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Bay Tripper

Pirates of the Chesapeake: Arrghhhh!

If I am to be remembered at all in the distant future by my only grandchild, may she report to the boating press covering her solo, non-stop circumnavigation that it was her paternal grandfather who introduced her to sailing.

In July 2005, I initiated the maritime indoctrination of Claire, then 4, into the bright side of sailing, which, alas, didn’t go well. This summer I arranged an opportunity for her to experience the darker side of powerboating, but with a fun angle that would appeal to an imaginative 5-year-old. With all the pirate hoopla going on, I booked her on a small, make-believe pirate ship to test the waters again.

Before her introductory sail, I had informed her that, on my boat, she was required to address me with respect as “captain” and to respond with, “Aye, aye, sir!” and a smart salute before blindly obeying my orders. But that didn’t work. “I don’t feel like doing that,” she explained, ignoring the ancient maritime doctrine that the captain’s word is law at sea. Sadly, because of a missed nap, no wind and a powerboat chop, she fell victim to what she later described as “water sickness.”

My second attempt at getting her interested in nautical experiences came during her family’s vacation visit from their faraway home base in Pretoria, South Africa. Earlier I had presented Claire with a book, “Molly the Pirate,” which gave me a legitimate excuse to enroll her in a pirate adventure on board Sea Gypsy with a foredeck of other young children. I frequently encounter this 38-foot flagship of “Pirate Adventures on the Chesapeake” during my daysailing outings in Annapolis and rarely miss an opportunity to shout “Arrghhhh!” at them. To a child, they “Arrghhhh!” right back at me.

“I am unarmed and mean no harm to thee!” I shout back from a distance. Actually, I simply wave my white flag of surrender and leave them behind to plunder Spa Creek and the mouth of the Severn River.

Sometimes, however, when I get too close to this barge-like pirate ship and am bombarded by high-pitched squeals of “Surrender! Surrender!” I yearn to go on the attack. With that silly, childlike notion in mind, I recruited my son Scott to help stage a piratical encounter of our own to surprise Claire.

Before the adventure, we stoked her imagination with talk of pirates and especially of Molly, a role she would happily assume with full facial makeup. She accepted a forearm tattoo, but nothing else. (Her vivid imagination already allows her to operate a make-believe restaurant specializing in marshmallows and milkshakes, and to run ClaireAir single-handed as pilot, mechanic, attendant and booking agent.)

But to avoid a bout of shyness and clinging to her mother, which wouldn’t do on a pirate ship with fledgling buccaneers, I mentioned a “surprise.” Immediately, of course, she wanted to know what the surprise would be. That would have to wait, I said. Otherwise, it wouldn’t be a surprise. Get it? She did.

My bright idea was to get in on the fun and turn my sailboat into a pirate ship and stage a mock attack at sea by her “Uncle Bofus” (as she calls my son Scott) and the evil Captain Jack. Full pirate gear was rented by Scott from Backstage Inc., a Southeast Washington costume shop, and we flew two Jolly Rogers from the bow pulpit.

To attack with some degree of authority, I requested and received a letter of marque from Bob Slaff, Lord High Admiral and Minister of the Maritime Eastport Republic’s Navy, to sail under the MRE’s sovereign protection. The document was approved by “Budweiser Dave” Sells, a skinny, bearded Travelift operator and pirate look-alike at the Annapolis Harbor Boatyard. Waiting for the Spa Creek drawbridge opening and fully dressed for our encounter with destiny, Scott and I circled around a small runabout with three very young children in the bow who stared in amazed wonderment at us. We brandished our cutlasses and pistols at them and shouted, “Arrghhhh!”

They seemed stunned until their father explained, “Pirates! Pirates!” and began shouting “Arrghhhh!” in return. Soon the children were up and screaming the slogan, too, and those aboard other sailboats waiting for the bridge began to “Arrghhhh!” at us, and we returned the “Arrghhhhs!” For all I know, bridge tender Bob Scharf also was participating in the “Arrghhhh!” barrage as I motored through the opening, shouting my usual, “Thank you, Bob,” but adding, “Arrghhhh!”

Awaiting the appearance of the Sea Gypsy, we motored past Budweiser Dave on his Travelift to give him an arrghhhh-ful of thanks for his role.

The 38-foot Sea Gypsy, powered by twin 40-hp outboards, departs from her Eastport dock on several daily outings. We stood off and kept a close eye on her. I had cleared the intervention with Capt. Ruby, the handsome lady pirate who runs the operation. “Do you mind getting wet?” she asked, warning us that we would be drenched by water cannon fire as we closed in on our encounter. “Hell, no! Arrghhhh!”

We took cover behind an anchored cabin cruiser off the Eastport Yacht Club, where a hired pirate in a skiff pretended to be napping. The Sea Gypsy attacked the marooned pirate, and we headed for the mother ship at ramming speed. With Scottie in regalia on the foredeck, waving a pistol and dagger, and me at the tiller, armed with a cutlass, I began shouting demands through a speaking trumpet.

“No quarter will be given!” I shouted to the children’s feeble, high-pitched taunts of “Surrender! Surrender!”

We closed in on the tots manning battle stations at the water cannons. I shouted, “We want Molly the Pirate! Hand her over, and we will not harm thee! Where is Molly the Pirate?”

Claire/Molly waved her little hand and, quite surprised, pointed out to her mother, Betsy, that Uncle Bofus and Capt. Jack were the pirates in the sailboat. Having no pity on her loved ones, Claire manned a water cannon with the rest of the scurvy crew and blasted away, drenching us with liquid cannon shot. We chased them down off Horn Point and waved our white flag of surrender. Again, we were bombarded with streams of water.

After the ordeal, we went to lunch. Claire said she enjoyed the pirate ship and giggled over seeing her silly uncle and grandfather playing pirates.

“Can I go out on the pirate ship again?” she asked.

“Sure,” I said.

“Can I go tomorrow?” she said.

To that, there could be only one response: Arrghhhh!

For information on daily Sea Gypsy outings, visit .

Jack Sherwood is writer at large for Soundings.