7 Dessert Tours in Boston for a Spare Boston Afternoon

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 a local guide such as Pat, Sarah, Gabrielle, or Deuce. Expect four dessert samples, including cannoli and gelato, three cocktail samples, a blind cannoli taste-off, and stops near Paul Revere’s House and Old North Church. The tour lasts about two to two and a half hours and is for ages 21 and up.

“We loved this tour! Pat was a fantastic guide and took us to really cool places we would never have seen otherwise. The cocktails were all delicious, and bonus my husband wasn’t drinking this trip so he had a mocktail at every stop! Thanks Pat for doing that! The desserts were also amazing. What a great way to spend time in the North End.”

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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, moving at your own pace through nine interactive spaces, including the Sprinkle Pool and Hall of Freezers. Unlimited ice cream and #TeamMOIC guides are included. Plan for a playful, photo-friendly visit rather than a traditional museum with a detailed, room-by-room story.

“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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3.Back Bay Chocolate and Art Galleries Tour

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

Join guide Adam for a small-group, 2.5-hour walk through Boston’s Back Bay. Taste hot chocolate, a cookie, cupcake, and chocolate hazelnut cake, visit two art galleries, and hear about the neighborhood’s history and architecture. The route covers about 1.3 miles, starts by the Prudential Center, and ends on Clarendon Street.

“This was a great way to see Back Bay and lean some Boston history. The chocolate tastings were delicious. Adam is a very attentive guide. Highly recommend.”

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

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

Set sail from Boston’s Marina Overlook for a two-hour harbor cruise aboard a traditional tall ship. Your ticket includes coffee and pastries from Flour Bakery + Cafe, with $5 mimosas and other drinks available. The ship stays in motion and returns to the same pier. The crew includes Captain Fredo, Jess, and Max.

“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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5.Harvard Square Chocolate Tour

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

Meet your guide at 1400 Massachusetts Ave for a 90-minute chocolate walk through Harvard Square. Expect tastings of chocolate and other sweets, local independent shops, and stories connecting chocolate with Cambridge history. Guide Roberta has led the tour, though your guide may differ. Groups are capped at 12.

“Roberta was GREAT! Very informative and personable. Great energy the whole time. I would recommend her and the tour to anyone.”

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6.Back Bay Chocolate and Art Galleries Guided Tour

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

Spend 150 minutes walking Back Bay with a live English-speaking guide, tasting hot chocolate, cookies, cupcakes, and chocolate hazelnut cake bites at four stops, and visiting two art galleries. The tour meets at the Tesla showroom in the Prudential Center. Adam is the guide associated with the experience.

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

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7.Back Bay Evening Chocolate Tour

★★★★★★★★★★5.0 · 4 reviews · from $60

Spend two hours in Back Bay, tasting hot chocolate, a cookie, a cupcake, and chocolate hazelnut cake while visiting two art galleries and walking Newbury Street and Commonwealth Avenue Mall. The 7 pm tour starts by the Prudential Center and ends on Clarendon Street. Adam is named as a personable, adaptable host.

“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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