Sisters in Beantown

I’ve finally given myself a moment to sit down and write about my trip to Boston in September with my sister. Although it’s been over two months and the season has changed, I hope this post gives you enough reasons to visit the city if you get the chance.

We took an early morning Air Canada flight from Pearson to Boston Logan. Upon arrival, we realized that the airport connects directly to Boston’s public transportation system, the T, through the silver line. This was super helpful because the Airbnb we booked was in Roslindale, about a 20 minute ride southwest of the airport on the T’s Orange line.

Since this trip was my first time using Airbnb, I’ll be writing a full review in a separate blog post to follow. In the meantime, here are a few of my favourite spots in Boston:


Jamaica Plain is an eclectic neighbourhood in Boston and has a ton of fun things to explore including shops and restaurants, Arnold Arboretum, Jamaica Pond and Sam Adams Brewery.

The Arboretum reminds me of Central Park, but quieter and greener and Peter’s Hill offers a beautiful view of the city. Jamaica Pond was super quiet when we visited, but it offers canoe rentals and I hear it’s a great place to watch the sunset.

Sam Adams Brewery offers free tours for all ages (and a few free samples for 21+). It doesn’t take too much time out of the day and you get to learn about the history of Boston’s most famous beer!


One can’t visit Boston without taking a walk through Harvard University campus in Cambridge. Our trip was on the long weekend before classes started, so there weren’t many students, but a lot of tourists. (I assume this is why none of the campus buildings are open to the public and must be accessed by a university student card.)

We also picked up some Harvard merch and stopped by the Shake Shack for lunch, which is one of my favourite places to eat…ever. I highly recommend the Shack Stack which I tried for the first time in NYC’s Madison Square Park a few years ago and fell in love with.


Boston Common is part of the Freedom Trail and is absolutely gorgeous in the summer. It’s a great spot in the heart of the city to have a picnic lunch or take a boat ride. I also couldn’t help but stop for Boston Clam Chowder at Atlantic Fish Company on our walk over there. To. Die. For.


From food and drink to souvenirs to live music, Quincy Market has anything and everything. We listened to this great musical duo, Tall Heights, took a look around and picked up a few things.


Although the area surrounding Revere Beach is nothing special, it was nice to stop by the water and relax for a bit. The beach is easily accessible by the T’s blue line.


The North End is as Italian as it gets in Boston. We had dinner at Massimino’s near the TD Garden and it was great; the staff are friendly and the portions are large. We also stopped by Mike’s Pastry where I picked up a pistachio cannolo; trust me, the line is worth it.


One of the most exciting parts of our trip was the Blue Jays @ Red Sox game. I’ve been told that one MUST catch a baseball game at Fenway Park, so why not visit the city when your home team is in town? I was surprised to see so many Jays fans, and although they lost, it was a great experience and the best ending to our trip.

I’d say that our trip to Boston included a good mix of touristy things and hidden gems. Although it feels like we covered the entire city and more, I’m definitely looking forward to visiting again soon!

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