Boston on foot with Emily

One of the coolest things about Boston is that everything is walkable. Not to shit on the T, but you could do the entire day on foot. And there aren’t that many cities like that.

Do the first half of the Freedom Trail, but not the second, because like, the density of interesting spots decreases. In the beginning, you can see the Common and the Public Garden and you should definitely do that.

Then halfway, just end in the North End, where you should get a cannoli. Try both Mike’s and Modern Pastry—it’s the scientific way.

A view toward Arlington St. from the Public Garden offers  layers of architecture from different eras

Walk along the Charles. You have to see the Charles. You have to. It’s beautiful. I think it’s beautiful in the winter, beautiful in the summer. It’s what sets Boston apart from other cities. I mean, I’m biased, because I like to run. My favorite part of the Esplanade is, between the Dartmouth St. and Fairfield St. bridges, there’s that area where it splits, and there’s a little section surrounded by water.

Yeah, exactly, Gisele used to Instagram it all the time!

And if you can see a game, go see a game at Fenway. I was raised a Yankees fan, but I still think it’s the most beautiful, just incredible, baseball park in America. 

Boston's neon sunsets are best viewed from the dock on the Charles River Esplanade. They're even better if it's been a cloudy day.

Sailing on the Charles with Monica

I would do three things.

Let's say we're starting in the South End. I would go for a run and run to Cambridge from the South End, down Mass Ave. End up at Life Alive. I usually order the Goddess or the Green Goddess bowl and a Coco Alive smoothie. It’s basically like a healthy version of a piña colada.

Visit this Central Square spot for juices, smoothies, and wholesome bowls with the most delicious, garlicky sauces you (and anyone else you run into that day) will ever have the opportunity to smell.

Then I would walk to the sailing pavilion and sail on the Charles. There are a few different sailing pavilions—for BU, MIT, and then Community Boating, which anyone can do. But basically it’d just be water sports for a few hours. And if you're running or walking, you should definitely do it along the water or the Charles.

Last weekend, I went to a Berklee jazz festival. That was really cool. It happens once a year, but Berklee has a lot of concerts if you sign up for their email list or check out their website.