Tour Massachusetts Series: Boston + A Printable Guide!

What to do and see and where to shop and eat for a quick 36-hour trip to the city!

Y’all, I might just have a crush on Boston. If their traffic didn’t completely stink (and I know bad traffic– #helloimfromatlanta), I would have a full-on stalker relationship with Boston.

It’s so pretty. And old (old being a very good thing). And tasty. And full of personality.

But the traffic? Oh, the traffic makes me say bad words.

So here’s what we did: we flew in late on a Tuesday afternoon and arrived just in time for dinner. We ate fried lobster (that were the size of chicken fingers!) at Tony’s Clam Shop that’s right on Quincy Bay on the way to our hotel. Nothing fancy (hello paper plates and plastic trays), but so good.

The next morning at 9:30 we took a Duck Tour (we left from the New England Aquarium stop). It was a blast and we got to see lots of Boston–by land and by sea (well, technically river). 😉 If you book a tour earlier in the day (which I recommend for the heat alone) you save like $9 a person.

After that we grabbed lunch at the Tip Tap Room where we had the best calamari I’ve ever tasted (and we eat calamari all the time). C. enjoyed his roast beef sandwich, but I wouldn’t recommend my BLT (the olive bread was overwhelming). But I’d go back in a split second for that calamari. Like woah.

The afternoon we spent exploring Beacon Hill and Harvard Square (see the cheat sheet below for a few of my favorite shops). Both areas are beautiful, especially Beacon Hill.

Don’t these pictures just scream Boston? So pretty!

That night we had pizza at Easy Pie in Braintree. They have subs and salads too. The buffalo pizza was some of the best I’ve ever had.

The next morning we left to go to Portland via Salem. We did come back to Boston Sunday before our flight home and ate brunch at the Beehive. It was hands down the best brunch I’ve ever had–I had Belgian waffles with mascarpone and chocolate and C. had a bacon cheeseburger that was the best burger he and I had ever tasted. We sat right in front of the jazz band in the basement and it was perfect. Definitely recommend it if you’re in Boston!

And here’s my little cheat sheet I promised! I’m sure there is so much more you could do (like go to Fenway Park!), but this is all we could cram into 36 hours. 🙂

full boston cheat sheet

Click here to download my boston cheat sheet (in better resolution than the one above).

Thank you to my friends, Denise & Jessica, for her tourist insight and to my friend, Sarah, for her local insight. Y’all ladies did not steer us wrong!

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