Think of "Good Will Hunting" and "The Departed" and you've got a sense of its grittiness. Think of JFK and you've got the typical Bostonian accent. And think of Harvard and MIT and you've got a sense of the student vibe.
But as well, there are waterways and green spaces aplenty and it was the location of some of the most important moments in American history.
Leaving Bessie in Salem, we caught the commuter train in and walked over to the Science Museum to hop on one of the famous Boston Ducks.
While poking our noses in at the Science Museum, we came across the Live Animal Care Center in the basement and said hello to a couple of tortoises, a grey squirrel, some snakes, a duck and other cool creatures.
On board our 'Duck' we cruised around the streets of Boston, checking out the sights downtown while learning a bit of the history from our driver Guido Gondolier.
As we thought it would be, the boys' favourite part of the tour was when we descended down an embankment and splashed into the water to cruise along the Charles River.
What we didn't realise was that Guido would offer up the chance for the kids to drive the Duck.
When Guido asked Indy what he wanted to be when he grew up, Indy answered that he had wanted to be a race car driver but had changed his mind because he was worried the police would catch him because he didn't have a licence. Oh, the worries of youth!
Poor Guido couldn't get either of the boys to stop talking - the chatterboxes strike again!
After our fun time on the Duck, we found a playground before catching the "T" subway to the Old State House for a quick stroll to Quincy Markets.
After some lunch, we checked out the busy harbour front and the kids had a ride on the most gorgeous carousel - the Greenway Carousel - which features exquisitely crafted creatures from throughout the region.
We strolled along the Freedom Trail to take in the historical sights, including the site of the Boston Massacre, the Old South Meeting House and the Granary Burying Ground.
When we reached Boston Common, the boys launched themselves into the playground beside the Frog Pond, making friends with some local boys.
Little did we know when we entered the subway for our next destination that it was going to be one of the squishiest journeys ever.
We've been on a lot of subways in our time but this trip was a doozy, second only to the time in Paris peak hour when a pervert had grabbed me and I couldn't even move my arms to smack his hand away.
It's little wonder it was so busy - we were travelling to Fenway Park on a game night!
And so the four of us came to be sitting at baseball's hallowed ground, watching the famed Boston Red Sox take on the Detroit Tigers.
Great atmosphere!
I loved hearing the theme songs each player had whenever they came out to bat or they hit a home run or made some great fielding play.
With the kids close to nodding off, we had to call it quits before the end and made the return home on the "T" and the commuter train without issues.
Incidentally, the Red Sox beat the Tigers 20 - 4.
The next morning, a little weary from our late night out, we left Salem and drove to Concord to visit the Minute Man National Historic Site.
The multimedia presentation there is brilliant in transporting you back to April 1775 when the first shots rang out in the American Revolution and Paul Revere and William Dawes made their famous rides to warn the local militia who were ready to fight at a moment's notice (hence "minute men").
