Top Massachusetts Street Food Tours

While Boston is home to lots of different food tours, not many let you eat like a local on a trip around an Italian neighborhood filled with mom-and-pop shops. On this half-day guided culinary tour, enjoy rich coffee, cheesy pizza, loaded Italian subs, and much more as you explore Boston’s North End.

Dive into the historic grit and gourmet soul of the "Cradle of Liberty". We’ll bypass the typical tourist traps to explore the city’s oldest corridors, shifting from the maritime majesty of the waterfront to the legendary cobblestone streets of the North End. The journey begins at the iconic Quincy Market, the crown jewel of the city’s 19th-century urban renewal. Standing beneath its massive copper dome, you’ll discover the market's transformation from a wholesale meat center to a world-class gathering spot. As we cross into the North End, the aroma of roasted garlic and fresh bread signals your arrival in Boston’s oldest residential neighborhood. We conclude your adventure at the Boston Public Market, a vibrant indoor hub that celebrates the rugged spirit of New England’s farmers. Surrounded by stalls of fresh Atlantic seafood and artisan crafts, we’ll gather for your Secret Dish, a savory specialty that captures the essence of Massachusetts heritage.

Explore the cobblestone streets of Boston’s North End and taste your way through the neighborhood with this private food tour. Meet your guide for a half-day tour that includes some of the city’s best Italian food and go off-the-beaten-path to see where locals shop for quality ingredients. Learn about the neighborhood from a local guide while sampling its many flavors.

Don’t waste time looking for the ideal place to eat as you walk the cobblestone streets of Boston’s North End. Join other passionate foodies to snack your way through the neighborhood’s hidden gems. Your guide directs you to a hidden Italian bakery, an authentic Italian salumeria, and a family-run pastry shop. Visit the Old North Church (or equivalent alternative) and enjoy a rich cappuccino or bold espresso with a pastry.

Discover some of Boston's most notable historic landmarks—and pair your sightseeing with a pizza crawl—on this time-saving, two-in-one walking tour. With just a guide and small group for company, stroll through the city’s oldest neighborhoods, including Little Italy on the North End. Walk along the Freedom Trail to sights including Paul Revere House and the USS Constitution, and head to local pizzerias for three full-size slices along the way.

Experience the best of East Coast cities experience that includes three exciting destinations filled with food tours, history walks, and authentic local experiences! With local experts to lead the way, you’ll discover incredible seafood in Boston, visit top historic attractions of Philadelphia and indulge in the world-famous cheesesteak, and enjoy both the culinary scenes of country and city from Amish towns to the Big Apple! During our 7-day tour, you’ll enjoy time with a knowledgeable guide as well as time for yourself to enjoy shopping, exploring, and more good eatin’. History lovers will enjoy the charm of Philadelphia’s Old City and symbols of the American Revolution from the Liberty Bell to Independence Hall. Foodies will fall for Boston’s unbeatable culinary scene, from its lobster to its clam “chowdah”. So leave the driving to us, come hungry, and get ready for an unforgettable East Coast food lover’s adventure!

Combine two attractions Boston has to offer—delicious food and rich history—on this walking tour that starts in the popular North End and continues along the Freedom Trail. Taste fresh bread, pizza, and a classic Italian deli sandwich at local stops in this historic Italian neighborhood. Then, walk the Freedom Trail to learn about the American Revolution, all while enjoying scenic views of Boston Harbor and the Rose Kennedy Greenway. Explore the charming architecture of Beacon Hill and experience the city's blend of old and new.

Taste your way through Union Square, Somerville with this neighborhood food tour. Discover the area that saw the creation of marshmallow fluff and the raising of the first American flag. Walk the streets and stop for delicious tastings at five or six restaurants. Sample a range of local favorites and ethnic delicacies. This tour is suitable for all ages, with alcohol available to guests 21 and over.

Embark on a foodie adventure in Cambridge’s Harvard Square—and head to local spots you might miss if you were on your own—on this small-group walking tour. Follow your guide around the vibrant area near Harvard University, which offers diverse tastings from Greek food to Latin cuisine. Visit an underground tavern, pizza shop, and several other restaurants, and learn insider stories about the area's food history and culture from your guide.

Boston is famous for its donuts and has numerous artisanal donut stores, some hidden away from its tourist areas. Instead of hunting them down independently, let a guide lead you there and introduce you to some top donut varieties, enabling you to try flavors and gain insight into the local donut scene you might otherwise miss. Between tastings, browse a market, eat a delicious bakery treat and explore historical neighborhoods such as North End before one final, scrumptious donut sampling.

Satisfy your cravings on the Original Harvard Square Donut Tour, where you’ll taste the best donuts in Boston at FOUR unique stops. This delightful 90-minute journey takes you through the historic Harvard Square, sampling a variety of donut styles—from savory to churros and everything in between. We even pair the donuts with authentic greek coffee! Enjoy fun stories about the area and the treats you’ll indulge in, making it a perfect outing for families, teens, and donut lovers alike. - 90-minute tour featuring 4 delicious stops in Harvard Square - Sample unique donuts including savory, sweet, churros, and Greek loukoumades - Enjoy a greek coffee or lemonade pairing with your treats - Fun for all ages with intriguing tales of Harvard Square history and donuts!

Your holiday tour begins in the Financial District at Kane’s Donuts where we’ll sample several of their daily flavors. After which, we’ll take a leisurely stroll along the waterfront on the way over to Boston’s Public Market. While there, we’ll try some delicious donuts and apple cider. You’ll also learn some history around the market and have a moment to check out other vendors. On to the third stop, we’ll walk through Boston’s North End neighborhood. It’s also the home to the Old North Church, which was the starting point for Paul Revere’s famous ride during the Revolutionary War. In the North End, we’ll stop at one of the oldest bakeries in the neighborhood. We’ll have a uniquely Boston treat while we’re here. Lastly, we’ll walk back through the North End to end the tour back at the Public Market where we’ll finish with Union Square Donuts. We’re so excited to share this experience and the amazing donuts of Boston. We hope you can join us very soon!