Proceed or Pass: A Tourist’s Guide to Boston

“I’m not traveling to find myself. I know exactly who I am and who I’m not. I’m only allowing the world to make me fall in love with more, more and more. -Unknown

Oh Mass., the best destination for those generally hot summer months. If you’re used to the horribly humid summer of the South-East coast, Boston is the perfect destination for a long weekend. With it being my first trip, I did all of the usual touristy stuff that I’m sure locals make fun of, so here’s my list of what to go ahead with, and what to skip.


Day One

PROCEED: Our flight got in around 8 am, and check-in wasn’t until 3 so we needed to find something to fill our day… something like alcohol. We did a 10:30 am tour with City Brew that took us around to 3 different breweries. Some may say that’s a bit early to start drinking… but it’s vacation so give us a break. It’s my understanding that every tour is different based on what day you go and what time; but on a Thursday morning it was amazing. It makes for a super long day, but we first went to Sam Adams, then went into a private tasting of Downeast Cider (not open to the public and my favorite stop of the day) — seriously I want to get this cider shipped to my house, then we grabbed  lunch at Chelsea Market and ended the day at Somerville Brewing Co.’s bar.

Day Two

PASS: We bravely attempted to walk the freedom trail, but actually never made it past the first stop: The State House, a bit underwhelming. If you want to see everything on the freedom trail, but don’t want to walk the 2.5 miles, there’s plenty of trolleys and buses that will take you to the highlights.

PASS: Then we went to the “famous” Quincy Market near the harbor, which I’d also skip because none of the food was very good. If you want to walk around and just see it, go right on ahead, then get lunch somewhere else.

PROCEED: Next came the Skywalk Observatory. It was definitely confusing to get here, as you have to walk through a mall, but the observatory gives the best views of the entire city. You can see everything from here, even Fenway Park!


UP FOR DEBATE: A short walk away is the Mapparium. An accurate-to-scale map of the world that you stand in the middle of. It’s an attraction at the Christian Science Museum, which is my only argument as to why this might be a “PASS” — during the 5-minute tour of the map they make you listen to some kind of weird christian science propaganda. If would definitely be a “PROCEED” if they kept that part out.

PROCEED: To finish out the busy day, we made the executive decision to chow down. Picture this: doughnut ice cream sandwiches; yes you heard that right. I got the lemon berry swirl doughnut with vanilla ice cream and dream’t about it for days. You can drool over these too at Blackbird Doughnuts. Then we ate dinner at Five Horses Tavern, and by ate dinner I actually mean drank pitchers of sangria and taste tested local beer flights while sitting under the warming sun.


Day Three

PROCEED: On day three, I suggest taking the ferry to a different area in Boston to spend the day. Before we jumped on the ferry to Salem, we did a tour of Fenway Park. We luckily stayed super close to the baseball field so it was an easy walk there in the morning; if you’re staying closer to the Harbor, you may need to jump in a 20-minute Uber to get there. We didn’t get the chance to see a Red Sox game, but if you have the time definitely try to do so. This field was the first ever MLB park ever built!

PROCEED: Definitely try to head out to a different area; whether that’s Salem, Cape Cod, Martha’s Vineyard, etc. — take the time to explore. We went to Salem to stumble around the tiny witch town, which included a walking tour and an amazing dinner near the water. I tried my first lobster role here at Sea Level Oyster Bar! Plus, the ferry ride back to Boston was beautiful during the sunset.


Day Four

PROCEED: Rising early on Sunday and heading off to brunch was the best way to start the day. We ate at the delicious North Street Grille. This place is super tiny and you will certainly be waiting close to an hour for a table, but it was so worth it. Their  menu is extensive: I ended up with a Pineapple Mimosa and Chocolate Peanut Butter French Toast.

PASS: Right around the corner from North Street Grille is the Paul Revere House. If your a history buff you may love to walk around this old-day shack, but if not don’t waste the time.

PASS: Then we had headed to the aquarium to kill some time before our whale watch. It’s nothing special, and if you have little kids it may be a good time consumer.

PROCEED: My favorite part of the entire trip was gong on the whale watch with Boston Harbor Cruises. It’s roughly a 4 hour trip, but we saw SO MANY whales (I’m still excited about this days later). The ride out and back each took an hour, and then we spent another hour/hour and a half seeing whales continuously breach the surface of the water. I think these pictures speak for themselves.


PASS: After the whale watch, we went on a “ghost” trolley tour. It was tacky and not super interesting. I’d skip this and get a nice dinner instead.

In all, you really can’t beat the weather or how walk-able the city is. If I could afford a summer home right now (I’m 23 — that’s definitely not happening anytime soon) I would definitely purchase one in Massachusetts. I’ll be back, no doubt about it.

Always, K.


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