BOSTON · DESSERT TOURS

7 Dessert Walks in Boston Worth Booking

7 tours  ·  from $34

Every trip has one free day too few. These 7 dessert walks justify the slot, priced and timed so you can decide in minutes and get back to the fun part.

Cocktails & Cannoli: Boston's North End Dessert Tour - Starting at 191 Hanover Street
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Cocktails & Cannoli: Boston’s North End Dessert Tour

1.Cocktails & Cannoli: Boston’s North End Dessert Tour

★★★★★★★★★★5.0 · 309 reviews · 2 hours (approx.) Our pick

Walk about 1.5 miles through Boston’s North End with guides such as Pat, Sarah, Deuce, or Gabrielle. You’ll sample four desserts, three cocktails, and a mocktail option when needed, while visiting Paul Revere’s House and Old North Church.

“Tons of fun with tasty drinks and cannoli's. Lots of history and lots of laughs. Deuce (Pat #2) was our guide and he was awesome.”

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Boston: Museum of Ice Cream Entry Ticket - Entering the nine interactive spaces
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Boston: Museum of Ice Cream Entry Ticket

2.Museum of Ice Cream Entry Ticket

★★★★★★★★★★4.2 · 45 reviews · 1h 30m · from $34Best value

Spend about 90 minutes at Boston’s Museum of Ice Cream, an interactive Experium with nine themed spaces, unlimited ice cream, the Sprinkle Pool, and Hall of Freezers. #TeamMOIC guides keep the visit moving, share ice cream facts, and help you enjoy the exhibits safely.

“It didn’t really have any story attached to it. The ice cream was very sweet and sickly. Would recommend for toddlers but nothing older”

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Back Bay Chocolate and Art Galleries Tour - Newbury Street, where the tastings and galleries meet
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Back Bay Chocolate and Art Galleries Tour

3.Back Bay Chocolate and Art Galleries Tour

★★★★★★★★★★5.0 · 29 reviews · 2 hours 30 minutes (approx.) · from $65

Join Adam of Up and Adam Food Tours for a 2.5-hour, 1.3-mile walk through Boston’s Back Bay. You’ll taste hot chocolate, a cookie, cupcake, and chocolate hazelnut cake, visit art galleries, and hear neighborhood history in a group capped at 12.

“Adam was an amazing guide, very very knowledgeable and could answer almost any question you ask. Tasted some of the best chocolatey desserts ever, and saw some beautiful artworks. If you love chocolate and modern art this is the tour for you!”

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Pastries & Prosecco Aboard a Tall Ship in Boston Harbor - Flour pastries make this more than a basic harbor cruise
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Pastries & Prosecco Aboard a Tall Ship in Boston Harbor

4.Pastries & Prosecco Aboard a Tall Ship in Boston Harbor

★★★★★★★★★★5.0 · 14 reviews · 2 hours (approx.) · from $75

Board Liberty Fleet’s traditional tall ship at 11:00 a.m. for a moving two-hour sail around Boston Harbor. Captain Fredo, Jess, and Max lead the onboard experience, with Flour Bakery pastries, coffee, and $5 mimosas available as historic Boston views unfold from the deck.

“Fantastic excursion! Had such a relaxing ride around the harbor. Captain Fredo, Jess and Max made our trip so memorable. Highly recommend this excursion!”

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Harvard Square Chocolate Tour - What you will taste, and why the local focus matters
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Harvard Square Chocolate Tour

5.Harvard Square Chocolate Tour

★★★★★★★★★★4.5 · 14 reviews · 1 hour 30 minutes (approx.) · from $60

Meet your guide in Harvard Square for a 90-minute walking tour linking chocolate tastings with Cambridge history. You will sample sweets, coffee, or tea at local shops, with guides such as Roberta bringing friendly energy to a small group of up to 12 people.

“The chocolate tasting was great, however, I wish more attention was paid to my daughters food allergies.”

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Boston: Back Bay Chocolate and Art Galleries Guided Tour - Italian market cake bites
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Boston: Back Bay Chocolate and Art Galleries Guided Tour

6.Back Bay Chocolate and Art Galleries Guided Tour

★★★★★★★★★★5.0 · 5 reviews · 2h 30m · from $65

Meet Adam at the Prudential Center for a 150-minute guided walk through Back Bay. Taste hot chocolate, cookies, cupcakes, and chocolate hazelnut cake bites, then visit two art galleries and receive Adam’s Boston food and sightseeing tips by email.

“I like the art gallery,. there should be more or at least another art gallery on the tour”

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Back Bay Evening Chocolate Tour - Starting with Back Bay’s architecture and art
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Back Bay Evening Chocolate Tour

7.Back Bay Evening Chocolate Tour

★★★★★★★★★★5.0 · 4 reviews · from $60

Join guide Adam from UpandAdam for a two-hour walk through Boston’s Back Bay, with hot chocolate, a cookie, cupcake, and chocolate hazelnut cake. You’ll visit two art galleries, stroll Newbury Street and Commonwealth Avenue, and finish about half a mile from the start.

“Adam from UpandAdam yours was a great host, very knowledgeable. He made the tour interesting and personalized, since I was the only person who signed up!”

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