Boston in 2 Days

Unlike the chaos of New York City, Boston is a clean and quaint city known for its academics and historical significance. Easily accessible via the Boston Logan International Airport, it is undeniably one of the best East Coast cities to add to your USA itinerary. 

If you are thinking of visiting Boston as a day trip from New York City, also check out the Planes and Plans New York City Travel Guide. 


Table of Contents

Boston Itinerary


Boston Common

Start your morning in the lush gardens of Boston Common. In fact, this public park is actually America’s oldest, and continues to be filled with cute dogs and groups of picnic goers. It is also the site of many political campaigns and social activism conducted by influential historical figures. Boston Common also marks the beginning of the Freedom Trail. 

The Freedom Trail

For those interested in American History, The Freedom Trail is one of the most unique ways to (literally) step back in time to the American Revolution. The Freedom Trail is a 2.5mi (4km) walk that weaves its way through downtown Boston. Along the way, you will pass key historical monuments that played a part not only in the city’s history, but also in shaping the current United States’ system of government. The trail starts at Boston Common, and ends at the USS Constitution Museum. Some of my favourite stops included the Old Corner Book Store and Faneuil Hall.

My recommendation is to join one of the official Freedom Trail tours for USD$17*. This way, you will be walked through the city by an expert guide as you hear stories of the American Revolution. 

Quincy Market

Quincy Market is located near Faneuil Hall, and is the perfect lunch stop along The Freedom Trail. The historic building houses street vendors and craftsmen, serving up deliciously hearty meals and fun souvenirs. It is also the best place to try some famous New England delicacies. Boston Chowda Co. is famous for its fresh clam chowder, whilst lobster rolls and Boston cream pie are additional must-try dishes. 

Boston Tea Party Ships & Museum

For a step back in time to the beginning of the American Revolution, pay a visit to Boston Tea Party Ships & Museum. The Boston Tea Party was undoubtedly one of the most significant events in American History, and the museum provides many interactive exhibits to aid your understanding of the event and its consequences. I particularly enjoyed being able to step directly onto the Tea Party Ships, as well as the incredibly informative tour guides working at the museum. 

Tickets can be purchased online for USD$34*. 

Boston, MA, USA


Harvard University

Boston is fortunately home to perhaps the most famous university in the world, Harvard University. Venture out to Cambridge this morning to explore its beautiful campus for yourself. Despite still being home to a large student body, the campus itself is filled with so much history, having being home to alumni such as President John F. Kennedy, President Barack Obama, Matt Damon, Natalie Portman, and many others. 

For those looking to learn more in-depth about the university’s history, I recommend embarking on one of the official Harvard tours. The Official Historical Tour of Harvard is a great free option, in which a student will take you on a one-hour walk through the lush campus grounds. There is also the option to take a self-guided tour through the Visit Harvard app. Make sure to rub John Harvard’s foot for good luck along the way! 


Located just across the Charles River from Harvard University, Massachusetts Institute of Technology (MIT) is another world-class university specialising in STEM. The campus is a mix of both historic buildings, such as the Great Dome, as well as modern artworks, especially those found at the List Visual Arts Center. 

Fenway Park

Whilst Boston has been made famous by its historical significance, the Red Sox’s baseball success has undoubtedly contributed to the city’s reputation. Fenway Park is home to the Boston Red Sox, and is often referred to as ‘America’s favourite ballpark’. Taking a tour of the beloved stadium is a must-do activity whilst in Boston. The one-hour tour will walk you around the stadium whilst sharing the team’s stories and history. It is certainly a fun way to learn about Boston’s buzzing sports scene! 

Tickets should be purchased ahead of time via the Fenway Park website, from USD$25*. Super fans also have the option to upgrade to a premium tour on game days.

*Please note that all prices are current as of the publication date of this post.

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