Boston: Historic Taverns Tour, Harbor Ferry & Tastings

Summary

Boston’s oldest pubs, freedom trail stories & harbor breeze

You’ll walk Boston’s oldest streets with a local guide, raise a glass in two historic taverns once frequented by legends, cross Boston Harbor by ferry, and finish with real North End cannoli. Expect laughter, stories you’ll remember, and moments when history feels unexpectedly personal.

What’s the experience like?

The first thing I noticed was how the wooden floor creaked under my sneakers—like it remembered every footstep since Paul Revere. Our guide, Tom (Boston accent and all), grinned as he handed out the first round at the tavern. “This is where George Washington might’ve nursed a pint,” he said, and honestly, I could almost picture him in the corner, plotting something big. The beer tasted colder after that. Maybe it was just me getting swept up in it—or maybe it was actually cold in there; Boston’s weather does what it wants.

We’d started in the North End (Little Italy), dodging bakery smells and old men arguing about cannoli. After a quick walk to Long Wharf, the ferry across Boston Harbor felt like a breather—windy enough to mess up your hair, but you get that wide-open view of the skyline and suddenly history feels less like homework. Charlestown Navy Yard was next: I didn’t expect to care about ships but hearing about “Old Ironsides” from someone who clearly loved telling these stories made it stick. Bunker Hill loomed up gray against the sky—Tom told us about Dr. Warren and “don’t fire till you see the whites of their eyes.” Gave me chills for a second.

Back on land, we wandered past the Old State House (cobblestones everywhere—bring good shoes). There’s this spot where you stand right where the Boston Massacre happened; people mostly just walk by but Tom made us pause. It got quiet for a moment, which is rare in downtown Boston. Then we ducked into another tavern—the Green Dragon or maybe Bell in Hand (my memory’s fuzzy after two drinks)—and split some appetizers while Tom tried to teach us an old toast. I butchered it but nobody cared.

The last stop was back in the North End for cannoli—real ones, powdered sugar everywhere. I still think about that view from the ferry and how weirdly close you can feel to people who lived centuries ago just by sharing their haunts for an afternoon.

Step-by-step itinerary

Day 1 — Historic Boston Taverns and Harbor Tour

• Start tour in Boston's North End
• Walk to Long Wharf for ferry ride
• Ferry ride across Boston Harbor
• Visit Charlestown Navy Yard and USS Constitution
• Pass by Bunker Hill Monument
• Enjoy drink and appetizer at historic tavern
• Visit Old State House and Boston Massacre site
• Explore Faneuil Hall and Quincy Market
• Stop at Green Dragon or Bell in Hand Tavern
• Return to North End for cannoli treat

Top questions

How long is the Boston Historic Taverns Tour?

The tour lasts approximately 3.5 hours and covers about 2.5 miles on foot.

Are drinks included on this Boston taverns tour?

Yes, one drink (beer, wine or soda) is included at each of the two historic tavern stops.

Does this tour include food?

You’ll enjoy appetizers at both tavern stops plus a cannoli from a famous North End bakery at the end.

Is there a ferry ride during this tour?

Yes, there’s a public ferry ride across Boston Harbor between Long Wharf and Charlestown Navy Yard.

What historical sites are visited on this tour?

You’ll see five Freedom Trail sites including Bunker Hill Monument, Old State House, Faneuil Hall Marketplace and more.

Is this walking tour suitable for all fitness levels?

You should have at least moderate fitness; there’s about 2.5 miles of walking involved.

Does the tour operate in bad weather?

Yes, it runs rain or shine—or even snow! Dress appropriately for Boston weather.

Are children allowed on this tour?

The tour welcomes all ages; infants must sit on an adult’s lap if present.

What’s included

Your day includes two drinks (beer, wine or soda) with appetizers at historic taverns where legends once gathered, entry to five Freedom Trail sites with stories from your local guide, a scenic public ferry ride across Boston Harbor between neighborhoods, plus an authentic cannoli from a well-known North End bakery before wrapping up back where you started.