Boston Itinerary

Things to do in Boston

3-4 day Boston ItineraryBoston is one of the oldest cities in the United States. Riddled with its stake in the American Revolutionary War and the making of America, this is one of the main reasons for tourist to be attracted in general. For Peter and myself, we knew we wanted to visit after I was accepted into Grad School at Boston University. In just a few short days we got to explore many of the mainstream locations as well as neighborhood events that aren’t published for the world to see, just by walking through the city.

Here are some great things to look for and explore on your visit to Boston. 

Boston Aquarium

The first day of our trip it was pouring. We had not come fully prepared for anything but sun and we were not about to spend $10 on a piece of plastic to keep us dry. So we headed out, one raincoat in hand & off to the aquarium we went. When we arrived, the line for tickets was wrapped around the block, most likely because everyone else had the same idea of getting out of the rain. Instead of standing in a 2hour line, I hopped onto my phone, punched in my credit card number on the aquarium’s website and within 5 minutes we were inside enjoying the animals.

Something to keep in mind when it comes to visiting an indoor attraction on a rainy day… it will be crowded!!!

The aquarium changed some of the exhibits since the last time I was there as a kid, but overall it was enjoyable to see all the animals.

The Old North Church

On the quest to Bunker Hill, we saw a sign for Catacombs.


I wondered how they compared to those I have visited in other locations like Rome, Italy. So we decided to head towards the church for the tour. On our way, we were delighted to find an Italian Festival going on where we stopped and grabbed some lunch and sat in the local park listening to the music. It’s amazing what you can find when you don’t have a full set agenda!

The catacombs where interesting to learn about, housed under the church the history around it gives it some interesting appeal. It was still under excavation, which makes me wonder if they will find any more interesting things on their digs or if what they have learned so far is all they will ever know.

Bunker Hill

After the adventures with walking around Little Italy, aka the North End. Peter was determined to make our way to Bunker Hill. The history of Bunker Hill started in June 1775 when New England faced their battle with the British during the Revolutionary War. The monument that stands on the land of one of the bloodiest battles for Massachusetts is what tourist see today.

While you can climb the stairs to see the land, Peter and myself opted not too. We had walked over 8 miles that day and it was a unanimous decision in which we avoided boy scout troops and being outshined by a three-year-old who could climb better than myself on good days. We know what you are thinking… you are wrong!

*** Side note: I had knee surgery a few years ago & have not gained full mobility since. Some days are way better than others, stairs are not my friend any day! ***

So instead we opted to practice our modeling.

You can learn more about Bunker Hill’s History Here!

Old State House

Just outside of the Old State House is where the Boston Massacre occurred. The State House provides a look into life prior to the Revolutionary War and where “…Independence was born” (according to John Adams, for full quote and history please see the linked website).

You can take a tour or walk around on your own learning how America started its journey towards separation from England throughout the building. You will be able to learn about the Massacre, the lives of individuals of different statues and much more in this small but unique building and museum.

The best part of this location is you knock two things off your to-do list at once because once you leave you can stand outside in the memorial area where the Boston Massacre happened!

*Note: Just a few blocks from the Old State House is a market area that certain times of the week you can get amazing deals on fresh fruits and veggies.*

Faneuil Hall

The Faneuil Hall was a hot spot on Peter’s want list. What we didn’t know was that the hall took on a slightly different take from its historical purposes and housed a marketplace on the first floor. The hall itself, on the second floor, was grand, but the building lost it’s appeal when it was inundated with commercialism.

Outside of Faneuil Hall is a great little square where you can get a meal and some gifts it’s also where we met one of my idols Josh Gates. Ok, I owe Peter all the thanks for just walking up to him. I can be extremely shy and introverted in these situations, but Peter not at all.

Besides feeling extremely short, it felt good to meet someone I looked up too. I love the Travel Channel and the History channel. Heck, that’s probably why this blog has become a full development of everything I’ve worked so hard on. So I’m extremely thankful that Peter stepped up to talk to him.

Boston Commons

All I’m going to say about this is Cookie Monstah Food Truck!

Old Corner Book Store

I love books! You can follow our GoodReads on our page that’s how much I love to read. So when Peter mentioned this spot on the Freedom Trail I was all for it.

However, this was by far the biggest let down on the trip because we were greeted with a plaque on the front of a Chipotle giving us the details of the history. This is what I think most history lovers may collectively hate the most. Seeing a piece of our history changed and forgotten instead of revived to be cherished.

While I took a picture next to the plaque I’ll let the reality of it set in for all who want to adventure towards this piece of history on what is now lost. And once you have finished there is an ally just down the street that houses a great collection of books call Commonwealth Books that you should go check out!

Outside of Boston

If you are staying longer than 3 days in Boston or want to get out of the city check out these 16 Day trips from Boston from Travels with the Crew.

The Portly Passengers

The Portly Passengers provides plus size inclusive travel tips and advice for anyone who is looking to explore the world. From seat sizes on airplanes to exploring museums, restaurants, and nature Melissa & Peter have the experience and stories to help guide you through it.

Melissa & Peter are a couple of goofballs who are in love with traveling & each other.


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