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What are the top things to do in Boston if you only have a couple days? This was the question for the Jones Family when we had just two days in downtown Boston. It was time for another EPIC Jones Family road trip and we needed to visit 5 states in New England to get us closer to all 50. Boston was our first official stop and Massachusetts was the first of the five states.
Top Things to do in Boston
So, what did we decide we couldn’t miss in Boston? Keep reading for our list of the top things to do in Boston.
- Freedom Trail
- Fenway Park/Boston Red Sox
- Lobster Rolls
- Boston Tea Party Ship Tour
Boston Freedom Trail
The Freedom Trail is a unique collection of museums, churches, meeting houses, burying grounds, parks, a ship, and historic markers that tell the story of the American Revolution and beyond. You follow a red brick trail throughout downtown Boston to unique points of interest, each with a story of it’s own.

Rather than a guided tour, we chose to use the Freedom Trail app to guide and inform us as we strolled along the Trail. The app costs $9.99 for the full tour and we felt it was worth the price. Using your phone’s GPS, it will guide you along the trail and as you approach a point of interest, you will get an audio tour of that location as well as additional information about the historical figures and events involved in each spot.

The Trail extends for 2.5 miles, if you walk just the Trail. We found ourselves wandering through various locations along the Trail, so expect to walk much further than 2.5 miles. We did not finish the full trail and had over 4 miles on the day.

Right near the halfway point, Boston offers lots of opportunities to grab some food, including Little Italy. We stopped at Ernestos Pizza to grab the largest slices of pizza we’ve ever seen. For $6, you get a HUGE slice of pizza. This was the cheapest and best meal we had in Boston.

You can get on or off the Trail anywhere you’d like. We chose to start at the beginning in Boston Common and proceeded in order to Paul Revere’s church. For the American history buff, the locations are fantastic. Our kids experienced homeschool lessons in the actual locations where the history occurred. A truly “historic” occasion.
Lobster Rolls
Like most big cities, Boston offers the foodie many opportunities to sample the local fare. Everyone told us we HAD to get a lobster roll while we were in Bean Town. Of course, we can’t resist a good food recommendation, so we made sure this was our first meal in Boston.

We did a quick Yelp search and found many promising options for lobster rolls. We ended up deciding on Luke’s Lobster. They offer classic lobster rolls (meat cold, bun hot) and lots of local soda options.
I got the roll sampler, so I could try all three options; shrimp, crab, and lobster. The kids tried the clam chowder and Mommy got the standard lobster roll.
I actually liked the crab roll the best, followed by the shrimp, and lastly the lobster. They were all good, but the shrimp and crab just offered a lot more flavor than the lobster.

While Luke’s was conveniently located near our hotel and had great service, their prices are very high. It’s a fast food style “restaurant” where you order at the counter and sit down to eat or take it to go. For our family of four, we spent over $100 and the two kids didn’t even get a roll. Very spendy. Glad we got our lobster roll in Boston, but we’d probably choose a different option next time.
Fenway Park
Fenway Park is the oldest operating baseball stadium in the Major League. Though generations have come and gone, Fenway Park remains, much like it did the day it opened on April 20, 1912. The history and aura of Fenway are unmatched.

We considered going to a game at Fenway and when we saw they were playing the Tampa Bay Rays (from our home state of Florida), we knew we had to go. It was an awesome experience. We got ball park hot dogs and Cracker Jacks to complete the whole experience.

Boston Tea Party Ship Tours
We chose not to do the Boston Tea Party Ship and Museum Tours, as we just did not have enough time for everything. However, the Boston Tea Party occurred right behind our hotel!

At the Boston Tea Party Ships & Museum, you can be a part of the famous event that forever changed the course of American history through a multi-sensory experience that includes live actors, interactive exhibits, and full-scale replica 18th-century sailing vessels!
You can reenact the event that started a revolution! Experience life at sea aboard an 18th-century sailing vessel as you join a Son of Liberty and take part in the “Destruction of the Tea”! Throw tea into the very same body of water where the Boston Tea Party took place over 240 years ago.
Boston Must Do
As you can see, Boston offers the history buff a multitude of amazing experiences. So much American history occurred in this port city. Not to mention, so much baseball history!
Even with just a couple days, you can experience much of what Boston has to offer. What did we miss that you have on your list? Let us know in the comments.