Big City, Little Time: How to See Boston in 1 Day, via the Hubway

I have good news for the on-the-go traveler who doesn’t have a lot of time: I did Boston in only one day!

Katy and friends pose with the city of Boston behind them

Obviously, if you have more time, Boston is worthy of more than just one rushed day, but in a pinch, you can do it all on the fly.  The secret is to stop at one of the 60 New Balance Hubway stations. They provide a quick and easy transportation option that will have you zipping along the Freedom Trail in no time.

The Hubway is a bike sharing system in Boston that allows you to rent bikes in one part of town and then drop them off at any one of the 60 stations without ever having to walk inside of a store, which makes it a hard deal to beat. The reliability and hassle free convenience of these two wheeled transporters, while a little on the pricy side if you’re not careful, are without a doubt a thumbs up in my book. Biking the city is also a great way to make up for all the savory calories you’ll enjoy at the great restaurants along the way!

I invite you to follow the itinerary I took on my day in Boston and nab some great ideas on scenic stops, yummy eats, and the perfect night cap.

View Bicycle tour of Boston in a larger map

We started the day on foot in South Boston with a pleasant cruise around Castle Island, otherwise known as Pleasure Bay. Although it was rather windy, seeing the city from across the bay provided views that were nothing short of breath taking. Shortly thereafter, we made our first Hubway stop to pick up our wheels and biked along the ocean to the infamous Dorchester Heights. We then went to Charlestown and rode directly to the Bunker Hill Monument, the site of the first major battle of the American Revolution, where we climbed 294 stairs to relish the invigorating bird’s eye view of the city that anxiously awaits your arrival. I won’t lie: it’s a tough trek up to the top, but the view is worth every step, and you’ll not want to skip this activity.

The View from the Bunker HIll Monument

From there we biked along the Charles River, gazing across the water at MIT and Harvard. On the left stood the Prudential Building, as well as Boston’s tallest skyscraper, The Hancock Tower. There are numerous amazing photo stops along the water here, so be sure to have your camera handy! Next we biked down “the 5th Ave of Boston”, otherwise known as Newbury Street, where a stop at Sonsie’s for tasty appetizers and one of their famous Bloody Marys was exactly what we needed to continue our voyage. Going back out to Boylston, we circled Fenway Park, where the crack of Ted Williams’ bat is still audible on Lansdowne.

Biking through the Back Bay into the Commons was an experience in and of itself, followed by a grueling peddle up Beacon Hill to the Golden Dome of the city’s capital. Cresting the top, it was all downhill to Quincy Market and Faneuil Hall, where a cold beer was waiting for us at The Black Rose, recent winner of the “Best of Boston” for Irish Pubs. Amazing live music and a top notch crowd graced the two-story pub, which proved to be a perfect night cap. It’s all in a hard day’s work, folks, but we made it happen and you can too!

Kate Erickson

About Kate Erickson

Kate is our expert on North American and Caribbean travel. She currently lives in Portland, ME, but is originally from San Diego, CA. She is an adventure-traveler extraordinaire, who finds herself in the great outdoors more often than not. With a strong passion for both traveling and writing, She pens interesting, useful and entertaining material.