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10 Insanely Fun Food & Drinking Outings of Boston in 2023

Boston is a fantastic city with a rich history and is famously recognized globally as the birthplace of the American revolution. Alongside this, it is also known as a city of fantastic culture, food, and drink. 

With the return of group activities in Summer 2021 post-Covid, there’s no better way to see and experience all the history Boston has to offer than by taking a walking tour. We’ve put together 10 of the best historical food and drink walking tours below so that you can satisfy all your cravings while experiencing Boston’s rich history in a way you’ve never done so before! Your group is guaranteed to love it. 



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  1. Boston Walking Food Tour

a statue in front of a building


Boston is the city central to the American Revolution, and the birthplace of the nation. This amazing walking tour combines the dramatic history of the city with all the delicious food and drink it has to offer. 

Sample food from our favorite establishments and learn tidbits about how they came about. 



Our Recommendation 

  1. Boston Cooking Class

a close up of a person cutting a piece of broccoli

Fresh ingredients, loads of flavor, professional chefs


Do you want to learn something new? Whether you’re a waffle in the toaster breakfast maker or a ricotta lemon pancake extraordinaire, you will learn something to take home with you at our incredible cooking classes in Boston! 

Our professional chefs lead your through a recipe, teaching you techniques and using fresh ingredients.

  1. Historic Taverns and Pizza Tour

History and Food Tour featuring Pizza

Boston is home to many historic taverns, often rallying points for local patriots to fight with colonial rulers, and likely where the first seeds of the Revolution were sown. This is a fantastic tour, featuring several historic landmarks, and fantastic pizza that Boston has to offer. You won’t want to miss out, so book soon to to reserve your spot!

  1. Historic Pub Crawl Tour Along the Freedom Trail

The Freedom Trail Boston Plaque

Combine two things Boston does best in this tour: amazing history, and delicious beer! This historic tour focuses on some of Boston’s oldest downtown pubs that are favorites amongst the locals and introduces you to Boston’s nightlife from the point of view of a local. The tour lasts about 2 and a half hours and is a fantastic way to both explore the city, and get your beer fix for the evening. 

  1. Independence Pub Crawl

Boston Old City Hall

For those with limited time on their hands, but still keen to experience Boston’s many vibrant pubs and watering holes, the Independence Pub Crawl is a fantastic tour option. The tour is led by a local spirt enthusiast and history expert, who will be sure to provide all the insider knowledge on the city’s historic venues and give you the opportunity to sample the city’s microbrews and ciders beloved by locals. Book today for an unforgettable night out! 

  1. South End Wine and Walking Tour

Pouring Wine on a Wine Tour

Boston’s South End neighborhood is one of the city’s most famous and recognizable locations, due to being featured in many popular movies over the years. Experience this part of town for yourself, and try the surprisingly international cuisine on offer. You’ll enjoy the stunning architecture of the South End while discovering all the amazing and unique restaurants of the area. Don’t miss out!

  1. Boston’s North End Pizza and Cannoli Small-Group History Walking Tour

Food Tour featuring Cannoli

If you’ve got a specific craving for Italian food, this is the walking tour for you. This tour focuses on Boston’s little Italy within the North End of the city, which is home to over 50 different pizzerias! The stops on this tour rotate but include a range of different pizza types, from Neopolitan to Sicilian. Best of all, every tour ends with delicious cannoli from a North End bakery! 

  1. Boston’s Historic Taverns Guiding Walking Tour Plus Boston Harbour Ferry Ride

Boston Harbour and USS Constitution

If you’re looking to combine a walking tour with a little something extra, why not try this historic taverns tour, with the added bonus of a ferry ride in the harbor? Get up close and personal with where the American Revolution all began, alongside sampling some of the best wines and beers on offer in Boston. 

  1. Cocoa Beantown: Boston’s Premier Chocolate Tour

Food Tour featuring Chocolate

If you’ve got a sweet tooth, then this undoubtedly the tour for you! Alongside picnic tours, Cocoa Beantown is back for private walking tour bookings, making it a great opportunity for a special, customized day out. Each tour lasts around 2.5 hours and is suitable for the entire family. Learn about Boston’s history, and discover the best local spots and the most delicious chocolate! 

  1. Sip of Boston Brewery Tour

Brewery Tour

Boston is home to many famous beer brands, but of them all, Samuel Adams is the most well-known and renowned in the area. On this tour, you’ll get the opportunity to visit the brewing facilities and learn all about Boston’s historic and thriving culture of beers, brewing, and distilleries! 

The tour includes 12 beer samples, a local hand-rolled pretzel snack, and round trip transportation, making it fantastic value for money, and something that beer and history fanatics alike will love. Book today to avoid disappointment!