Boston: Pizza & Freedom Trail Walking Tour with Cannoli

Three Full Pizza Slices & Five Freedom Trail Sites in One Walk

You walk Boston's North End for 2.5 hours, eat three full pizza slices from different pizzerias, pass five Freedom Trail sites including Paul Revere House and Old North Church, see USS Constitution and Bunker Hill Monument, and finish with a free cannoli at Modern Pastry. Your guide is local, water is included, and the whole thing costs less than a sit-down dinner.

Step-by-step itinerary

Boston North End Pizza and History Tour

• Begin at Modern Pastry Shop
• Visit Paul Revere House
• See Old North Church
• Explore North End oldest section
• Hear story of Boston's Skinny House
• Visit Copp's Hill Burying Ground
• View USS Constitution ship
• Enjoy Bunker Hill Monument view
• Return to Modern Pastry for cannoli

The experience

So you're hungry and you want to actually eat, not just taste a sliver of something while someone talks at you: yeah, this Boston pizza tour gets that. You get three full-size slices from different North End pizzerias, the kind of places that have been doing this for decades. One of them's been running since 1883 with the original brick oven still going. Another won Boston's first pizza festival. The guide knows the neighborhood inside out and walks you past the Paul Revere House (oldest home downtown, built around 1680), Old North Church where the whole "one if by land, two if by sea" signal happened, and you'll see the Skinny House. This tiny spite house squeezed between two buildings that's exactly as weird as it sounds.

The walk covers about 2.5 hours through the North End, which is basically Boston's old Italian neighborhood packed into a few blocks. You'll pass Copp's Hill Burying Ground (second oldest cemetery in the city, and yeah, there's a Salem Witch Trials connection), then head over to see USS Constitution: the actual ship from 1797 that's still floating and still technically active. From there you get a view of Bunker Hill Monument, where the first major battle of the Revolution happened. It's not a museum tour where you're stuck inside. You're walking the actual streets, stopping for pizza, and the history just lives there in the buildings and the stories your guide tells. The whole thing starts and ends at Modern Pastry, which locals will tell you beats the other famous pastry place in the neighborhood, and you get a free cannoli at the end that's made in-house.

Water's included, the guide is someone who actually knows Boston (the reviews are solid), and you're not paying a fortune for this. The only real constraint is you need at least four people for a public tour to run, so if you're booking solo or with one other person, check the date or ask about private options. Gluten-free, dairy-free and vegan diets aren't available on the public tours. Those only work on private bookings.

What’s included

Your tour includes a 2.5-hour guided walk through Boston's North End with a local guide, three full-size pizza slices from different pizzerias, a free cannoli from Modern Pastry, bottled water, and stops at five Freedom Trail sites including the Paul Revere House, Old North Church, Copp's Hill Burying Ground, USS Constitution, and views of Bunker Hill Monument. You'll also see the Skinny House and hear stories about the neighborhood's history from Puritan times through its Italian heritage today.

Before you book

Days and timesEvery dayDepartures at 11:00, 14:00 and 17:00

Book up to1h before

GroupUp to 12

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.It may be canceled due to bad weather or if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated today

Good to know

Easy physical levelStroller friendlyPets welcomePublic transport nearby

Operated by Boston Pizza Tours

Is this one for you?Book this if you want to eat real food (not samples) while learning Boston history on foot, and you'd rather have a local guide handle the route and the stories than figure out the Freedom Trail yourself. The fixed 2.5-hour window and included pizza and cannoli mean you know exactly what you're getting and what it costs.

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Top questions

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

How many pizza slices do you actually get?

Three full-size slices from different pizzerias, not samples. They may include a slice ranked in the top 25 best in America, one from Boston's oldest pizzeria with an 1883 brick oven, or Neapolitan-style from a pizza festival winner.

How long is the tour?

2.5 hours of walking through the North End, with stops for pizza, history sites, and pastry.

What Freedom Trail sites do you see?

Five sites: Paul Revere House, Old North Church, the Skinny House, Copp's Hill Burying Ground, USS Constitution, and views of Bunker Hill Monument.

Is admission to attractions included?

No. You see the exteriors and learn the history from your guide, but admission fees to buildings are not included in the tour price.

What if I have dietary restrictions?

Gluten-free, dairy-free and vegan options are not available on public tours. Private tours can accommodate special diets.

What's included in the price?

The 2.5-hour guided walk, three pizza slices, a cannoli from Modern Pastry, bottled water, and a local guide.

What's the minimum group size?

Four travelers. If the minimum isn't met, the operator offers an alternative date or full refund.

Can I bring a stroller or wheelchair?

Strollers and prams are fine for infants and small children. The tour is suitable for all fitness levels, though it's a walking tour through city streets.

Does the tour run in bad weather?

Yes, it operates in all weather. Dress appropriately for the conditions.

Where does the tour start and end?

Both at Modern Pastry Shop in the North End, where you also get your free cannoli at the finish.