Summertime often brings friends and family to Boston who, of course, want to see all the sights. It seems to me most people have heard of the Freedom Trail and put in a request to walk that famous red line around town. If you’re playing tour guide and you have kids, this can be met with some resistance. “Not again,” comes the refrain from your child. What to do when faced with this?

Bring on the pirates, I say!

The nonprofit Freedom Trail Foundation’s 90-minute Pirates & Patriots Tour is a swashbuckling affair, featuring a guy in the requisite big hat, a sack of loot, a skull-and-crossbones flag, and a working flintlock pistol. No kid can resist.

And not that you need to share this with your kids, but this is one of those happy excursions that combine getting your kids outside, exploring the waterfront, and learning something.

You’ll hear stories about pirates, privateers, conspiracies, and hijinks along Boston’s waterfront. Tour groups visit the site of Town Cove, where ships used to dock (present-day Faneuil Hall), and meander to Long Wharf, where pirates were brought to face justice, and to Griffin’s Wharf, the site of Boston’s famous “tea party.” 

Usually one lucky kid will be chosen to carry the pirate flag as your group listens to tales about Boston’s history and the American Revolution. Forget about any sort of stodgy history lesson. Guides might show off a piece of eight or how to tie a hangman’s noose, which is what pirates unlucky enough to be captured faced.

Don’t be surprised when your guide loads up a flintlock pistol and fires it into the harbor. And the next time a visitor comes to town, don’t be surprised when your kids beg to take them on the pirate tour!

Since you will end up at the brand-new Boston Tea Party Ships & Museum, you can show off the city’s latest museum, an interactive and entertaining site. Read more about that museum and other harborside attractions for families in a previous post here.