JC Lightcap a RoamRight Blog Author

Enjoying The Best of Boston In A Couple of Days

The last time I was in Boston was for a layover from Quebec, Canada to Lincoln, Nebraska in 1999. I went into to town to get a present for my mother, and I remember three things: 1) How easy it is to get to town from the airport, 2) Boston is an incredibly walkable town, and 3) I almost missed my connection TWICE.

What Makes Boston Great

I arrived this time to find that Beantown continues to grow while keeping intact many of the things I had loved about it from years ago. Since 1999, Boston has seen a huge surge in the medical, biotech and solar industries, with the technology companies following closely behind to facilitate. The completion of the Big Dig in 2002 moved several main highways underground, installed a new bridge, improved access to the airport and made way for new green spaces in the city. Gentrification followed, with housing prices rising as fast as the number of awesome restaurants blocks away from gorgeous, renovated brownstones. At this point, there are so many people relocating to Boston that you would be hard pressed to find anyone who can properly say "Pahk the cah in Hahvahd yahd."

When I found myself back in Boston this year two days before the start of a weeklong seminar, the first thing I was reminded of was how walkable the city is. Showing up early to get intimate with the city was the best thing I could have done. The second best thing I did was to take a running tour. Boston is (obviously) packed with history; the City Running Tours guide for our group pointed out facts and historical trivia while keeping us out of the shadier parts of town. The best part? I got a great workout at the same time! Every day after the conference let out, I wandered around and explored, only to realize that the déjà vu I was feeling was because I had been here on the running tour days earlier.

While walking was great once I was downtown, I have to applaud the MBTA’s public transportation system for making Boston so easy to navigate. The arrival from the airport was quick and much cheaper than a taxi. My walk from baggage claim to the Silver Line shuttle was maybe 45 seconds, and it had me across the river and into Boston Commons within 35 minutes. The best part of this service though is that it’s free. In general, most shuttle and bus stops are equipped with monitors updating arrival times. Some stops even have an overhead heater, an especially nice feature if you are visiting in January.

What to Do in Boston


A quick Internet search will result in multiple guided opportunities to tour the city. I’ve mentioned City Running Tours already, but what if you don’t feel like a group tour? Boston has you covered. The Freedom Trail, a paved yellow brick path (okay, it’s normal red bricks), follows the major historic locations throughout the city.

Other Favorite Tours

The Harpoon Brewery tour

Take a tour of the Harpoon Brewery, where you’ll see the very first liquor license issued in the state of Massachusetts since Prohibition. Show up early, or be prepared to wait in a long line; try the pretzels. Harpoon is located on the Boston waterfront, an area known for the shiny, glass-windowed buildings. Those glass buildings may contrast sharply with the original landscape on the waterfront, but not to worry, they’re being put to good use.

The Red Bull Cliff Diving Tour has made a stop in the Boston waterfront multiple times in the last few years. The cliff, in this case, is the rooftop of the Institute of Contemporary Art. (Coolest. Idea. Ever.)

Food tours

Check the Internet for food tours of Boston’s Back Bay and market district. For phenomenal seafood, Italian and cannolis, head to the North End of town. The once-seedy Chinatown area is now clean, safe, and will satisfy any urge you may have for Chinese, Malaysian, Japanese hot pot, Thai and bubble tea.

Living History

Boston is a history buff’s idea of the perfect vacation: It’s the home of Paul Revere, the Boston Tea Party, and Sons of the Revolution, and landmarks like the Green Dragon Tavern and the Bell in Hand only add to the experience. After just a couple of days of exploring the city and visiting the historical sites, I realized that Boston is much more than just going from site to site and taking pictures. It is one of those cities that has a great personality, whose transplant residents serve as fiercely proud ambassadors of the city as much so as those born and raised there.

Do not miss out on Boston due to delays or hiccups in your travel plans. I almost ruined my trip by missing my connection, and I did not have travel insurance. Make sure you invest in travel insurance before you go so you have the peace of mind to settle in, hang out, and soak up all uniqueness that Boston has to offer.

Fun is part of any travel experience, but so is staying protected. Learn more about our policies here!

Note: Available plans and coverages may have changed since this blog was published.


About the Author

JC Lightcap

JC Lightcap, a RoamRight Blog Author Former travel disaster, now a serial traveler, travel safety advisor, and author of The Travel Safety Handbook. Poster boy for learning from others mistakes. Now I provide travelers with the tools to focus on their travel goals; I advise business travelers,prepare study-abroad students and equip families with the knowledge to return home successful with memories that will last a lifetime, not horror stories. Follow JC on his blog at Travel-Safer.com, on Facebook, or on Twitter.

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