Top Massachusetts Desserts & Sweets

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.

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.

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.

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.

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.

Combine a historical Cambridge tour with an indulgent chocolate tasting on this engaging walking tour. Pick between afternoon and evening departure times, and meet your guide in the center of Cambridge; with a maximum of 15 attendees, this tour guarantees a personal way to explore. See historical Harvard Square and learn about Harvard University’s history. You’ll also enjoy locally made ice cream, will sip chocolate tea, will browse a traditional candy shop, and much more.

See a different side of Salem, which is well-known for its spooky stories. Instead, you’ll visit some of the city’s candy shops, including the oldest candy shop in the United States, Ye Olde Pepper Companie. Your guide will lead you through town, stopping at highlights and candy shops along the way. Visit places you wouldn’t know about otherwise, and meet fellow sweet-tooths.

Ready to taste Ptown? Lace up for a 2-hour trek through history and coastal rebel lore. You’ll track the footsteps of Anthony Bourdain and dive into the bohemian scene that made this fishing village the birthplace of modern American theater. Find out where the Provincetown Players launched, where an undiscovered Eugene O’Neill staged his first plays. Alongside O'Neill, trailblazing writers like Susan Glaspell, Edna St. Vincent Millay, and John Reed fueled the town's creative fire. Over the decades, icons like Tennessee Williams, Norman Mailer, and poet Mary Oliver drew inspiration from the salt air, while acting legends like Marlon Brando and Bette Davis graced local stages early in their careers.End your journey at Vorelli's Restaurant, a beloved local classic. Sit back, relax, and reward your feet with the ultimate Cape Cod feast: a massive, chunky lobster roll, a rich, creamy cup of New England clam chowder, and a refreshing non-alcoholic beverage of your choice and a ice cream cone

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.

What a way to celebrate the weekend! Enjoy a lovely two hour sail on Boston Harbor with unbeatable views of the city. Your ticket includes complimentary coffee and fresh-baked pastries from the incomparable Flour Bakery + Cafe. Feel free to bring your own food along if you prefer, but please no outside beverages and no coolers. Mimosas are $5 all morning! We also have our full drink menu available including local craft beers, cocktails, wine, soda, juice, and water. We accept Apple Pay, credit cards, or cash onboard.

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.

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.

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.

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.

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.

Have fun and unleash your inner art critic while exploring Central Square, Cambridge with us. Home to a vibrant public art scene, including iconic Graffiti Alley, a sanctioned graffiti walkway that changes daily, and a variety of impressive large scale murals commissioned by the city from award-winning local talent. Uncover the artists and meaning behind these dynamic murals and enjoy delicious, diverse eats from local independent restaurants including gyoza, specialty granola, buddha bowl, oysters, and unique donuts. Guests are invited to try a mocktail or cocktail on this tour, and it is appropriate for all ages. If you’re lucky, you’ll even get a special tour of a hidden passageway. This fun and informative walk will change the way you think about Cambridge. Our friendly and local guides will take guests along Massachusetts Avenue to uncover the evolution of the area and the ever-increasing importance of self expression. Please bring proof of COVID vaccination.