Boston North End: Pizza Walking Tour & Freedom Trail Slices

Summary

Pizza, stories, and old streets in Boston’s North End

You’ll walk Boston’s North End with a local guide, taste three different pizza slices (each one seriously unique), hear stories at Freedom Trail sites like Paul Revere House and Old North Church, and finish with a fresh cannoli at Modern Pastry. Expect laughter, real neighborhood energy, and a few surprises along these old brick streets.

What’s the experience like?

The first thing I noticed was the smell — that sweet, yeasty cloud from Modern Pastry as we met outside. Our guide, Sam (he grew up three blocks away), waved us over and started telling us about the rivalry between Modern and Mike’s. I tried not to stare at the cannoli in the window. We set off down Hanover Street, dodging locals with shopping bags and hearing Italian mixed with Boston accents. The bricks underfoot felt uneven but solid — you could almost picture Paul Revere sprinting past us, honestly.

We stopped for our first slice at a place Sam claimed had the “best crust in Boston.” I burned my tongue a little because I couldn’t wait. The cheese was bubbling hot and there was this faint char on the bottom — not too thick, not floppy either. Someone asked about the Skinny House and Sam pointed it out: just wedged in between two buildings like an afterthought. He told us it was built out of spite (which made me laugh), and then we wandered past Old North Church where bells were ringing for a wedding. The whole street smelled like basil and garlic drifting from open kitchen doors.

I didn’t expect to feel so connected to the history here — hearing about Copp’s Hill Burying Ground while licking tomato sauce off my fingers felt oddly right. There was a moment by the USS Constitution where the wind picked up and you could hear gulls over the harbor; I caught myself thinking how many layers this city has. We finished back at Modern Pastry with a cannoli that actually cracked when I bit into it (I got powdered sugar everywhere). Still think about that view of Bunker Hill from across the river — kind of makes you want to come back just for another slice.

Step-by-step itinerary

Day 1 — Boston North End Pizza and History Tour

• Begin at Modern Pastry Shop
• Visit Paul Revere House
• See Old North Church
• Explore North End neighborhood
• View Boston's Skinny House
• Visit Copp's Hill Burying Ground
• See USS Constitution ship
• View Bunker Hill Monument
• Enjoy three pizza slices at top pizzerias
• Finish with cannoli at Modern Pastry

Top questions

How long is the Boston pizza walking tour?

The tour lasts about 2.5 hours through Boston’s North End.

Is food included on this Boston pizza tour?

Yes, three pizza tastings plus a cannoli from Modern Pastry are included.

Where does the tour start?

The tour begins downstairs at Modern Pastry Shop in Boston’s North End.

Are there gluten-free or vegan options available?

No, special diets are only accommodated on private tours—not public ones.

What historical sites are visited on this tour?

You’ll see five Freedom Trail sites including Paul Revere House, Old North Church, Copp’s Hill Burying Ground, USS Constitution, and Bunker Hill Monument.

Is bottled water provided during the tour?

Yes, bottled water is included for each guest.

Does this tour run in bad weather?

Yes, it operates rain or shine—dress appropriately for conditions.

Can children join this pizza walking tour?

Yes, children are welcome; infants can ride in prams or strollers.

What’s included

Your day includes three slices from top pizzerias in Boston’s North End (each one different), entry into stories behind five Freedom Trail landmarks with your local guide leading the way, bottled water throughout, plus a fresh cannoli from Modern Pastry to end things on a sweet note before heading out again into those lively city streets.