Boston skyline.
The view of the Boston skyline crossing over a bridge from Cambridge to Boston while running along the greenway trail system.

Pun totally intended. I was in Boston last week for a few days and did an interview for the blog with my friend Heather (read that here) before she raced the Boston Marathon. The main point of the trip was to cheer on my friend in the most famous marathon in the world, but we absolutely made the most of our time in this beautiful city, and I wanted to share my thoughts on what we comfortably squeezed into a few days. Here’s a look at what to do in Boston!

Copley Square, Boston Marathon Finish Line.
Strolling around Copley Square a few days before the Boston Marathon.

We stumbled into a t-shirt shop we thought was going to be a bakery and went out to the fanciest dinner of our lives wearing river sandals… Heather had on socks with hers. We may have screamed “tourist” but you know what? That’s okay.

This isn’t everything we did, only the things I think you should consider adding to your itinerary.

Waterfront Boston.
Playing with Heather’s mom’s lensball while walking around the waterfront not far from the Freedom Trail.

Newbury Street

This beautiful street near the heart of the city offers options for dining, entertainment and shopping. We ate at Sonsie’s for brunch one morning and grabbed some gelato while making our way down the crowded street (which I highly recommend). There are several well known brands with store fronts like Fjall Raven, Patagonia, Arcteryx, and more (of course I only remember the outdoor brands). There’s also the cutest book shop I’ve ever seen combined with a coffee shop/diner that I will definitely be making a point to return to.

Trident Booksellers and Cafe.
Snagged my brother a signed copy of Ryan Hall’s new book from Trident Booksellers and Cafe.
Amorino's Gelato
Amorino’s rose-sculpted gelato topped with a gelato filled macaroon.

Freedom Trail

I believe this walk gave us the best snapshot of the city. It offers the perfect blend of the incredible history found in this city, beautiful views and sweet treats. We didn’t walk the entire thing (Heather had already covered PLENTY of miles) but we did cover a significant portion and diverge from the path a bit in order to get views of the water.

Boston Public Garden

This was my final stop before dinner on the eve before departure. This park is a beautiful place to stroll, lounge for the evening, or snap the perfect commemorative picture.

Restaurants

Here I need to give a big shoutout to Heather’s parents for always taking me in as their own child and treating me to delicious meals over and over again. On the last night (at the real fancy restaurant) I mentioned wanting to pay for my own meal and Heather’s dad asked me why. “Because I’m an adult…” I said sheepishly. “Hold on. Let me say that with more confidence.” I paused “I am an adult,” I said firmly.

“An adult that’s about to be un-employed,” he smirked.

Touche.

Boston Chops Steakhouse in downtown Boston.
Walking into the fanciest restaurant we’ve ever been to and Heather is wearing Sockos… I’ll be telling this story for awhile.

I am so thankful for Heather’s friendship. I’m equally grateful for a family that has taken me in as one of their own. The relationship her parents have inspires me to work hard in my own and makes me want to take pictures of them holding hands and crossing over a beautiful bridge… yeah, I made them do that.

Here’s my top three picks for dining:

The Friendly Toast

Spunky and full of color, this breakfast spot offers something for everyone.

Boston Chops

We knew this one was going to be fancy but when we arrived at the big red door wearing our Chaco sandals and exchanged wide eyes after observing the menu I decided this meal was going to be more than food: it was going to be an experience.

Cantina Italiana

This one we expected to be super fancy. However, instead of feeling underdressed we walked into the most homey, jam-packed restaurant on the block. I’m glad we had a reservation because many runners seemed to have the same thought we did about carb-loading before the race.

I can’t wait to return to this city again in a few months and again next year to explore more of it before my own chance to run the Boston Marathon. Ever been? Tell me what I must see below!

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