Boston Private 5-Hour Driving Tour

Your private driving tour starts in the heart of the city, where you’ll dive into early American history by visiting the top attractions in Boston along the famous 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!

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, food stands, and more.

Our tour will pass by this world-renowned baseball stadium, home of the Major League Baseball team Boston Red Sox since 1912!

You’ll love seeing the glittering dome of the inspiring, historic, and beautiful Massachusetts State House, designed and built by famous federalist architect Charles Bulfinch in 1798. From the outside, take in the views of modern Boston, including the skyscrapers of downtown, the Financial District, and the tallest building in New England: The John Hancock Tower.

You can’t come to Boston and not mention the Boston Tea Party. This location, in-fact a church, is where it all began - one night in 1773, when it was the largest building in the city! Stop here with your tour guide to learn more about this historic building.

As our tour explores the heart of downtown Boston, we’ll stop in front of the Old State House and site of the Boston Massacre. The Old State House is one of the oldest public buildings in the country. Your tour guide will educate you on its rich history and why it is so important today.

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

We’ll pass by this national historical landmark on our Boston history tour to learn more about the early days of the market and how it has transformed over the years.

This newer Boston neighborhood draws visitors for its city views and shopping. We’ll stop here on our tour to enjoy its harbor views, artwork, and restaurants – your tour guide will have recommendations on where to get some great New England seafood!

Enjoy views of Boston along this peaceful shoreline walkway around the Boston harbor.

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.

An excellent example of Richardsonian Romanesque style, this work of art and architecture was built between 1872 and 1877, and its intricate exterior and interior is sure to impress anyone!

We can stop at Boston’s most beloved sculpture, Make Way for Ducklings, based on the 1941 children's book written and illustrated by Robert McCloskey.

Your Boston 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.

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.

Built in 1723 and the oldest standing church building in Boston, Old North Church played an important role in the city’s colonial days leading up to the American Revolution. On certain days, we may be able to enter the church to learn more about its fascinating history!

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.

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.

Your Boston driving tour will include a stop at the plaza in the heart of Harvard Square, which serves as a meeting point for local residents and, in particular, Harvard students, who come here to enjoy the area’s many stores, coffee shops, and entertainment venues.

Your Boston sightseeing tour can include a walk through this Ivy League university that is the oldest institution of higher learning in the United States. The school is known for its beautiful campus, historic buildings, many styles of architecture, movie filming locations, and its long history of notable graduates.

Your Hahvahd Tour will pass by this stately bronze likeness of John Harvard, an English minister who supported the school in the early days of America’s colonial period. The sculpture is also interestingly nicknamed the “statue of three lies”...

This historic house once served as headquarters for General George Washington during the Siege of Boston at the opening phase of the American Revolutionary War. Arrange admission in advance with our team to take a tour of this handsome home!

This granite obelisk, erected between 1825 and 1843, marks the pivotal 1775 Battle of Bunker Hill, one of the first major battles between the Red Coats and Patriots in the American Revolutionary War.

Enjoy a walk down this charming cobblestoned street in the Beacon Hill neighborhood. Your tour guide will help you imagine what life might have been like in 19th century America on what is now considered the most photographed street in the U.S.!

The oldest commissioned ship in the Navy, U.S.S. Constitution, sits in the waters off the Charlestown neighborhood and can be toured for more information about its illustrious history.

While we’re exploring the northside neighborhood of Charlestown and its Navy Yard, we can include admission to this museum dedicated to telling the story of the USS Constitution and its vital role in the War of 1812.

This beautifully landscaped cemetery – the first garden cemetery in the United States – serves as both a resting place for many notable Boston elites as well as an arboretum for a variety of trees. Find out from your local tour guide what sets this National Historic Landmark apart from other cemeteries!