Liberosis Travels: Boston, MA

Our Boston Travel Itinerary

If you read my last Boston post, (catch up here if not) you know that I’m set on living there one day. But before I visited last week, I had never been there! Luckily, I loved the city as much, and more, than I thought I would. Here’s a breakdown of what we did each day.


  • Flew in (after 1 cancellation and 2 delays-phew!)
  • Walked from our hotel (Chandler Inn in Back Bay. I recommend it because it was the most reasonable hotel around and we were able to walk everywhere. Plus we had an awesome view from our room).
  • Ended up in the Public Gardens. This was easily my most favorite place in Boston! Look for their resident swans, Romeo and Juliet, if you go.
  • Stopped in the Boston Public Library. This place is unreal. You need to see it with your own eyes. They even have a beautiful courtyard!
  • Dinner at The Grotto in Beacon Hill. This place was recommended by both the travel books and other bloggers. It’s small and dark, so I would suggest making a reservation while there is still a little light out. We both had the lobster pasta and it was so yummy.


  • We got doughnuts and coffee at Blackbird Doughnuts and walked to the public gardens with it. It was so peaceful! We had perfect weather this day!
  • We rode the swan boats. The line was long with little kids, but the ride is only $3.50 and so worth it. This is one of the most signature experiences Boston has to offer.
  • Visited Beacon Hill. I seriously wish I could live there. I ended up finding where Louisa May Alcott grew up as well!
  • Visited the Boston Common, State House, and found the start of the Freedom Trail. The Trail is super touristy, but you have to do it. It makes it easy to navigate (follow the red brick line) your way all the way through the city while visiting all the major historical points. Most stops are either free or “pay what you wish” entry. I won’t recount everything we saw, but a couple of our favorites were the Paul Revere House, Quincy Market, and the USS Constitution. If you walk this, please wear tennis shoes. I wore flip flops and ripped my feet up. We stopped for lunch in Quincy market, where I had my first lobster roll. I’m pretty sure I could eat one every day!
  • Stopped at Mike’s Pastries. This is a famous pastry place in the Italian North End. We ended up walking the freedom trail all the way back as well, and stopped here on route. Don’t miss out on a canoli here!
  • Dinner at The Oyster Union House. It was cool to experience once, but I honestly won’t go back again. I went because it’s the oldest restaurant in America, but it felt super touristy despite the legitimate old feel of the building. Dinner was good, but expensive.
  • Got a cocktail at the top of the Prudential building. There’s a really expensive restaurant up there,but you can still go to the top for the view and a drink!


  • Took the T to Harvard. Taking the subway in Boston was actually super fast and easy! We walked around the Harvard Yard, bought some items at the bookstore, and got a drink at John Harvard’s pub.
  • The Boston Tea Party Museum. Admission is pricey ($28) and the place is touristy, but I actually loved this one. The guides do a great job of playing their parts, and each visitor is assigned a person from the tea party to be. It’s very interactive and the inside displays are very futuristic in nature (despite what they are about).
  • Harpoon Brewery. We were told to skip Sam Adams for this place, and I’m glad we did. I personally loved their Huckleberry beer. This place reminded me of MadTree here in Cincinnati. Tours cost $5. We didn’t book ahead, which is something I suggest you do, but we got a tour time anyways. It started pouring so we just sampled all the beers until our tour time. During the tour you get 30 minutes to sample all of the brews they have, which was pretty cool.
  • Dinner at Legal Harborside. This place is a chain, so you will see it all over Boston. I was told to still go, however, because it’s very good. We originally wanted a seat outside, but since it rained we missed out on our harbor view. We each ordered a whole lobster, which was quite the experience.

On our last morning, we took one last walk to the Public Gardens since it was our favorite place. There is so much more I could tell you about Boston, but it would take a few more blog posts or this will turn into a book! I loved the atmosphere, and people were a lot more friendly than we thought they would be. Plus, the city couldn’t be more beautiful! I can’t wait for a return trip.

PS. I also got engaged on this trip! I’ll post more on that soon!

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