Boston History and Freedom Trail Private Walking Tour

  • 2-8 Hours
  • Walking Tour
  • Group price up to 12Groups of 13+ call to book
  • Private Tour
  • Daily

Highlights Tour

Boston is a magnet for history buffs as well as architecture lovers. Walk the parts of the iconic Freedom Trail and venture past the must-see historic stops in Boston. Visit Faneuil Hall and see where the first cries for Revolution rang out. Learn about some of the “events” that led to the American Revolution – like a tea party and a Boston massacre. See where the very first public school in America was located and how it connects us to modern public education. This 2-3–hour Boston tour will give you an overall history while also showing you how a modern city is intimately connected to the past.

Half-Day Tour

A half-day tour (4-5 hours) allows more opportunity to experience the top things to do in Boston.  Along with the must-see stops of the Highlights tour, you will also visit other famous neighborhoods and landmarks throughout the city. 

The North End is steeped in colonial history. We can tour where Paul Revere lived as well as the famous Old North Church, which played a very important role in the start of the American Revolution. This area is also well known for its Italian eateries, and there’s nothing like a delicious cappuccino and freshly made cannoli! 

You’ll also get to explore the narrow streets and beautiful architecture of Beacon Hill. This has always been the most sought-after and expensive neighborhood in Boston. You can play the real estate game while standing on the most expensive street of real estate in the city, and you’ll also see the most photographed street in Boston.

Full-Day Tour

Wear your comfortable walking shoes because this full-day Boston tour up to 8 hours can cover all of the stops along the Freedom Trail, from the State House atop Beacon Hill to the USS Constitution in the Charlestown Navy Yard. Your guide will give you the fascinating histories of all the must-see stops while also taking you to the much more hidden locations located just off the beaten path. We want you to feel like you’re spending the day with a friend who is showing you the most iconic locations and sharing the most incredible stories as you walk together through Boston and through history!

Walk down the tiny, picturesque colonial streets of Charlestown to the battlefield of Bunker Hill and learn about the brave stand that the colonists made against British tyranny right at the location where it happened.

We can also spend time taking in the North End, one of the most important neighborhoods in the city known not only for the incredible food scene but also its unforgettable mix of colonial history and modern true crime history.

We can also explore the story of the Boston Tea Party at the exact spot where it happened. Your expert tour guide can also take you to Boston’s newest neighborhood – the Seaport – filled with scenic harbor views and a tremendous collection of stores, cafes, and restaurants as well as secret spots to get incredible panoramic vistas of the entire city!

With the full-day Boston tour, your guide can also walk you through one of the most fascinating historical graveyards in America where so many founding fathers are buried. Hear unforgettable stories of Samuel Adams, John Hancock, and Paul Revere right where they are buried while also learning all the hidden secrets of Boston’s historic burying ground.

There’s also a chance to explore the culture and Victorian beauty of the Back Bay and stroll along the banks of the Charles River and the Esplanade while taking in amazing views of Boston and Cambridge. End the day out on tour with us with a cocktail at one of the many outdoor cafes on Newbury Street or a sweet delight from a famous local bakery! 

Community Impact

We mindfully design our tours to explore areas on foot, thus doing our part to lessen our environmental impact.

We are committed to a “360-degree view” of storytelling, featuring stories about under-represented groups, such as women, immigrants, and people of various ethnicities, ages, religions, and sexual orientations.

Our guides prioritize “supporting local” through recommending and patronizing family-run and locally owned businesses so that culture and traditions are preserved and are passed onto the next generation.

Our small-group tours minimize negative impacts on the local community, reducing pressure on small businesses we frequent, allowing locals more room to maneuver around our tours, and reducing noise pollution without the need of microphones


Back Bay

Built on reclaimed land originally part of the Charles River basin, this neighborhood is known for its luxury shopping, historic landmarks like Boston Public Library, and some of the city’s best preserved Victorian architecture.

Copley Square

This public square in Boston’s Back Bay neighborhood is ringed by several notable landmarks, including Boston Public Library, Trinity Church, and the tallest building in Boston, the John Hancock Tower.

Boston Public Garden

Located in the heart of Boston, this green space is known as America’s first public garden and is home to many monuments and memorials honoring the city’s most notable past residents.

Charles River Esplanade

Following the Charles River along the banks of the Back Bay neighborhood, this esplanade attracts all sorts of recreation and leisure activities, including performances at Hatch Memorial Shell.

Boston Common

This public park, one of the nation’s firsts, once served as a cemetery for many notable Bostonians as well as a campsite used by the British before the American Revolutionary War.

Beacon Hill

Your Boston walking tour passes through one of the prettiest neighborhoods of Boston, Beacon Hill. Upon this hill resides Massachusetts State House and where streets are lined with brick houses, cobblestone streets, small shops, and significant historic landmarks.

North End

The neighborhood of Boston’s North End is not only known for its historic buildings – including Paul Revere’s home and Old North Church – but also its excellent Italian eateries and local cafes carrying locally roasted Beantown coffee.

Old North Church

Built in 1723 and the oldest standing church building in Boston, Old North Church, a stop on your Freedom Trail tour segment, played an important role in the city’s colonial days leading up to the American Revolution.

Faneuil Hall Marketplace

Originally built as a public market house and assembly room, this landmark has more recently served as a site of significant speeches and houses unique shops, chain stores, food stands, and more.

Boston Public Library

This gorgeous landmark was established in 1852 as the first free library in America and its vast collection of millions of books, artifacts, and more make it the third-largest public library in the United States.

Freedom Trail

You’ll be discovering the history of the United States at several locations along this famous trail in Boston with a knowledgeable local guide to bring history to life!

Price Includes

Price Excludes

  • Local English-speaking guide
  • Food and drink
  • Museum/site admission
  • Souvenir and guide gratuity

Pickup Info

Start times: We offer pick up anytime between 9am-4pm

Pick up: This tour offers custom pick up and drop off (hotel,airports,etc)


Walking Tour

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