Cocktails & Cannoli: Boston North End Dessert Tour

Dessert comes first on this tour, and the cannoli rivalry is settled by taste.

Cocktails & Cannoli is a 2-hour walking food tour through Boston's North End where you taste four desserts and three cocktails, skip the lines at two famous pastry shops, and learn the history of Paul Revere's House and Old North Church from a local guide. The tour includes a blind cannoli taste-off between two historic bakeries, a water bottle, and all samples. Minimum age is 21. Groups stay under 12 people on public tours, and dietary needs can be accommodated with advance notice.

Step-by-step itinerary

Dessert and historic walking tour

• Join all-inclusive dessert tour
• Receive water bottle
• Taste 4 dessert samples
• Taste 3 cocktail samples
• Visit Paul Revere’s House
• Discuss alcohol in Revolutionary Boston
• Skip lines at pastry shops
• Participate in blind cannoli taste off
• See Old North Church and signal lanterns

The experience

The tour starts with dessert instead of saving it for the end. You'll walk roughly 1.5 miles through the North End over about two hours, stopping at two of Boston's most famous pastry shops where the guide helps you skip the line. The cannoli here are the draw (thick shells, sweet ricotta filling), and you'll taste them at both places to settle which one wins. Gelato rounds out the dessert samples, and a local guide weaves in the neighborhood's history as you move between stops.

Three cocktail tastings happen alongside the sweets. The guide connects the drinks to Revolutionary Boston, explaining why alcohol mattered in the 1770s as you pass Paul Revere's House. You'll also see Old North Church and learn about the signal lanterns hung there in 1775: the "one if by land, two if by sea" moment. The guide brings cultural facts and culinary details that ground the neighborhood in something more than just the food.

Everything is included: the samples, the water bottle, the skip-the-line access, and the guide. You bring an appetite and a willingness to walk in whatever weather shows up. Gluten-free options are available if you mention dietary needs at booking, though not every location is completely allergen-free and some tastings are fixed offerings. The cannoli are not made in nut-free facilities.

What’s included

• Local guide leading the walk.
• four dessert samples including cannoli and gelato.
• three cocktail tastings.
• bottled water.
• skip-the-line access at two famous North End pastry shops.
• a blind cannoli taste-off between the two bakeries.
• stops at Paul Revere's House and Old North Church.

Before you book

Days and timesSaturday and SundayDeparts at 13:00

Book up to2h before

AgesAdult (21 and older) · Under 21: can't be included in the booking

GroupUp to 2

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.

Prices and times updated 4 days ago

Good to know

Easy physical levelPublic transport nearby

Operated by Cocktails & Cannoli

Is this one for you?The tour walks 1.5 miles at a steady pace over two hours, so choose it if you're comfortable on your feet and want to taste your way through the neighborhood rather than sit at a table. The dessert-first approach and the cannoli rivalry make sense only if you're willing to eat sweets before dinner.

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Top questions

What exactly do I taste on the Cocktails & Cannoli tour?

Four dessert samples including the classic cannoli and gelato, plus three cocktail tastings. The cannoli taste-off lets you compare the two bakeries' versions side by side.

Do I really skip the line at the pastry shops on this tour?

Yes. The tour includes skip-the-line access at two of the most famous pastry shops in the North End, so you avoid the wait that builds up during peak hours.

How far do we walk on this tour?

The tour covers approximately 1.5 miles over 2 to 2.5 hours, moving between the North End's dessert stops and historic sites. The pace is walking-based but suitable for all fitness levels.

What is the Paul Revere House stop about?

Paul Revere's House is one of the oldest buildings in Boston, and the guide discusses its role in Revolutionary history and the importance of alcohol during that era as you pass by.

Can I do this tour if I have dietary restrictions?

Gluten-free options are available if you mention your needs at booking. Let the operator know any dietary requirements in advance, though some tastings are fixed offerings and not every location is completely allergen-free.

What is the minimum age for this tour?

You must be at least 21 years old to join, since the tour includes three cocktail samples.