Planning a long weekend getaway to the City of Brotherly Love? Few destinations are as packed with history, culture, and incredible food as Philadelphia. As the birthplace of America, Philly offers iconic landmarks like Independence Hall and the Liberty Bell alongside vibrant neighborhoods, world-class museums, and a booming culinary scene. Whether you’re a history buff, an art lover, or a foodie craving an authentic Philly cheesesteak, this itinerary will guide you through the best ways to experience Philadelphia in just three days. You’ll leave with a deep appreciation for the city – and probably a full stomach! From exploring charming cobblestone streets to cruising along the Delaware River with City Cruises, here’s how to make the most of your Philly adventure.
Day 1: Dive into Philadelphia’s History & Classic Eats
Morning: Independence National Historical Park
Start your Philly adventure in the heart of American history at Independence National Historical Park, where the foundations of the United States were laid. Begin at Independence Hall, the legendary site where both the Declaration of Independence and the U.S. Constitution were signed, shaping the nation’s future. Just across the street, stop by the Liberty Bell, one of the most enduring symbols of American freedom. For a deeper dive into the country’s revolutionary past, visit the Museum of the American Revolution, where interactive exhibits bring the struggles and triumphs of the era to life.
Afternoon: Refuel with a Delicious Lunch on the Delaware River
Our Philadelphia Signature Lunch Cruise is an unforgettable, 2-hour afternoon experience for those looking for some daytime fun. Enjoy a delicious, chef-prepared buffet and gorgeous views of Philadelphia’s spectacular skyline and architecture. From our cozy, climate-controlled interior and open-air decks, you’ll marvel at famed city landmarks like the Ben Franklin Bridge. Don’t forget to visit the fully stocked bar for creative cocktails, beer, and wine – to go with deck games, and lively music from our DJ.
Late Afternoon: Wander One of America’s Historic Neighborhoods
Exploring Old City in Philadelphia is like walking through history, with its charming cobblestone streets and iconic landmarks. A must-see is Elfreth’s Alley, the oldest continuously inhabited residential street in the U.S., offering a glimpse into 18th-century life. History lovers can visit the Betsy Ross House, where the legendary seamstress is said to have sewn the first American flag. Just a short walk away, Christ Church & Burial Ground serves as the final resting place of Benjamin Franklin, who many consider one of America’s Founding Fathers. Along with its historic sites, Old City is also home to vibrant art galleries, boutique shops, and fantastic restaurants, making it the perfect place to experience Philadelphia’s past and present.
Evening: Sunset at Spruce Street Harbor Park or Penn’s Landing
End your first day in Philadelphia with a relaxing evening at Penn’s Landing, a scenic waterfront destination offering year-round entertainment. During the warmer months, head to Spruce Street Harbor Park, where you can unwind in colorful hammocks, stroll along floating gardens, and enjoy delicious bites from local food stalls. Grab a craft beer or a tasty snack while taking in the beautiful views of the Delaware River. If you’re visiting in the winter, don’t miss Blue Cross RiverRink Winterfest, where you can lace up your skates for a fun ice-skating session or cozy up in a charming cabin with hot chocolate.
Day 2: Explore Philadelphia’s Museums, Art, and Culture
Morning: Bring on the Day with a Beautiful Brunch Cruise
What better way to start your day than with a beautiful brunch on the water? Book our Philadelphia Signature Brunch Cruise for a delicious and exciting experience on the Delaware River. Get ready to dine and dance with views of the city’s magnificent skyline. Enjoy a mouthwatering, chef-prepared buffet, paired with spectacular vistas of Philly’s iconic landmarks and downtown skyline. We keep the spirits flowing with a fully stocked bar featuring unlimited mimosas, games, and lively music from our onboard DJ. Join us for a memorable, one-of-a-kind brunch cruise on the water!
Afternoon: Philadelphia Museums and Lunch at Reading Terminal Market
Spend your afternoon in Philadelphia exploring some of its most iconic spots. Start by climbing the famous Rocky Steps at the Philadelphia Museum of Art, where you can snap a photo with the Rocky Statue before heading inside to admire an impressive collection of artwork from renowned artists like Van Gogh and Picasso. After soaking in some culture, make your way to Reading Terminal Market, one of the oldest and most famous food markets in the U.S. Grab a DiNic’s Roast Pork Sandwich, a Philly favorite, or 
sample Amish baked goods and a sweet treat from Beiler’s Donuts and Pickle Patch. With diverse food options, including Middle Eastern, Italian, and Cajun cuisine, there’s something for every palate.
For the rest of the afternoon, choose between two exciting attractions: visit The Franklin Institute for an interactive, hands-on science experience perfect for all ages or explore the vibrant and immersive art world of Philadelphia’s Magic Gardens, a stunning mosaic-covered space created by artist Isaiah Zagar. No matter what you choose, this afternoon’s itinerary offers the perfect mix of culture, food, and creativity in the heart of Philly.
Evening: Dinner & Nightlife in Rittenhouse Square
Enjoy your evening in Rittenhouse Square, one of Philadelphia’s most upscale and vibrant neighborhoods. Start with an unforgettable fine dining experience at Vernick Food & Drink, known for its expertly crafted dishes, or indulge in Mediterranean-inspired small plates at Barbuzzo. After dinner, if you’re in the mood for cocktails, head to The Ranstead Room, a hidden speakeasy with a cozy, intimate vibe and expertly mixed drinks. For a more relaxed way to end the night, take a leisurely stroll through Rittenhouse Square Park, where you can enjoy the beautifully lit pathways and charming atmosphere.
Day 3: Local Vibes & Outdoor Adventures in Philly
Morning: Philadelphia’s Fairmount Park
Kick off your final day with a visit to one of the largest urban parks in the country, Fairmount Park. It offers miles of scenic trails, picturesque waterfront views along the Schuylkill River, and lush green spaces perfect for picnicking and relaxing. Visitors can explore historic landmarks like Shofuso Japanese House and Garden, admire public art, or tour grand 18th-century mansions nestled within the park. There are plenty of outdoor activities, too, from hiking and biking to rowing and even exploring Boathouse Row, a picturesque and historic area along the river.
Afternoon: Eastern State Penitentiary and Philly Cheesesteaks
For a fascinating (and slightly eerie) experience, visit Eastern State Penitentiary, once home to notorious criminals like Al Capone. You’ll learn about the history of the U.S. prison system and walk through creepy cellblocks. According to the penitentiary’s website, “Eastern State Penitentiary was once the most famous and expensive prison in the world, but stands today in ruin, a haunting world of crumbling cellblocks and empty guard towers.” If you are visiting in October, check out Halloween Nights, a famous haunted house attraction.
You can’t visit Philadelphia without trying its most famous dish – the cheesesteak! Two of the most famous spots are Pat’s King of Steaks – the inventor of the cheesesteak- and Geno’s Steaks – Pat’s longtime rival, serving up a slightly different take. Our suggestion: try both!
Evening: Sunset on the Water with City Cruises
End your trip with a fantastic experience on the water, offering the perfect setting to catch a stunning sunset. For a special night in Philly, dine, dance, and take in the fantastic views of the city’s skyline on our Philadelphia Signature Dinner Cruise. Departing from Penn’s Landing, our 2.5- to 3-hour dinner cruise on the Delaware River lets you relax and enjoy the beauty of Philly’s historic waterfront. You’ll savor freshly prepared entrees, salads, and desserts. Hit the bar for creative cocktails, wine, and beer, and dance the night under the stars thanks to our live DJ entertainment. Whether you’re looking for a romantic night on the water or the company of old friends, an evening dinner cruise is one you’re sure to remember!
Make City Cruises Part of Your 3-Day Adventure in Philadelphia
After three incredible days in Philadelphia, you’ll leave with a newfound deep appreciation for a truly underrated destination. From strolling through historic neighborhoods and exploring iconic landmarks to indulging in delicious food scene cheesesteaks, the City of Brotherly Love has something for everyone. And to top it all off, a City Cruises experience on the Delaware River offers the perfect way to soak in breathtaking skyline views, enjoy a memorable meal, or celebrate a special occasion on the water. Whether sightseeing, dining, or simply unwinding as the city lights reflect on the water, City Cruises adds an unforgettable touch to any 3-day Philadelphia getaway.