How To Do Boston in Two and a Half Days

I’ve wanted to visit Boston for about 20 years.  I’m a total history nerd.  There are some eras that I enjoy more than others, but when it comes to American history, I’m a sucker for it.  I get this from my dad and my Grandma Jane.

For as long as I can remember, they have loved history as much as I have.  My grandma taught 4th grade for years and the teachers always did a unit on Illinois history.  She and my grandpa took my cousins and me to Springfield to tour the Capitol and Abraham Lincoln’s house.  We are lucky enough to have the Fort Massac Encampment Reenactment, a reenactment of the Lincoln-Douglas Debates, the first bank in Illinois, all in our back yard.  I have so many fun memories of taking off on historical journeys with them.  My dad is a history teacher so, yeah, that’s pretty much all I need to say there.  The nut doesn’t fall far from the tree with this trait.

Now either my husband was sick of hearing me say I wanted to go to Boston or he is going for “Husband of the Year”.  I’m ok with whatever his reasoning was when he bought us tickets to Boston for our anniversary this year.  To say I was shocked was an understatement.

As soon as I could, I started researching and planning our trip.  I knew a few things I wanted to do, but I also wanted to make the trip for Neil too.  He doesn’t dig history quite as much as I do.  😉

After planning it out and experiencing it, here’s what I recommend for the top 5 sites to see while you’re in Boston.

We got the Boston Go Card which includes the entry fee to most of these places and many more that we didn’t get to make.

Freedom Trail

From the beginning to the end, you can get a guided tour of ALL the main historical sites from colonial Boston.  We did the first half guided, walking tour and we did the second half on our own.  Starting at Boston Common and ending in Charlestown, you get to see and learn so much by following the trail.

Fenway Park

TAKE THE TOUR!  It’s so worth it.  Even if you’re not a baseball fan, it’s truly a historical landmark.  You get to see and learn the coolest facts about the ballpark.


The first thing we did when we got settled in was head to the original Cheers on Beacon Hill.  There is a replica location at Faneuil Hall Marketplace.  I really wanted to see the place where the idea started.  Our hotel was about a block away from Boston Common.   I grew up watching this show with my parents and thanks to Netflix, I can watch every episode again.  You enjoy it in a totally different way as an adult.

TD Garden

We took a tour of the venue where the Boston Celtics and the Boston Bruins play.  Although the original Boston Garden was torn down when the new Garden was built and we didn’t get to step foot on the floor where the one and only Larry Legend played, it was still super cool to be where so many famous people have played.

Charlestown Navy Yard

WOW!  The Charlestown Navy Yard was something I didn’t really care if we went to at all when I was planning our trip and it was one of the biggest surprises for me.  The U.S.S. Constitution, the oldest commissioned battleship in the country is located at this navy yard.  You can walk around the deck and go under to see the quarters as well.  Another battleship, the U.S.S. Cassin Young was even cooler I thought.  About 70ish years old, this was way more modern and familiar looking.  I loved it and so did Neil.  The Charlestown Navy Yard is totally cool and a must see.

There were a few other places we wanted to visit, but there just wasn’t enough time in our long weekend.  I really wanted to go to Harvard and take the “Hah-vahd” tour as well as the Aquarium and the watching tour.  We also didn’t get to Mike’s Pastry, inside the Old North Church, the JFK Presidential Library and Museum.  I am dying to go to Martha’s Vineyard, Nantucket, and other places on the cape.  All in all this was an awesome trip and we will most definitely go back if we have the opportunity.  I hope the take the girls when they are a little older so they can enjoy this little piece of history just like I did.

Have you been to Boston?  What are you “must see” places?

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