Wondering if you can tackle Boston in just two days? Well, we have good news and bad news for you.
The bad news first: no, you can’t see the entire city in two days. It’s a city fraught with countless things to do and see that no one can see everything this bustling place has to offer in just two days.
And now for the good news: you can still see a whole lot of the city because Boston is quite a walkable city. In fact, it is the third most walkable city in the US and holds a walkability score of 82! It’s really no wonder that it’s been dubbed “The Walking City.”
Therefore, if you do only have two days to see Beantown, you will have to make some sacrifices, but you can still see plenty, especially if you follow our guide to having the perfect 2 days in Boston.
Experts Tip: There are plenty of free things to do in Boston, so you don’t have to break the bank during a weekend away.
What to Do in 2 Days in Boston: Day 1
Start with a Cup o’ Joe
Fun fact for you: Dunkin Donuts started in Quincy, which is just down the road from central Boston! This fact alone alludes to the locals’ love for the beloved coffee bean (this really adds a second reason for it being nicknamed “Beantown,” in our opinion).
Before you start your first day of exploring, be sure to do as the locals do and get a cup o’ joe. Head to either the nearby Dunkin or up your coffee game by trying your nearest Tatte Bakery & Cafe or Thinking Cup (165 Tremont Street), two of the best coffee shops in Boston.
Follow the Freedom Trail
The Freedom Trail is the best place to start your sightseeing adventure as it is the most efficient way of seeing the significant historical landmarks in the city. This 2.5-mile-long walking trail has its starting point at Boston Common and ends at Bunker Hill Monument. You can even eat your way through the Freedom Trail when you join our Best of Boston food tour!
The 16 authentic and historical stops along the trail include the following in sequential order:
- Boston Common – America’s oldest park, dating back to 1634
- Massachusetts State House
- Park Street Church – the first landmark of Boston
- Old Granary Burying Ground – the resting place for many famous patriots and heroes from the Revolutionary War
- King’s Chapel
- King’s Chapel Burying Ground – Boston’s oldest graveyard
- Boston Latin School Site and Benjamin Franklin Statue
- Old Corner Bookstore
- Old South Meeting House
- Old State House
- Boston Massacre Site
- Faneuil Hall Marketplace
- Paul Revere House
- Old North Church
- Copp’s Hill Burial Ground – second oldest graveyard in Boston and was used by the Redcoats for target practice
- USS Constitution – the oldest commissioned warship that is still afloat in the world
- Bunker Hill Monument – a monument commemorating the first major battle of the Revolutionary War
When you do intend on following the Freedom Trail, make sure that the indoor sites you’d like to see have visitor hours that correlate with your trail-blazing time. Allow yourself at the very least a couple of hours for the entire trail as well.
After you finish up the Freedom Trail, be sure to either explore Charlestown yourself or take a taxi (Uber and Lyft are your best options) or the subway (called “the T”) back into the downtown area.
Stroll Through the Boston Public Gardens
Right next to Boston Common lies Boston Public Gardens, which are the oldest botanical gardens in the United States. These beautiful gardens feature a quaint pond (which turns into an ice rink in the winter), swan boats, an enamoring bridge, and thousands of vibrant tulips in the spring.
One of the must-see features in the Public Gardens is the “Make Way for Ducklings” statues, which feature a wandering duck family. These statues are easy to love for both children and adults!
The Historical North End aka Boston’s “Little Italy”
Wind down your exploratory day with a short walk through the historical North End, which is also named Boston’s Little Italy. Stroll through the windy, snug cobblestone streets and top off your busy day with some of the best Italian dishes in the city.
Slurp up some heavenly spaghetti or other Italian favorites at nearly any place you find, but you should certainly highly consider doing so at The Daily Catch (sensational Sicilian-style food), Carmelina’s, Neptune Oyster, Bricco, and Table.
Don’t forget to treat yourself to something sweet from either Bova’s Bakery (134 Salem Street, Boston, MA 02113), Modern Pastry, or Mike’s Pastry!
What to Do in 2 Days in Boston: Day 2
Hit the Harbor
Boston Duck Tours, cruises, kayaks, Codzilla high-speed boat– any way you can and want to do it, we highly recommend you hit the harbor. Boston Harbor is a significant sightseeing point in the city and is a highly historical body of water.
Eat a Fresh Seafood Lunch
After cruising on the high seas (sort of), you’ll likely have a hankering for some fresh seafood–and Boston is an excellent place to indulge in such.
The Barking Crab (88 Sleeper St, Boston, MA 02210), Atlantic Fish Co., Neptune Oyster, Saltie Girl, B&G Oysters (550 Tremont St, Boston, MA 02116)…the stellar seafood venues are endless.
Boston Tea Party Ships & Museum
Now for one of the most quintessential Boston things to do: visiting the Boston Tea Party Ships & Museum. This entertaining and educational floating museum is one to not be missed as visitors can learn about the Boston Tea Party, which occurred on December 16, 1773, with the assistance of live actors and interactive exhibits!
Fenway Park
When in Boston, do as the Bostonians do– watch the Sox play at Fenway Park! And don’t worry: you won’t break the bank doing so. You can find pretty cheap seats available, especially when you consider the bleacher seats!
Afterward, be sure to go bar-hopping outside “America’s most beloved ballpark” for the full, local experience!
Is there no game on when you’re visiting? No problem because you can also enjoy a guided tour of Fenway “Pahk.”
Grab a Beer at the Green Dragon Tavern
The Green Dragon Tavern is one of the perfect spots to enjoy a frothy brew in Boston as it is where Paul Revere, Samuel Adams, and John Hancock frequented. This historical pub was a place in which the Freemasons and the Sons of Liberty met.
Today, the friendly staff continues to serve its patrons refreshing and delectable drinks that don’t break the bank! And we like to think the founding fathers would be proud of that.
Your 2 days in Boston will admittedly be pretty packed, but we know you’ll have a great time no matter what you end up doing! Remember to simply enjoy yourself and soak in the unique city that is Boston.
