Boston Travel Must Do's // CEO in Progress

Summertime in Boston: My Travel Must-Do’s

I love writing about our adventures after the fact. Every time I do I get to relive all of the fun and remember my favorite spots and things we did. This latest adventure took us to Boston, and it was the first time traveling longer distance with our favorite couple to visit a friend from school. We spent the long weekend following the freedom trail, catching a game at Fenway, and drinking a Sam Adams or two. We had such a great time exploring and trying something new, we traveled really well together. We’re both planners, but like to go with the flow, and will also always break for cute shops & ice cream.

It was a great city to spend a weekend, there’s so much to see and always something going on. When we were there we hit up all of the major sites we possibly could, but also made time for some different things going on like ScooperBowl, aka unlimited ice cream tasting event. Heaven.

Summertime in Boston // CEO in Progress

I’m always amazed at how much we can pack in to a long weekend. We walked over 50 miles that weekend, but it let us see so much of this really amazing city. I honestly think it is my second favorite to Charleston; the history, the beautiful neighborhoods, the amount of cannolis, what’s not to love?! Everywhere we turned there was such a variety of events and attractions, plus there were a lot free tours that we were able to take advantage of. That was my one complaint about Nashville, a lot of the big things I wanted to do all had costly admissions.

We did cover a lot, and Amanda was a great tour guide, making sure we got to hit all the highlights and knew what time the Sam Adams tour started. Out of all of the things that we did, here’s a few of my favorites that you need to do when you visit. Hopefully I’ll get the chance to expand some more of what we did in the future, stay tuned for more photos and deets!

Boston Travel Must Do's // CEO in Progress


Walk The Freedom Trail

The Freedom Trail was a great way to spend an afternoon, I think it took us about 4 hours to complete (we breaked for lunch and margs of course) and it gave you such a really in-depth tour of the downtown. Plus it stopped at historical places that we might have missed if we just walked around on our own. The trail starts at Boston Common and you can easily follow the red brick path through the city all the way to the USS Constitution. If you go, I would recommend getting a guide on it (here’s a free one) so that you can learn about why these places are on the map. I would also suggest stopping at as many places that offer free tours/talks; Faneuil Hall was one of our favorites along the path.

Take a (Free!) Brew Tour at Sam Adams

Located in Jamaica Plain, the cutest little neighborhood, is the R&D center and original home of Samuel Adams. There they offer free tours of the brewing facility and explain the ingredients and steps of making their famous brews, plus there’s a taste test too! We spent about an hour or so there and got there pretty early so didn’t have to wait. This does get really busy though and you can’t get tickets ahead of time, so I would suggest planning around the tour if it’s on your list. This summer they also just opened up a beer garden outside with hops growing and beer flowing, it was a great place to keep the tour alive and try something different.

Enjoy the View at The Bleacher Bar

This was something we just happened upon before our Tiger’s Game. We got to Fenway early, which apparently means that nothing is open – most bars/restaurants in the area open around 3 that we saw. As we were walking though we found The Bleacher Bar underneath the stadium was open though and decided to pop in while some rain passed over. Good thing we did, as we ended up getting a table that was level with the field and had a view of the team getting ready for the game. During games they have 45 minute shifts for seats with a view, but definitely worth checking out.

Get Lost in Beacon Hill

This is the CUTEST neighborhood in the world. Honestly, it was voted one of the most beautiful neighborhoods in America, and it didn’t disappoint. Between the cobblestone streets, black shutters, and amazing flower boxes, I was sold. If you’re in the area, I definitely suggest pulling up the Zillow app as you’re walking around, it’s amazing and is a whole new level of creeping but it’s worth it. Beside the most amazing houses and beautiful landscaping there are a lot of good shops and food in the area as well. We ate at Tatte Bakery and loved it, but we also heard The Paramount was great too!

Take a Swan Boat Ride in Boston Common

For $3 you can take a swan boat around the cutest pond in Boston Common, a tradition that dates back to the 1870’s. I asked if I could just keep a tab open and stay all day, but I guess that’s frowned upon. I cannot think of a better way to spend a summer day than with an ice cream cone and cruising around on a swan-propelled boat in the middle of Boston. It was a great way to take a quick break and get a tour of the most picture-perfect park I’ve ever seen.

Walk the Grounds at Harvard

We need to go back for a longer tour and to drop off my application, but we loved spending the afternoon walking around Harvard and trying to get in to any building possible (0 was our count, not great). We did make it to the Museum of Natural History and we were really impressed with how expansive it was. It was filled with amazing finds: an exhibit of glass flowers, rock collections that would make my mom die of happiness, and lot of stuffed animals and bones that were creepy and interesting at the same time. We shopped a bit around Harvard Square then enjoyed the best pizza of my life at Russell House Tavern.


Summertime in Boston // CEO in Progress

We will definitely be back again soon, we have to catch a hockey game there, plus I know there is a lot more to explore. Have you been? Any recommendations for next time?!

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Let me know what you think!