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The 9 best Boston walking tours

See the city on foot with these fun and informative walking tours around Boston

Contributor: Talia Stanton
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Boston is a city that's played a significant role in American history for centuries, and has hundreds of landmarks to prove it. There's so much to learn, see and do; from traversing the iconic Freedom Trail, taking you across 16 historic sites, to discovering the maritime hub of Charlestown Navy Yard. Boston's compact layout and walkability makes it easy to explore of foot, and that's where Boston's best walking tours come in...

Soak up the culture and learn all about the city's most famous attractions with the assistance of an all-knowing guide who's determined to help you make the most of your time in Boston. If you're more into eating than sightseeing, get to know the city's rich culinary scene with a food tour that will steer you towards the best of the best. And once youve finished a tour, keep the fun going by checking out the best museums in Boston or hitting up some of the top bars

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Best Boston walking tours

1. Freedom Trail Walking Tour

This 90-minute tour will take you on a history lesson in America's revolutionary founding across the Boston Freedom Trail's famous red line. From Boston Common to the final resting place of Paul Revere, you'll be walking in the footsteps of patriots and hearing tales of their bravery. Eleven of the sixteen official Freedom Trail sites are featured on the tour. 

Don't miss: Taking a ride on the Swan Boats in the Boston Public Garden after the tour; they've been operating for over 140 years and offer the best views of the gardens. 

2. 2-Hour Historic Walking Tour

This is one for those who want to explore the city in detail; this lengthy tour covers the city's most historic neighborhoods, from Breacon Hill to the Back Bay and Copley Square. You'll get to see the 19th-century architecture in all its glory walk around the residential streets. The small-group set-up allows for interactions with the guide and means you'll be able to hear all the wisdom they impart loud and clear. 

Don't miss: The many important sites such as Faneuil Hall, the Old South Meeting House, the Old and New State Houses and the Old Corner Bookstore.

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3. Mobsters, Mayhem and Murder Walking Tour

Delve into the history of of Boston's most famous organized crime figures on this sinister walking tour. Local guides will be providing the inside scoop on the criminal underworld, reciting stories of notorious mobsters like James 'Whitey' Bulger and other tales of violence and law breaking. 

Don't miss: A lesson in pirate history as you walk along the harbor, before entering Boston's own Little Italy: the North End. 

4. Boston Movie Mile

Movie fans can visit a tonne of filming locations from movies and TV on this tour—which is led by a local actor. From benches (Ted and Good Will Hunting) and bars (Cheers and The Departed) to the street of the famous car crash in Blown Away, you can reenact movie scenes while also learning about some of Boston’s historic landmarks. This one often sells out, so book in advance. 

Don't miss: Listening in on some behind-the-scenes info about Boston’s film industry. 

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5. Secret North End Food Tour

For a unique, food-focused adventure, check out this 3-hour walking tour of North End. Enjoy fresh seafood along with some of the most famous Italian food in the neighborhood, before trying one of the city's best cannolis. 

Don't miss: Uncovering the secrets of the Boston Public Market and learning how to bypass the long lines for the best lobster roll in town. 

6. PhotoWalks Highlights of Boston

For photo enthusiasts and Instagram influencers, PhotoWalks offers walking tours through Boston landmarks and give instructions and creative tips on how to best capture them, whether with a digital SLR or just a smartphone. The highlights of this Boston tour cover the most photogenic parts of the Freedom Trail, Beacon Hill, the Public Garden, and Back Bay's beautiful 19th-century residential neighborhood. 

Don't miss: The fascinating commentary of Boston's most iconic landmarks. 

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7. Boston Historic Taverns Tasting Tour

Beers and bar snacks sure do make a history lesson a whole lot more funand this tour is here to prove it. You’ll visit a series of historic taverns ont his guided bar crawl. Explore Blackstone Block, the North End, and more of the city's oldest neighborhoods. You'll then also get to embark on a scenic ferry ride once you'd had enough cold ones. 

Don't miss: A visit to the oldest tavern in America, which first opened in 1795. 

8. PhotoWalks Beacon Hill Tour

Beacon Hill is one of the most exclusive residential areas in Boston. The neighborhood’s narrow streets, 19th-century homes, charming architectural details, brick sidewalks, gas lamps, and colorful flowers make it one of the most photographed segments in the city. To make sure you capture the beauty of this area, while also learning about its fascinating history, take a PhotoWalks tour led by a professional photographer.

Dont miss: Picking up creative photography tips and a lesson in how to capture the beauty of a scene from unexpected angles. 

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9. Harvard Campus Walking Tour

You might just soak up some smarts on this Trademark Tours Harvard Campus Walking Tour. Current Harvard students will guide you around the campus and share their experiences. Visit historic buildings in Harvard Yard, see the famous John Harvard Statue, explore the surrounding Harvard Square neighborhood, and hear stories about some of the famous people who attended the school. 

Don't miss: Getting your hands on an illistrated map of Harvard Square. 

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