse crowd of locals, students, and visitors all mingling in an atmosphere that perfectly balances historic charm with lively sports bar energy.
Liberty Bell & Independence Hall
No boys' trip to Philadelphia is complete without a quick dive into American history at Independence Hall, where you can actually stand in the room where the Declaration of Independence and U.S. Constitution were debated and signed. While tickets are required during peak season, they're free, and the guided tours last just 30 minutes – perfect for getting your cultural fix without spending the whole day on history. The guides bring the room to life with fascinating stories about the founding fathers' heated debates and power struggles that shaped America.
More Philadelphia Experiences For The Group
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More Ideas For A Philly Guys Getaway!
There's so much to do in Philadelphia that it's sometimes surprising that it's a forgotten city sandwiched between New York and Baltimore/Washington. Today, though, Philly has an amazing food scene, tons of craft beer, and even a handful of distilleries. Here's 10 more ideas for guys looking to plan the ultimate boys trip or guys weekend getaway.
Visit Franklin Institute
One of America's oldest and best science museums, featuring interactive exhibits, an IMAX theater, and a giant walk-through human heart. Perfect for guys who love technology and hands-on experiences.
South Street Bar Crawl
Hit up iconic spots like Tattooed Mom's, Bob & Barbara's (home of the citywide special - a shot and a beer), and Bridget Foy's along this vibrant street known for its eclectic nightlife.
Tour the U.S. Mint
See where America's coins are made and learn about the minting process. It's free and surprisingly fascinating, especially for history or engineering buffs.
Go-Karting at Speed Raceway
Indoor electric karting in nearby Horsham offers high-speed racing on a professional-grade track. Great for adding some adrenaline to the trip.
Penn's Landing Waterfront
Check out seasonal events, concerts, and festivals along the Delaware River waterfront. In winter, there's ice skating; in summer, there are beer gardens and outdoor movies.
Poker Night at Rivers Casino
Try your luck at Philadelphia's waterfront casino, featuring table games, sports betting, and multiple restaurants and bars.
FDR Park Disc Golf
For something more active, this 18-hole disc golf course in South Philly offers a fun outdoor activity, especially if you need some fresh air after too many cheesesteaks.
Schuylkill River Trail Bike Ride
Rent bikes and cruise along the scenic riverside trail, with great skyline views and stops at Boathouse Row. Can be combined with a visit to the Philadelphia Zoo.
Axe Throwing at Urban Axes
Located in Kensington, this BYOB venue offers a unique competitive activity perfect for group entertainment. They provide instruction and run mini-tournaments.
Live Music at Underground Arts
This gritty, industrial-style venue in the Callowhill neighborhood hosts rock shows, comedy nights, and other performances in an authentic Philly atmosphere.
It's a city that's got enough that you can make what you want of it, but don't ignore it when you make plans this year!