What to do in Boston, MA

Whether you are looking for a slice of American History, great food, or adventure on the bay, Boston is filled with everything you are looking for.

While walking through downtown Boston recently I suddenly came up an enormous sailing vessel at the city’s Fan Pier. Eager families were lining up for deck tours, and Instagramers clambered for the best selfie angles. It reminded me that there is always something happening in this storied city, and that it is well worth a trip with the family.

Boston: Birthplace of the American Revolution

Nestled in the protected confines of Massachusetts Bay, Boston is often referred to as the birthplace of the American Revolution. Yes, there are older cities and towns. Several English settlements predate the Massachusetts Bay Colony by over a decade. And yes, the Constitution and Declaration of Independence were signed elsewhere. But when you consider the volatile series of events during the 1770s that culminated in the signing of the Declaration of Independence, Boston was cataclysmic.

From March 5, 1770, when British soldiers fired into unarmed demonstrators outside the British custom house, killing five civilians, tensions increased dramatically and set the stage for American Secession. There was no place more on the front lines of the American Revolution than Boston, and the history present in the city is easy to see and explore today.

Freedom Trail Boston

Paved in Red Bricks, the Freedom Trail winds it’s way through 2.5 miles of downtown Boston, visiting 16 historic sites. From the Old Corner Bookstore to the USS Constitution, the Freedom Trail allows you to walk the steps of American History. There are a wide variety of Freedom Trail Tours available, from a basic walk through the major historic sites to the “Historic Pub Crawl”

Get Your Boston National Park Junior Ranger Badge

There are 8 National Parks located in the Greater Boston Area, with 3 located in Boston proper. As a family, earning Junior Ranger Badges is a fun way to learn about the history and/or natural surroundings of any place that we go.

One of my favorite sites to visit is the USS Constitution. She is the oldest commissioned ship in the US Navy. Known as “Old Ironsides” she was seen as nearly indestructible during the War of 1812. After an extensive restoration from 2015-2017, she is in prime condition, and an amazing representation of a fighting ship from the age of sail. Also located in the Charlestown Navy Yard is the USS Cassin Young, a WWII era Destroyer, and the parks service has a mobile app that allows you to explore her history and WWII in detail on your phone.

You will need to visit 5 of the historic downtown sites to earn your Junior Ranger Badge, but with Bunker Hill, The Old South Meeting House, and the Paul Revere House within easy walking distance, this in not a difficult task to accomplish. And the amount of history involved in such a small area is simply astounding.

And while you are walking through history, visit the Boston Tea Party Museum. You’ll even get to throw a bushel of tea into the harbor!

One of the most unique ways to see Boston is on a “DUCK” tour. These WWII style amphibious vehicles will offer you a guided tour of downtown, before driving right on into the Charles River for a view that you can’t get anywhere else.

Get out on the Water in Boston Harbor

If your taste of the water on a DUCK tour doesn’t satisfy your nautical ambitions, Boston has you covered. The city of Boston was settled largely due to it’s well protected harbor. Perfect for shipping, fishing and with two major rivers allowing for the transportation of goods inland, Boston quickly became a major hub of American commerce. That same harbor is an amazing place to head out onto today. The protection afforded by the surrounding islands keeps the waters relatively calm in any weather, and there are always sights to see.

There are numerous operations offering sightseeing sails out of Boston Harbor, and all of them are worth checking out. If you happen to be catch them in town though, you should sign up for a sail on the Schooner Roseway. Herself a designated National Historic Landmark, she has a long history in Boston, first as a fishing vessel in the 1930s, a patrol boat during WWII and finally the last sailing pilot vessel on the East Coast, bringing pilots out to guide ships into the harbor until 1972. Passenger sails and events in the harbor are available on select dates. Roseway also spends much of her time bringing students out for the most unique educational experience of their lives.

Harbor Islands and Beyond

Trips continue out past the confines of Boston Harbor as well. There are numerous trips available out to the Harbor Islands, as well as into Cape Cod Bay. If you are looking for a wide variety of experiences, Boston Harbor has everything that you are looking for.

Islands of Adventure

The Harbor Islands are, wait for it, a National Park! You can go camping, head to the beach, even volunteer your time to help maintain these jewels of the harbor. There are a myriad of activities availabel, and if you are looking for a quick way to forget that you are even in a city, this is it. You can learn more about the Harbor Island Parks here.

Thar She Blows!

Many coastal cities offer Whale Watch trips, but the numbers and activity of humpback whales on Stellwagon Bank is not surpassed anywhere that I have been. To get out there fast from the city, Boston Harbor Cruises has an impressive fleet of high speed Whale Watch vessels that will get you more time seeing whales on your trip.

Eat in Boston

So, I can’t go anywhere without trying some of the local cuisine. Boston is no different, with a wide variety of selections, from Seafood to Italian to Asian, you can’t go wrong in the city.

I love seafood, and I always will have a soft spot for Italian. One of my favorite Boston eateries is the Daily Catch. Their location on Hanover Street in the North End is cozy and intimate. Their food is always amazing, blending local seafood with traditional Italian recipes.

And if you are looking for the perfect pastry in Boston, Mike’s is the place to go. Located on Hanover Street, and referred to as “home of the cannoli,” hungry visitors have been flocking to Mike’s since 1946 to satisfy their sweet tooth.

There are also a wide variety of restaurants in the seaport district, food festivals, and some of the best food trucks you’ll run into in downtown.

Boston is a city filled with things to do, and it is hard to touch on them all in one post. Other worthwhile family friendly stops while in town are;
Boston Children’s Museum
New England Aquarium
Boston Museum of Science
Fenway Park – Go Red Sox!

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