Top Boston Desserts & Sweets in 2026

Explore Boston’s North End through its food on a guided walking tour that blends local history with tastings at long-established eateries. This experience offers insight into the neighborhood’s Italian-American roots while helping you navigate its most respected food spots without guesswork. With curated stops and storytelling throughout, it’s an efficient way to understand the area’s culture, avoid tourist traps, and sample classic flavors in a short time.

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.

The Museum of Ice Cream is a self-guided interactive ice cream museum in Boston’s Seaport District and a must-see attraction for families, couples, and friends. The experience invites visitors to play, explore, and dive into the world-famous Sprinkle Pool. If you’re searching for an immersive experience that’s equal parts playful and unforgettable, you’ve found the perfect place – a vibrant oasis of creativity and sweetness.

Not many tours combine an exploration of art and architecture with chocolate tastings. On this small-group tour, head to Back Bay to explore the district’s diverse 19th and 20th-century architecture. Stop at several different chocolate vendors and bakeries, interspersed with visits to two different art galleries across the neighborhood, including one featuring 56 artists with ceramics, paintings, and mobiles.

There’s more to Boston’s neighborhood of Little Italy than good cannoli (though you will make two stops for good cannoli). Get to know the city’s North End in a tour that blends local history with a food crawl. From handmade pasta to fresh coffee, sample several local specialties in the time it would take you to have a single meal. Come hungry and ready to walk around.

Welcome to the Boston Seafood Tour! I created a guided culinary experience featuring New England seafood classics, many of which date back hundreds of years. We'll explore the waterfront, one of the city's best indoor markets, and the North End, known for its multi-generational Italian American culture and abundance of seafood, markets, bakeries, and cafes. During this tour, we'll taste the following: -Clam chowder from one of the essential Boston Waterfront restaurants -Clams casino from an over 50-year-old family-run institution -Lobster rolls inside a year-round marketplace featuring over 30 New England artisans and food producers -Fried scallops from a Sicilian-inspired grab-and-go seafood vendor on Hanover St -Mini cannoli from one of the Big 3 bakeries in the North End As a parting gift for joining the tour, you will receive a post-tour email highlighting my favorite places to visit, activities to enjoy, and local food & drink options.

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.

Taste only the best in Boston’s North End. This foodie tour takes you to a careful selection of award-winning restaurants throughout this historic neighborhood. Stop by Best of Boston winners to sample the city’s top pizza, sandwiches, and bread. Sample iconic cannoli and visit an Old World salumeria shown on the Food Network. Learn about Boston’s rich culinary history, and and end your tour with a delicious pasta finale.

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.

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.