Harvard University, Boston, USA
John Harvard Statue, Boston, USA

Two Days in Boston: Massachusetts Getaway

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 the city as a day trip from New York City, also check out the Planes and Plans New York City Travel Guide. 

Last updated January 2025*.

Is two days in Boston enough time?

Two days is the perfect amount of time for a fun weekend getaway to Boston. Since it is only a small city, many of the top attractions are located along within walking distance of downtown. However, the city also has a subway network connecting more distant neighbourhoods, including Cambridge.

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Table of Contents

Two Days in Boston - Itinerary

Boston Day 1 - The Freedom Trail & Boston Tea Party

Boston Common

Start your morning in the lush gardens of Boston Common. This public park is in fact America’s oldest, and continues to be filled with cute dogs and groups of picnic goers. The park is the site of many political campaigns and social activism movements, as well as marking the beginning of the Freedom Trail (see below).

Freedom Trail, Boston, USA
Faneuil Hall, Boston, USA

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 . The Freedom Trail is a 2.5mi (4km) walk, along which lies key historical monuments from the American Revolution. Many of these played a significant part not only in the city’s history, but also in shaping the current United States’ system of government. The trail conveniently 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.

The best way to experience the Freedom Trail is to join one of the 90-minute official Freedom Trail tours for USD$17*. 

Quincy Market

Located near Faneuil Hall, Quincy Market and is the perfect lunch stop at the end of 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 also must-try dishes. 

Boston Tea Party Museum, USA
Boston Tea Party Ship, USA

Boston Tea Party Ships & Museum

Pay a visit to Boston Tea Party Ships & Museum, the location where one of the most significant events in American History took place. The museum provides many interactive exhibits to aid your understanding of the event and its consequences. I particularly enjoyed being able to step onto the actual Tea Party Ships, as well as the informative tour guides working at the museum. 

Tickets can be purchased online for USD$35*. 

Boston Day 2 - Cambridge & Fenway Park

Harvard Gate, Boston, USA
Harvard Dorms, Boston, USA

Harvard University

Perhaps the most famous university in the world, Harvard University, is located across the river in Cambridge. Having being home to notable alumni including President John F. Kennedy, President Barack Obama, Matt Damon and Natalie Portman, the campus is filled with history and tradition.

I recommend embarking on one of the official Harvard tours to learn more about the institution. The Official Historical Tour of Harvard is a student-led, free option, which will guide you through the lush campus grounds. Taking a self-guided tour through the Visit Harvard app is another free option. However, you choose to explore, be sure to rub John Harvard’s foot for good luck along the way!

MIT

Located nearby Harvard University, Massachusetts Institute of Technology (MIT) is another world-class research and education institution 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 the city has been made famous by its historical significance, the Red Sox’s success has undoubtedly contributed to the city’s reputation. Fenway Park is home to the Boston Red Sox baseball team, and taking a tour of ‘America’s favourite ballpark” is a must-do activity whilst in the city. 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 January 2025.

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