Highlights from Boston

It can be hard to find things to do in a metropolitan city sometimes, especially being from Chicago where I get that kind of vibe already. But Boston had it’s own unique charm with a small city feel. The cobbled stone streets with the smaller alleys gave off a European feel to it which I adored. The city is not too big and you can get a lot done in the time being but I narrowed down some highlights for you to check out.

Charlestown and the Freedom  Trail

Charlestown is a historic waterfront neighborhood perfect for those that want to be close to Boston, but not in the hustle of it all. Make sure to go down by the marina for a picturesque view of all of Boston. Better yet, check out Pier 6, for some delicious cocktails and waterfront views.

Parts of the Freedom Trail are also located in Charlestown. The 2.5 miles trail is lined with 16 significant locations running through downtown Boston. The 1797 U.S.S. Constitution warship and its museum are in the Charlestown Navy Yard which I found was a good spot to start your trail. To ensure you stay on the trail the whole time; follow the red-lined path on the sidewalk.

photo (8)photo (7)

Faneuil Hall

One of the stops on the Freedom Trail; you will find 3 historic market buildings as well as tons of restaurants and shops. Be sure to check out the famous Cheers Bar for a drink or some food.

photo (3)

Newbury Street

Perfect for some shopping and restaurant hopping. The street is super enchanting and makes you want to move right into one of the houses.

photo (4)

North End

This was probably my favorite area, just because I LOVE Italian food and Italy in general. Th cobble stone streets and smaller alleys made me feel like I was transported back to my days of studying aboard in Florence. Filled with plenty of restaurants and also part of the Freedom Trail, this area is a must see. Make sure to check out Mike’s Pastries because the cannolis are to die for.

photo (6)

South End

This is the place to go to hit up the bar scene, especially for the mid 20s and up. There are a couple bars in the area that are walking distance, so perfect for some bar hopping. The food is pretty good as well! Try the pizza at the Lincoln Tavern and Restaurant and go watch your favorite sports team at Stats Bar and Grille.

Fenway Park

Now this is a classic. Everyone who knows baseball knows this is one of the most iconic stadiums. I recommend going during the spring/summer season because there is not a whole lot to do during the day around there during the off season. Once it hits the darker hours, the bars do come to life. Keep in mind that this is more of a younger crowd, so if you are not looking for that kind of atmosphere, I would recommend getting your drink on elsewhere.

photo (5)


Stepping onto Harvard’s campus was like stepping into a fairy tale. The architecture and the fall colors made the campus feel magical. Feel free to venture out around their campus and check out all the different buildings. I would suggest going on the weekend when the students do not have classes because it is less crowded and easier to maneuver around without feeling like you are in everyone’s way.


Seaport District

Filled with awesome architecture, a vibrant art scene and picturesque views of the waterfront. This area is great if you want to be near the water and do some shopping and check out some art. I highly recommend going to Legal Harborside. It offers three different dining experiences and provides magnificent views. I checked out the first floor for more of a casual dining experience, but which ever you choose you cannot go wrong.

photo (1)

Who else has been to Boston? And what are your favorite parts of the city? 🙂

Happy Travels – xoxo Dre ❤

Posted by

Just a girl living out her dreams of traveling the world.

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.