Private Walking Tour of Freedom Trail and Little Italy

See every site on the Freedom Trail! This walking tour includes all 16 stops on the Freedom Trail, covering historical sites such as the Paul Revere House, Copp’s Hill Burying Ground, Old North Church, USS Constitution, Boston Common, Old South Meeting House, Old State House, Bunker Hill Monument and more! Listen to hilarious stories from Boston’s past as you learn about the history of the area from a longtime resident, passionate historian, and former city employee. Tour includes a short walk through historic Little Italy.

Start the day in Boston Common, the oldest public park in the country. Listen to lesser-known stories told by the forgotten plaques and monuments of as you stroll this beautiful park.

Tour Boston’s most prestigious brownstone-lined neighborhood. Visit the “Most Photographed Street in North America”, featuring some of the original cobblestone. Stop by Louisburg Square, previously home to famous writers, today home to famous bankers and politicians.

Learn about the architecture and history of this famous building. Why is there a pine cone on top of the state house dome? What were the “King’s Pines” and why did the pine tree end up symbolizing the American revolution?

Visit one of America’s most historic cemeteries. Listen to stories of the American Revolution as you visit the graves of famous Founding Fathers Sam Adams, Paul Revere, John Hancock, and more

Visit Boston’s oldest cemetery, home to the graves of John Winthrop and William Dawes. Hear about King’s Chapel, Boston’s first Anglican Church, which was deeply despised by the local Puritans.

Visit the site of the Old Corner Bookstore, one of the most prolific publishing houses in early America. This building was where the first run of several important works was released, including Walden, The Scarlet Letter, Battle Hymn of the Republic, and Midnight Ride of Paul Revere.

View the building where the Boston Tea Party started. Listen to the story of one of Colonial America’s most famous rebellions. Hear how Sam Adams rallied the crowd to storm the ships in Boston Harbor and dump the tea in the water.

Learn about the “Cradle of Liberty,” where Sam Adams gave his famous speeches that united Boston against the British. Learn about the quirky history behind this building’s financial sponsor, Peter Faneuil.

See the oldest wooden building in downtown Boston, where Paul Revere lived for 20 years. Located on North Square, one of the oldest continually-inhabited areas of Boston, and former home to dignitaries such as Rose Fitzgerald Kennedy.

Learn about the immigrant past of Boston’s North End through public artwork installed on North Square

See the Old North Church and learn all about the midnight ride of Paul Revere and the historical inaccuracies of the famous poem!

Visit Boston’s second oldest burying ground, taking in view of the harbor and Charlestown, as well as the USS Constitution and Bunker Hill Monument. Learn all about Boston’s part in the events of the American Revolution.

Visit the historic outlook, where you can see Bunker Hill, the Charlestown Naval Yard, and the site of the Great Molasses Flood

• Infants and small children can ride in a pram or stroller
• Service animals allowed
• Public transportation options are available nearby
• Travelers should have at least a moderate level of physical fitness

• Private Walking Tour of Freedom Trail and Little Italy
  Add

• Tour guide is a long-time Boston resident & former City Hall employee

Trending Boston Nearby Tours Likely To Sell Out

Please be advised..

• This Tour is Provided by Boston Hidden Gems.
• Tour Timezone & Starts at America/New_York.
• Mobile or paper ticket accepted.
• For a full refund, cancel at least 24 hours before the scheduled departure time.
• Minimum 1 Travelers is required to book.
• Maximum 15 Travelers is accepted for booking.