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Home  >  Destinations • North & South America  >  48 Hours in Boston
DestinationsNorth & South America

48 Hours in Boston

Siobháin Spear September 14, 2019
Sunset over Boston from the top of Beacon Hill in Massachusetts

You can get from New York City to Boston in just over 4 hours on an Amtrak train, so we split up our trip to the States by sandwiching a 48-hour trip to Boston in between our 5 days in NYC.

Eliot Hotel in Back Bay

What I’ve learned about my travel preferences over the years is that I love staying in boutique hotels; they ooze character and they’re all about the details. Upon arrival in Boston train station, we walked to Eliot Hotel, where we based ourselves for two nights. The Eliot Hotel sits along a picturesque boulevard in Boston’s Back Bay neighborhood and is an ideal for location for anyone wanting to explore Boston for a weekend. The rooms exude a timeless elegance and bring European city vibes to the heart of downtown Boston, so we welcomed the plush change from the box-like rooms in central New York City.

A Trip to Fenway Park

Red bleachers and baseball pitch at Fenway Park on a rainy day in Boston Massachusetts

Fenway Park, home of the Boston Red Sox, was high on our priority list for our 48-hour trip from NYC to Boston. Unfortunately, there was no game day while we were in the city, so we opted for the stadium tour at Boston’s home of baseball instead.

Since there was no match, we decided to improvise our own pre-match experience, so we grabbed some pizza and nachos in the nearby GameOn Bar and then took a trip to Bleacher Bar, which is a converted batting cage that has become one of the world’s best sporting bars with a view directly into Fenway Park Stadium through a large caged window. Grabbing a Samuel Adams at a high-top table here is an awesome experience that’s probably all the better just before a big game.

We took the stadium tour of Fenway Park during a rainy day, but for the majority of it, you are under sheltered areas, so it doesn’t really make a difference. It’s easy to see how America’s oldest baseball stadium is also once of its most loved sporting arenas. We got to see all aspects of the stadium and the famous “lone red seat” that marks the longest home run in Fenway Park when a baseball hit a guy in the head back in 1946.

Sonsies

Sonsies will always be special to me for serving up one of the most delicious breakfast dishes I have ever eaten. We walked to Newbury Street and ate the ‘Boston Best Sandwich‘ at Sonsies on the second day of our trip. At the end of that same day, we returned to Sonsies for cocktails when it was very much alive with atmosphere and smoked Old Fashioned cocktails. A walk down Newbury Street will give you a glimpse at eclectic boutiques and the 19th-cenury houses that line the mile-long road.

Boston’s Graffiti Alley

Girl with little red backpack walking through Graffiti Alley in Boston Massachusetts

After breakfast, we got ourselves back onto Massechussets Avenue to cross the bridge over Charles River and take a walk around MIT; it’s a cool, urban campus that gives you an insight into the world of students with a 4.16+ GPA. Following on from that, we walked through the Cultural District of Cambridge, which is where we stumbled upon Graffiti Alley in Central Square. This is the only place in Greater Boston where graffiti artists can express ideas without worrying about getting arrested. There’s a a colourful canopy roof, and you’ll likely come across an artist in action.

Bartley’s Burgers

The USA's best burgers in Bartley's Burgers, famous for all the celebrity visitors near Harvard.

Just before lunch, we continued our walk to the Harvard University Campus for another Ivy League lookaround; the old stone buildings and the park-like feel make it a popular stop-off for tourists who want to check out Zuck and Obama‘s former campus.

A friend who had studied in Boston told me about Bartley’s Burgers which sits just across the road from Harvard, so that’s where we headed for lunch. The burgers and the frappes were delicious; it’s easy to see why the Wall Street Journal voted Bartley’s as one of the best places for burgers in the U.S.A. As well as hosting a plethora of celebs in its time – Johnny Cash, Al Pacino, Shaq O’Neilll, Adam Sandler, Tyra Banks and more – what I loved more was the punny menu. I mean, why wouldn’t you want a ‘Siri-ously good iPhone burger’ for lunch? The witty wall signs, celeb memorabilia and retro style of this burger joint add to the overall lunch atmosphere.

Boston Common & The Freedom Trail

Girl with little red backpack walking through Boston Common in Massachusetts

After grabbing a bite at Bartley’s, we caught the subway from Harvard Square towards Ashmont and jumped off at Charles Street – across the river. If you walk through Charles Street and Beacon Hill, you’ll end up beside Boston Common, which is the central park in Downtown Boston. The 50-acre park is a relaxing escape from city life, but it’s also central to its history. The park forms one of the stops on The Freedom Trail that tracks 250 years of history and 16 significant landmarks.

Cheers Bar in Beacon Hill

Cheers bar on Beacon Street in Boston, Massachusetts

Just across the road from Boston Common, we came across the famous Cheers Bar, which is the pub that inspired the well-known TV sit-com (I recognised the sign, but I can’t say I ever watched the show!). If you head down the steps under the sign, you’ll find yourself in the basement bar where you can have drinks or purchase souvenirs if you’re a fan of the show.

Warren Tavern

The famous Warren Tavern pub; the oldest pub in Boston, situated in Charlestown and dating back to 1780

Exploring Charlestown was fun; we went in search of the oldest pub in Massachusetts and when we found it, we stopped for drinks. Warren Tavern was first erected in 1780; both George Washington and Paul Revere drank at this watering hole, putting the Charlestown tavern firmly on the map.

Chasing Charlestown sunsets

Colourful houses and uphill street in Beacon Hill, Boston Masachusetts

The Charlestown neighbourhood of Boston is home to many cosy streets lined with colourful houses that ascend towards Bunker Hill, another stop-off on The Freedom Trail. The Bunker Hill monument at the top marks The Battle of Bunker Hill between the Americans and the British back in 1775. You can climb the stairs to the top for an incredible view over Boston, but the last climb is at 4.30pm and we arrived at 4.50pm so missed the chance. However, the sunset view over Boston was worth watching from Bunker Hill.

Exploring Quincy

Quincy and Charlestown bridge with city lights at night

Quincy is a socially and culturally vibrant district of Boston that’s worth exploring. We ended our evening in Quincy Market, where foodie hangouts and artsy stalls occupy the three main buildings. Bars and eateries are plentiful in the area, so you can easily plan a bit of a pub-crawl or a good night out; expect multiple Irish bars and Irish residents around the area and the entire city. We stopped off at Hennessey’s Bar and The Black Rose before heading back to the Back Bay area for our final night in Boston.


New York or Boston – which city would you choose?

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Fusing a love for travel with a passion for storytelling, Away With Words was brought to life by Siobháin Spear in 2018. Siobháin is the Editor-in-Chief & Co-Founder of insydo, a regional lifestyle publisher; she is also a Co-Founder of Brand Ripplr, the region’s largest influencer platform.

Having met many talented globetrotters while clocking up her 56 countries, Siobháin opened up Away With Words to the digital nomads of the Middle East – those worldwide wanderers who take full advantage of living in one of the fastest-growing travel hubs on the map. Born out of a passion for exploring the globe and creating infectious content, Away With Words is a meeting of creative minds from across the World (Wide Web).

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