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The 9 best Boston walking tours

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

Gerrish Lopez
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Here's one for the history buffs. Boston is famous throughout America – and abroad – for its rich role in the nation’s history. Understandably, the city is dotted with one-of-a-kind landmarks, including Charleston Navy Yard and the unmissable Freedom Trail (made up of no less than 16 iconic locations). And the best way to see many of these showstopper spots is on your own two feet.

So slip on some comfy footwear and make a booking with a local expert who will make every minute of your time in Boston count. And, ff 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. Guided Delicious Donut Tour

Foodie fact: New England is the donut capital of the United States. And Boston seizes this crown with style and force. Explore four of the city’s best donut makers on a tour that ensures nobody ends up walking about on an empty stomach. You’ll get to sample the culinary creativity of Bostonian bakers with flavours ranging from city-specific classics to quirky contemporary newbies. Wash it all down with a strong coffee and/or a cup of cider.

Don’t miss: It’s not all about the donuts (just… almost). You’ll also enjoy a curated history tour featuring some of the city’s most unique sites.

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5. 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. 

6. Boston Fenway Park Guided Tours

Boston: it’s all about the history – right? Well for some, that doesn’t mean the stuff inside the museums or inscribed on monuments, it means the history of the Red Sox. Brush up your knowledge of this world-famous baseball team with stadium tours that come in four different shapes and sizes. You’ll get a behind-the-scenes Fenway Park experience that’s been known to entertain even those who swear they don’t like baseball – honestly.

Don’t miss: Proper fans will want to book the pre-game tour to help them get into the spirt of things before also seeing a match. Just remember to book your match tickets separately.

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7. Ghosts and Gravestone Tour

With all the h.i.s.t.o.r.y floating around town, it is any surprise that Boston also has its own collection of spooks and spectres? This 90 minute tour takes in two of the city’s most ghostly burial grounds, featuring famous names and good honest Bostonians from across the decades. Get to know some of the scarier stories (including the Boston Strangler) and the most unusual cast of characters.

Don’t miss: Your guide will be none other than a 17th century gravedigger.

8. Women’s Rights in Back Bay

Get an alternative view of Boston’s past with a tour that focuses in on the fight for women’s suffrage. Starting on Boston Common, the tour trots off to Back Bay – with all its excellent surprises – while telling you the story of 1870 – 1920, when American women fought for the right to cast a ballot. It’s a great chance to really feel history come alive and to align the stories with the physical characteristics of the city today.

Don’t miss: Marvel at the gorgeous Victorian era architecture found in this area of the city.

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9. 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. 

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