The Itty Bitty Guide to Boston : Itty Bitty Itineraries

The Itty Bitty Guide to Boston

We have one word for you when it comes to Boston: Masshole. The word exists for a reason. Yes, Bostonians are a tough group, but they need to be to survive February, which lasts three and a half months. The finger? That’s just a normal greeting. Be sure to give one back. With a smile of course. While they are suspicious of fair weather friends, let it be known that Bostonians do warm up once exposed to summer temperatures and are always willing to give you a helping hand.

As a city, Boston strives to be the first – Bostonians literally started the American revolution, and they continue to be firsts in sports, tech, and learning. As a result, it’s an intense city, but there’s truly something for everyone there.

Explore the Waterfront

Boston came from the water, willed into existence by engineers who dammed the Charles and used garbage to fill in the harbor. Every once in a while, Mother Nature will try to take it back with a horrific Nor’easter and flooding, but Bostonians aren’t afraid. Their kids splash in fountains and puddles, they build amazing museums like the Children’s Museum, the Tea Party Museum and the Aquarium along the shores, and when the city seems crowded, they go out on the water. There are Whale Watching Tours, Codzilla (for older kids), ferries to the harbor islands, and water taxis just to explore the water.

Visit the Famous Fenway

You may have heard of some of Boston’s local teams. Which is why a trip to Boston would not be complete without a visit to Fenway. Look for the Green Monster, the tall green wall that was built to keep fly balls from hitting cars and pedestrian on the street. Tickets are easily purchased online via MLB or Stubhub. But if you do go to a game, make sure you know ALL the words to Sweet Caroline by Neil Diamond. Or you may be asked to leave.

Plan a Summer Evening Out

Bostonians live for summer – they’ve earned it after February – so there are plenty of events around the town that are very kid friendly, such as outdoor movie nights, Shakespeare in the park, and concerts in the Navy Yard. Every neighborhood has its own way of celebrating the summer nights so make sure to ask other parents at the playgrounds if they have any tips.

Enjoy the Intersection of History and Future

You could say that Boston’s revolutionary spirit persists in the many start-ups around the area. And also in the inordinate amount of jay-walking. Bust mostly the start-ups. In one day you could visit the house of Paul Revere, have a drink in a tavern where George Washington lunched, and then go across the river to see where robots and new tech are being developed at the MIT Museum. While you’re there, go ahead and see how much you’ll need to save up to send your kid for one year at Harvard or MIT. That’ll teach you some real fast math!

Get Lit

There is something about Boston and books. Maybe it’s all the world-class universities. Maybe it’s something in the beer, er, we mean water. Whatever it is, there’s bound to be a book your kids love that hails from a Boston author. Little Women? Boston (and Concord). Diary of a Wimpy Kid? Plainsville, outside of Boston (and he has a bookstore there). Curious George? Boston. Make Way for Ducklings? It’s only the official state book! So go ahead, go to a bookstore while you’re in Boston and check out the local author section and find some new favorites.

Itty Bitty Itineraries

More fun, fewer tantrums. Because it's your vacation too.