The Cool Girl Travel Guide: What to do in Boston

What a pretty little city.

I went on a quick couples trip last weekend and I put together a really effective itinerary to see the whole city of Boston in 3 days.

The city is basically split into sections which I’ll categorize below on my list:

Back Bay

Affluent Back Bay is a popular dining and shopping destination. Home to Newbury Street, Back Bay is flanked by historic 1800’s landmarks and well-polished locals.


Boston Public Library

The Boston Public Library needs to be on your list. It is one of the most profound historical landmarks in our country and is absolutely stunning.



Terra is inspired by earth and fire and it is located on the third floor of Eataly Boston. Everything on the menu is delicious but you must come here for the pasta!


Newbury Street

Boston’s most enchanting street filled with swanky shops and historical buildings.



Chic spot for elevated Italian cuisine. Order the mafaldine and gnocchi if you know what’s good for you.



Fenway Park

Home of the Red Sox


Isabella Stewart Gardner Museum

Hidden gem. World class art collection in this fifteenth century Venetian palace.

impossible burger


This is the impossible burger from Wahlburger’s and I was so excited to try it! The impossible burger is a plant based burger made from neuroscience that replicates the taste and texture of real meat. It was rave-worthy.



Hip vegan counter chain.


The Verb Hotel

Cool ass retro hotel. Didn’t stay here but I didn’t regret stopping by to see some rad art.

Beacon Hill

Charming cobblestone roads and elegant row homes. One of Boston’s most picturesque neighborhoods swelling with history and antique shops.


Acorn Street

Most charming street in Beacon Hill. You may have to wait in line for a picture though!


Tatte Bakery and Cafe

Cozy rustic spot serving coffee and bites.


Row Homes


The Liberty Hotel

Jail turned chic hotel that has 6 upscale restaurants and bars located right near Beacon Hill. The lobby turns into a nightclub on the weekends and the crowd was great. I absolutely loved this hotel and will book it again next time I come to Boston.

South End


Blackbird Doughnuts

THE doughnut spot. Get the chocolate glazed one and thank me later.




Cute little French terrace. Cus brunch without drinks is just a sad breakfast, right?


Niche Urban Garden Center

Cool little plant store tucked away on Tremont St.


Worcestor St

I saw this house buzzing around the internet and I roamed around the south end until I finally came across it!


I would love to know what you guys think and if you have any other cool places to add! My suggestion is to plan your itinerary in sections so you can really see the whole city in a small amount of time.

3 comments so far.

3 responses to “The Cool Girl Travel Guide: What to do in Boston”

  1. joshandevie says:

    Really like your photos

  2. Great tips!!

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