It is a sunny, windless morning in Merchants Row, and the children aboard the Isaac H. Evans begin the day with a swim in the cold waters off Russ Island.

I remember this age. I remember coming to Maine with my parents when I was in middle school and boogie boarding atop the tight, foamy waves along York Beach. I remember asking my parents to join me in the water, but they said it was too cold; they preferred instead to lounge contentedly on the beach and simply watch. I promised myself that I would never grow so old — that I’d never pass an opportunity to swim on a warm summer day — but here I sit alongside the other adults aboard the Isaac H. Evans while the children swim blue-lipped in 60-degree water.

The adults are gathered on a housetop to match wits with a 9-piece puzzle provided by Captain Brenda Thomas. The puzzle pieces are 4-inch by 4-inch squares that must be arranged to form a contiguous pattern. It sounds easy, but it proves nearly impossible. One by one, the adults take a crack at the seemingly infinite combinations, go cross-eyed in defeat, and step aside for a fresh-thinking fellow passenger.

Captain Brenda.

We fritter away a solid hour on the puzzle before hauling lines and raising sail, but it hardly seems wasteful. It’s late August and the days are still relatively long; we still have a glut of warmth and sunlight.

The Isaac H. Evans wanders through Merchant Row toward East Penobscot Bay, then the light winds drop to a dead calm. As we rock gently in place, Brian herds the kids toward the quarterdeck. It’s time to tackle Steps 3 and 4 in the list of pirate chores: polish the cannon and swab the decks.

Swabbing, at least, has a practical purpose: salted decks resist rot, and swollen wood seals out leaks. Polishing brass, on the other hand, is purely ornamental. Nonetheless, many hands make light work, and three kids polishing a single cannon goes quickly. With the work done, each of these kids are now eligible for an “honorary pirate certificate” from the Isaac H. Evans, and free to while away the remaining hours however they see fit.

When the wind picks up, we plow down East Penobscot Bay and into the open waters of the Gulf of Maine. It was out here, in the early 1700s, that pirates sailed.

It’s difficult to find trustworthy information on pirates’ comings and goings in Maine. There are many accounts of privateers—government-sanctioned pirates—who seized British vessels during our nation’s war for independence. But accounts of actual pirates—peg-legged buccaneers with eye patches and parrots—are harder to come by.

The paucity of reliable information could be due to the old adage “dead men tell no tales.” Or it could be that there wasn’t much to plunder in this sparsely populated area, so pirates sought fortune elsewhere. However, many historians (including Colin Woodard, whose article on the subject appears here) agree that a few members of Sam Bellamy’s fleet came to Maine in 1717.

Pirates on the quarterdeck.

Bellamy, a notorious pirate of the Caribbean, had planned to rendezvous with his fleet on Damariscove Island (outside of Boothbay Harbor) in May of 1717; however, his ship, Whydah, was wrecked in a storm off Cape Cod in April. Bellamy and all hands (except two) were lost.

The other ships in Bellamy’s fleet (unaware of the Whydah’s fate) continued to Maine; the sloop Marianne made landfall at Cape Elizabeth and her crew kidnapped a local man to guide them to Damariscove. Once there, the pirates cleaned and repaired the Marianne before doubling back in search of Bellamy a few weeks later.

Another of Bellamy’s vessels, the Ann Galley, mistakenly landed at Monhegan Island instead of Damariscove. After a few days, the pirates assumed the Whydah had been lost, so they looted surrounding harbors for supplies. They sent part of the crew in a boat to Matinicus Island, who returned with a sloop, a fishing shallop, and sails from three schooners. Next, ten men aboard the stolen Matinicus sloop sailed to Pemaquid and seized yet another sloop. In the meantime, the men aboard the Ann Galley plundered a pair of fishing shallops that had the misfortune of sailing into the pirates’ anchorage in Monhegan Harbor.

During this same time, one of Bellamy’s contemporaries was also in the area. Olivier La Buse was a French pirate who’d sailed alongside Bellamy during the previous year. In the summer of 1717, La Buse detained a sloop off Midcoast Maine’s outlying islands and seized its rum stores.

Today, as the Isaac H. Evans sails out of the sprawling mouth of East Penobscot Bay, the silhouettes of Matinicus and the other outlying islands are faintly visible on the horizon.

Climbing the rigging.

When we enter West Penobscot Bay on the west side of Vinalhaven, Captain Brenda sets a course for tonight’s anchorage in Owls Head Harbor, and Trevor Bowler, an 11-year-old boy from New Hampshire, confidently steers the Isaac H. Evans for the remainder of the afternoon.

In the evening, the kids take turns climbing the rigging then participate in yet another treasure hunt. This time the pirate-themed treasures are cached aboard the ship. There’s an added wrinkle to this game: the kid who finds the most booty will earn the privilege of firing the cannon at sundown.

The winner is 9-year-old Madison Bedow from upstate New York.

The mate, Brian Thomas, loads the cannon with a blank powder charge, and Captain Brenda outfits Madison with ear protection, eye protection, and, naturally, a pirate hat. When the sun sinks below the Camden Hills, Captain Brenda gives Madison the order to fire. Madison lifts a butane torch to the cannon’s fuse, sets it alight, and runs to her mother’s side. Moments later, the cannon issues its deafening report and the nearby islands rumble with echoes.

As twilight falls over Owls Head, I talk to a passenger—a retired man from Massachusetts.

“I was worried this ‘pirate cruise’ would be corny,” he says laughing. “But this has been a lot of fun.”

He is right. For him, me, and most of the other passengers aboard this trip, a bracing swim may have lost its allure, swabbing the deck might be hard on the back, and climbing the rigging might be a terrifying. But to view these events through the prism of youth is something else entirely.

Sometimes it’s enough to simply lounge contentedly and watch.

Up next: Riding Out a Tropical Storm aboard the Nathaniel Bowditch.

Isaac H. Evans at anchor.