Boston Food & History: Pizza, North End & Freedom Trail

Your North End to the Freedom Trail combines our North End Food Tour and our History and Highlights Tour to make up a brilliant half day tour that will give you a comprehensive introduction to our fair city.
Your experience begins at the lifeblood of Boston, the Boston Harbor. Walk through a scenic waterfront park, with views of the harbor, East Boston and the historic wharfs lining Atlantic Ave. We’ll make our way to the heart of the North End, with views of some of the most historic sites and properties in the neighborhood, some dating back to the late 1600s and early 1700s.

We will pass by the Rose Fitzgerald Kennedy Greenway, a linear park located in several Downtown Boston neighborhoods. It consists of landscaped gardens, promenades, plazas, fountains, art, and specialty lighting systems.

Immerse yourself in the heart of Boston’s North End, where history and flavor come together. Start at a hidden Italian bakery, famous for its fresh, crusty bread made daily—a true neighborhood staple. Then, step into a traditional Italian salumeria and indulge in a classic deli sandwich layered with premium cured meats and cheeses, just like locals enjoy. Finally, take a mid-tour break at a bustling Hanover Street café, sipping an authentic Italian coffee while soaking up the lively atmosphere of this iconic corridor. This stop is a delicious journey through the North End’s culinary heritage.

You’ll hear stories about some of the most influential events that happened in Boston, including Paul Revere’s Midnight Ride. We will make our way to the Old North Church and step inside the hallowed walls.
The Old North Church is closed until the beginning of April. During this time, we will not be able to visit inside the church, but we will stop outside of it.

A short trek through Downtown Crossing

From Faneuil Hall, you’ll be able to see Custom House Tower, the first skyscraper built in the city of Boston and originally the location where incoming goods were stored upon arrival to Boston.

Moving into the heart of Downtown Boston, we stop in front of the Old State House. This is where the Declaration of Independence was announced to elated crowds in July 1776 - your guide will paint quite the picture for you of that exciting time in Boston. On the flip side, you’ll also hear about the tragic Boston Massacre that occurred here and what led up to that fateful day.

You can’t come to Boston and not mention the Boston Tea Party. While at this stop, which was originally a church, your guide will fill you in on all that led up to the infamous event. Learn who said “No taxation without representation!” and how Bostonians planned their act of rebellion in 1773.

Next we’ll pass by the site of the first bookstore in Boston, which has housed the publishers of Thoreau’s Walden, Hawthorne’s The Scarlet Letter, and Longfellow - you may have heard of his famous tale: Midnight Ride of Paul Revere.

This hall was home to the city council in the 19th and 20th century, as well as the site of the first public school in America. You’ll also marvel at its breathtaking French architecture and be able to snap a photo with the famed Bronze Donkey.

A short trek through Downtown Crossing and past the Old City Hall takes you to one of the most historic places in the country – King’s Chapel, the first Anglican church in New England. Your guide will teach you about its history and its progression through the centuries. If we're lucky, we could hear the organist practicing on the oldest church organ in the US.

Originally part of Boston Common, this cemetery dates back to 1660. Along the way, you’ll pass by the final resting spot of famous Revolutionary heroes like John Hancock, Paul Revere, and Sam Adams.

The oldest city park in the United States, Boston Common (not Commons) is a favorite with locals and visitors alike. Walking through the park, you’ll see various memorials, fountains, and recreation areas - which have been enjoyed daily since 1634.

One of the most popular and well-known neighborhoods in all of Boston, this area wasn’t always as attractive as it is today. You’ll peek down the cobbled streets as your guide shares the fascinating history of this area - how sailors and British soldiers in the 17th and 18th centuries actually decreased its favor for local residents and how it became the iconic and aspirational neighborhood it is today.

A lesser-known memorial, but one of great interest and significance. This memorial commemorates one of the first African American regiments in the Civil War and their colonel Robert Gould Shaw.

You’ll love seeing the glittering dome of the inspiring, historic, and beautiful Massachusetts State House. You may have heard of the original landowner for this site, John Hancock, and the man who presided over the cornerstone ceremony for the building in 1795, Paul Revere. Your guide will be sure to fill you in on how this building has lasted over the years and continues to be an integral part of the state’s government.

This garden is full of life with residents of modern Boston enjoying it for walks, exercise, fun, or just a peaceful moment. But as you walk through this picturesque park (the first public park in America), you’ll really be able to get a sense of how the land was used by Bostonians (and even British soldiers) throughout the revolution-era and since then as well. Your tour will end here - in the perfect central location for you to continue your day in Boston.