Family Travel: Boston, Massachusetts

KITC would like to welcome back, guest blogger, Stephen Johnson. Stephen Johnson is an Ottawa writer who loves to write about family travel.  During the summer, you will most likely find him and his family at a local fair or festival.  During the winter, a beach in Mexico is a likely bet.  

Boston is one of the best family destinations we have ever visited.  Have a history buff in your family? Boston was the cradle of the American Revolution and has all the historic sites to prove it.   Is your son/daughter a budding intellectual? A tour of Harvard University and MIT will be right up their alley. Just want to eat great seafood.   Boston is located right on the Atlantic Ocean and has several lobster shacks that are visited by both locals and tourists.

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Here is our family’s comprehensive but far from complete guide on what to see, where to stay and where to eat in Boston.  

John F. Kennedy Presidential Library and Museum - I have always been a political junkie and amateur historian.  That is why the JFK Library and Museum was top of the list for me when we visited Boston.  The museum, as one would expect, chronicles the life and presidency of JFK.   

A visitor to the museum first starts with an excellent overview video which JFK himself narrates.  The narration is taken from excerpts of radio and television interviews.  

After the video, there are numerous fascinating exhibits including the 1960 election versus Richard Nixon, the Cuban missile crisis and the U.S space program.  The assasination of Kennedy is only lightly touched upon as the museum is meant to be a celebration of his life and legacy.   

The architecture of the building is also stunning as a full glass atrium provides outstanding views of the Boston Harbor and the Atlantic Ocean.

Our son, David, loved the museum as there are many interactive features.  It might be best visited by older children as the young ones may not find it that interesting.  

The museum is not right on the subway line but there is a free connector bus from the subway to the museum that runs every twenty minutes.  

Boston Tea Party Ship and Museum - It would be remiss to visit Boston without taking in at least one of the historical sites of the American Revolution.  Without getting into deep American history, the throwing of tea into the Boston Harbor by the colonists against the British was one of the pivotal events that led to the start of the American Revolution.  

Family Travel: Boson, Massachusetts Boston Tea Party

Set on a replica ship, the attraction does a great job of recreating the events of the Boston Tea Party.   Period actors lead visitors through everything from the town hall to actually throwing crates into the Boston Harbour.  David loved repeatedly throwing the crates into the harbour and then using the ropes to bring them back up.  

It should be noted this was not the original ship or location of the Boston Tea Party.  The ship is an accurate replica and the location is the closest they could find to the original.  

There are numerous other Revolutionary War sights in Boston but perhaps few as interactive.  

Skywalk Observatory - My wife, Sandy, said her favourite attraction in Boston was the Skywalk Observatory.  It is easy to understand why. Set on the 50th Floor of the Prudential Center building, the Skywalk offers a 360-degree view of Boston.    

A person is provided with an audio guide which adds a lot to the visitor experience.    The audio guide goes into detail about the political and social history of the city. There were a children’s audio guide and one for adults making it perfect for all ages.

The Skywalk had much more to offer than just stunning views.  There were various exhibits about Boston including the Dreams of Freedom museum which highlighted the positive effects immigration and diversity has had on the city.   

Family Travel: Boson, Massachusetts Skywalk View

I also enjoyed the exhibit highlighting Boston's sports history.  As a Canadian, Bobby Orr scoring the 1970 winning goal in the Stanley Cup struck a particular chord.  

We ended our time at Skywalk watching the two excellent videos in their theatre.  The first video did a flyover of the major attractions in Boston and the second gave an overview of the history of Boston from an immigrant’s perspective.  

Skywalk is located downtown thus is easily accessible by transit and a short walking distance to other attractions.  

Old Town Trolley Tours and Ghost and Gravestones Tour -  I feel one of the best ways to see any city is to take a hop-on hop-off trolley tour.  One of the best ones we have ever taken was the Old Town Trolley Tour in Boston. The tour covers eighteen different stops and is about two hours in length.  Both of our guides were very entertaining and informed. I was impressed the guides were able to negotiate the busy Boston streets while still providing commentary.  

The tour covers various points in the city but it is well-worth starting at the beginning to get the full experience.  

Family Travel: Boson, Massachusetts Trolley Tours

The trolley company also offers an evening Ghosts and Gravestones tour which examines the spookier side of Boston.  The tour started out with our guide donning a madman style costume that could have won best dressed at any Halloween party.  Our first stop was an old graveyard in Boston’s north end. Our guide told a number of spooky stories but also provided historical context to his commentary.   We toured several other spots with our final destination being the Granary Burying ground. This cemetery is one of the oldest in the United States and includes the gravestone of Paul Revere.  There was a suitably bone-chilling scare near the end which I will not give away.  

This attraction was very entertaining but may not be the most suitable for young children.  

Harvard and MIT walking tours -  There are perhaps no other learning institutions more iconic in North America than Harvard and MIT.    We wanted to visit both places and thought the student-led Trademark Tours was the perfect option.

We met our Harvard student guide, Emily, at Harvard Square.  Emily was entering her final year of studies. She immediately told us several amusing stories and gave us an insider’s perspective on being a student at Harvard.  We saw several famous spots including the John Harvard statue. She also showed us the dormitory where Facebook founder, Mark Zuckerberg lived.  

We wrapped up our tour at Harvard and hopped on the subway to MIT.  We met our guide, Luis, who had just completed his degree in Aerospace Engineering.  Luis filled us in on the history of MIT and some of the scientific breakthroughs that have been developed at MIT.  He also told us some of the pranks MIT students have pulled over the years including putting a reconstructed police car on top of a building.  Working siren and everything!

Family Travel: Boston, Massachusetts MIT

Where to eat - There is no denying that Boston is an expensive city.  We did find a few restaurants at a decent price and tasty food. My son’s favourite restaurant was Spyce.  He loved it because the salad bowls were largely made by robots with staff only adding the final touches.  I frankly thought it was going to be a gimmick but the food was delicious and affordable. Another favourite for the whole family was Joe’s American Bar and Grill.  The food was elevated pub food and nothing could beat the location along the water.  

It is also worth a trip to the north end where there is an abundance of Italian eateries.  We loved the pastry at both Mike’s and Modern Pastry.

Where to Stay - Again, Boston is not a cheap city.  We chose to stay out in the suburbs and take the commuter train every day.  We bought two seven day paper Charlie Cards for about $44.00.  It gave us unlimited subway rides, limited ferry transit and limited commuter train access.  It is well worth the price if you are planning to use public transit.  

For more information about Boston, visit,

Disclosure: Stephen was comped for the attractions for the purposes of this review, but all views are his own.