24 Hours in Boston

Welcome to Boston! This glorious location is not only one of the oldest cities in the United States, but it's easily the richest in history.Retracing winding roads to find where we as a country began is exhaustive, to say the least. If you have come to do just that, or if you have the privilege of being stationed here, you may need a tour guide that knows it as home. But, even if you only have 24 hours in Boston, you can still learn an awful lot about this great city. Allow me to share the best tips that'll help you get the most out of your visit.

Where to Live or Stay

First and foremost, Bean Town is pricey. The cost of living here is on par with the most posh parts of our country. Surrounding Boston are areas of higher and lower income intertwined. Sam Adams was a man of little means, though that did not stop him from interacting with Paul Revere. To this day, that dynamic persists.

You will not find suburbs here—only higher and lower priced zip codes surrounding the city, continuing out like a spider web. If you're moving here, you'll want to check out places in the South Shore. If you're vacationing here, your best bet is to use Airbnb. Once you have figured out your sleeping arrangements, it is time to explore.

Checking Out the Town

Photo by    Jorge Cancela

Photo by Jorge Cancela

Do not rent a car unless you want to visit other states while you are here. Boston has the oldest and most convenient subway in the country. Plus, military ID holders ride for free! That’s right bud, you ride for FREE!

Now, allow me to introduce you to our dialect. We don’t mean to be brash—we're just direct!  Do not get easily offended, because we don’t. And for an added bonus, say it with me: "Bas-ton."

All things start in the center of New England towns called the Common. From here, you can go anywhere in the town. As fate would have it, this is where Mr. William Blaxton first settled.

So let's go! Follow me on the Freedom Trail, and you won’t get lost.

There are several ways to experience our history, but it is a trail of bricks starting at the Common that leads you to the most significant places of that history. You can leisurely stroll the path with a Youtube guide, try and grab a townie (I don’t suggest this) or you can run or walk it with tour guides.

The trail is less than three miles long and loaded with historic locations. You will see the gravestones of John Hancock and Mary Chilton, stand on the spot of the Boston Massacre, glean the outside of the oldest tavern in Massachusetts, and run up Breed's Hill to the statue of Colonel Prescott.

If you’re feeling hungry at this point, let's grab something.

Chowing Down

Photo by    Paul Sableman

Photo by Paul Sableman

Starting in the North End, Carmelina’s is a great place to experience savory Italian. If it’s a weekday, you should stop into Sam Lagrassa’s for a sandwich, located one block away from the Common. Need a drink? Stop by The Green Dragon Tavern and sit where our forefathers made small talk. Want to have a beer and visit the oldest ballpaak in the country? Stop into the Yard House just two blocks from Fenway. I heard you trying to pronounce that like a townie—good job! Just don’t over do it, you.

Right and Up tip: Tours of Fenway Park are available year-round. Be sure to ask about the military discount, as tickets are $3 cheaper than regular price.

Understanding our history is an essential part of coming to Boston. Once you have walked it, you will forever know where you are. So, find a cozy place to relax, have a few drinks, eat some wicked food, and enjoy yourself in Boston.

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about the author

William Nightingale is from New England and is currently stationed in Boston. He has enjoyed a 15 year career in the military, serving in the Vermont Army National Guard, the Air Force, and now as an artilleryman in the Army. He has been a skier for over 30 years, but that’s a story for another time.