M. Fischetti for VISIT PHILADELPHIA™

Five tours of Philadelphia that go deeper into the City of Brotherly Love.

September 28, 2015

Consistently ranked as one of the country’s most walkable cities, Philadelphia is ripe with colorful neighborhoods, great buildings, and cultural sites to explore. No better way to enjoy it, then, than on an immersive walking tour that dives deep into the city’s impressive history, or gives you a taste of its wide culinary flavors. We’ve picked five of our favorites tours that give you the best Philadelphia has to offer.

Constitutional Walking Tour

First-time visitors to Philadelphia should beeline for the city’s array of historic sites. On a 1.25-mile stroll, the Constitutional Walking Tour (from $19) manages to capture more than 20 of the most important ones in American history. Major stop include Independence Hall, the Liberty Bell, and the Constitution Center, while lesser-known buildings, homes, and parks pad the educational experience. Carpenters’ Hall, for example, is where the First Continental Congress met in 1774. Also on the itinerary: the cemetery where Ben Franklin is buried, the Betsy Ross House, and the first and second Banks of the United States.

Grim Philly Twilight Tours

It’s adults only on the Grim Philly Twilight Tours (from $20), where brave souls hear tales from Philly’s dark past. Developed by a university professor, guides tell well-researched stories of serial killers, vampires, aphrodisiacs, ghost hunting, grave robbing, gangsters, and pirates. Each of their nine itineraries focuses on specific subjects and drinking tours are on offer. Walking is minimal on all, and includes opportunities for sitting.

Related: Best Walking Shoes for Women

Italian Market Immersion

Seemingly a world away from Philadelphia’s colonial sites, the South Philly section has a rich history of its own. The Italian Market Immersion ($25) explores this neighborhood through its food. Cheese, chocolate, spice, and olive oil stands abound at the famous outdoor market, which is open daily and is America’s largest. Along the way, you’ll hear stories from owners and employees at the shops and stalls. The tour ends at the intersection of Philly’s two most famous cheesesteak shops, Pat’s and Geno’s.

Architectural Walking Tours with the Preservation Alliance

Philadelphia is home to a rich variety of architectural styles, including French Second Empire, Italian Renaissance, Art Deco, Late Victorian, Beaux Arts, Georgian, Federal and Greek Revival. Three days a week, the Preservation Alliance for Greater Philadelphia offers a robust line-up of walking tours—65 in total—of Philadelphia and its suburbs. These experiences are an ideal way to explore the many neighborhoods in and around Center City ($15).

Real Philadelphia Tour

Locals and insiders contributed to creating the itinerary on the Real Philadelphia Tour. In less than four-and-a-half hours, you’ll walk a 5K with stops at City Hall, some of Philly’s many murals, LOVE Park, the Avenue of the Arts, Chinatown, funky South Street, the Italian Market for lunch, the Reading Terminal Market, and Magic Gardens—a world of mosaic tile and recycled items occupying half a city block. The tour is pay-what-you-wish and reservations are required.

Sarah Maiellano is on the Philadelphia beat for Travel + Leisure. You can follow her on Twitter at @SarahMaiellano.

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