Recently voted as one of TripAdvisor's top food tours in the US. 

Explore Boston's sweetest side on the Underground Donut Tour, a delicious journey through the city's most iconic neighborhoods and bakeries. We'll kick things off downtown at Kane's Donuts in the Financial District, sampling some of their classic creations before strolling along the harbor and through historic Quincy Market. From there, we'll head to the Boston Public Market for warm, fresh cider donuts that capture the flavors of New England. Next, we'll taste a selection of artisanal donuts made fresh daily by local bakers before making our way to the North End, Boston's beloved Italian district. Our final stop is the legendary Bova's Bakery, where we'll finish with a specialty Boston donut that's worth every bite. Come hungry, this walking tour is a perfect blend of history, culture, and irresistible flavor.

Delicious Donuts of Boston: A Sweet History Walking Tour

BUT FIRST, DESSERT!

Do dessert before dinner when you join us for Cocktails & Cannoli, an all inclusive walking food tour of Boston's North End.

Skip the infamous lines to taste delicious drinks and classic cannoli, and sample the best sweets the North End has to offer. Not to mention the Paul Revere House and Old North Church along the way!

To top it all off, our local tour guides will sprinkle in fascinating historic knowledge, fun cultural facts, and culinary tidbits.

Cocktails & Cannoli: Boston's North End Dessert Tour

Welcome to the North End Bakery & Cafe Tour! Join the group and skip the lines as we have tastings from three bakeries and one cafe and venture through one of Boston's oldest and most important neighborhoods. Home to roughly 95 restaurants and 3 stops on Boston's Freedom Trail, you'll never run out of things to learn and places to try here.

During this tour, we'll taste the following:

-Sfogliatella from an underground bakery in a tucked-away alley
-Tiramisu from the oldest Italian café in Boston
-Florentine cannoli from a 24/7 bakery that's been a North End institution since 1926
-Chocolate ganache from a family-owned bakery that's been on Hanover St since 1930

And as a parting gift for joining the tour, you will be sent a post-tour email covering more of my favorite places to go, things to do, and food & drink to enjoy while you're in the Boston area!

Tastings are subject to change. Please alert us of any dietary restrictions or allergies before booking.

North End Bakery & Cafe Tour

Boston's North End is the city's oldest residential neighborhood and one of its most vibrant. Over time it transformed into Boston's beloved "Little Italy," thanks to Italian immigrants who filled its narrow streets with food, family traditions, and unforgettable flavor.

The best way to experience this historic neighborhood is with your taste buds. On this food tour, you'll stroll through the North End's cobblestone streets while sampling local favorites—from rich Italian coffee to piping-hot pizza.

You'll even take part in Boston's sweetest rivalry with tastings from Modern Pastry and Mike's Pastry, deciding for yourself who truly serves the best cannoli.

Along the way, you'll also hear stories of famous residents like Paul Revere and boxing champion Tony DeMarco who once walked these same historic streets.

2 Hour North End 'Little Italy' Walking Tour

This small-group tour stands out by offering an intimate, authentic experience, allowing guests to connect more deeply with Boston's local stories. With a focus on personal attention, our passionate local guides share not just historical facts but real, untold stories of the city, making each stop feel unique. The small group size ensures a more personalized experience, giving you the chance to ask questions, interact, and truly immerse yourself in the heart of Boston's history. It's more than just a tour—it's a genuine journey through the city's past, told by the people who live it.

Freedom Trail and North End History and Culinary Delights

Boston's story didn't end with the American Revolution—it only got more delicious. Shaped by waves of immigration, global trade, and constant innovation, Boston and its food have evolved. Every bite tells a piece of the city's history, even some we're not proud of.

Food reflects who we are—your culture, your environment, and your economy—and in Boston, that spans centuries of change.

On this walking tour, you'll explore Boston's rich history through the lens of what its people have harvested, eaten, and produced—from pre-Colonial Native Americans to the 20th century. Discover how molasses fueled candy and commerce, cod fed empires, science expanded diets, and tea sparked revolution.

We'll taste classic New England dishes and modern Boston favorites, plus some sweet surprises you might not realize have local roots!

If you're hungry to go beyond the Freedom Trail and experience Boston's history through its flavors, this tour is for you. Bring your appetite and your walking shoes.

Dessert Tours in Boston

Delicious Donuts of Boston: A Sweet History Walking Tour

Cocktails & Cannoli: Boston's North End Dessert Tour

North End Bakery & Cafe Tour

2 Hour North End 'Little Italy' Walking Tour

Freedom Trail and North End History and Culinary Delights

Cod, Tea and Candy a Boston Food History Walking Tour