Top Massachusetts Dessert Tours

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 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.

Learn about Salem’s mysterious past on this guided walking tour of the city. Follow your historian guide through Salem, listening to 400 years of history, and admire the old architecture that dates back to the early colonial period. Find out the truth about the 1692 Salem Witch Trial hysteria, which has influenced literature and pop culture. For a spookier experience, select the nighttime tour led by lantern light.

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.

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.

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.

For anyone thinking of attending Harvard, or for those who simply want a glimpse of college life at the famous university, this tour is a must. Get an exclusive account from current Harvard students, who provide key insights into the life and times at Cambridge with a theatrical, humorous flair. Check out the old buildings at Harvard Yard and Harvard Square and learn about the school’s storied past. Illustrated map of Harvard Square included. Choose from several departure times throughout the day.

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.

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.

Discover Boston, Salem, and Cape Ann with maximum flexibility using this self-guided audio tour. Location-based narration shares colorful local history as you explore—it’s all at your own pace, which means you can stop and start the guide as you pause to take photos, eat lunch, or take breaks. Since the self-guided tour uses offline maps, it even works without cell service or WiFi.

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.

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.