I was eating an ice cream cone by myself in the shade of the gazebo, the cold creaminess on my tongue in direct contrast to the humid air on my arms. Gusts of warm wind came off the Miles River and over the grass lawn, reaching my face. It was my weekly Wednesday downtime, after sailing into St. Michaels with a flotilla of students and fellow instructors. Teaching sailing was a great summer job for us college students in the late ‘80s.

I smiled as I viewed the mecca of traditional boating on the Chesapeake. I was in heaven. As I was licking my ice cream and savoring the view, I saw a well-maintained black-hulled Alberg 30 sailing toward the anchorage off the Maritime Museum. As they got closer, they didn’t take their sails down. It appeared they were going to anchor under sail.

“Ballsy,” was the expression my peers and I had begun to use for skillful sailing maneuvers. Most people drop their sails and anchor under power. We only anchored under sail to teach the procedure, when the engine wasn’t working, or when we wanted to be “ballsy.”

As the Alberg got closer, I realized he was alone, sailing single-handed. And he was going to anchor under sail in a somewhat crowded anchorage. Very ballsy.

I was hooked. My ice cream was melting down the cone, and I was frozen in place.

He rolled his jib smoothly, with hardly a change in course. When he was sailing just under his mainsail, he quietly entered the anchorage. The Alberg flowed between boats as he headed toward an opening that seemed custom-made. When he approached the wider space, he pushed the tiller over, heading the bow up into the wind, and eased the mainsheet, luffing his mainsail. In this choreographed move, he slowed his boat. When he was almost stopped, he left the tiller, walked forward calmly and, when she was still, he dropped his anchor over the bow, which I could see he had already prepared on the deck.

He gradually played the anchor line out, looked steadily around at the nearby boats, and then tugged the line to make sure the anchor was set. He went back to the mast, slowly dropped his mainsail and flaked it neatly back and forth over the boom.

He went below and came back up on deck with a tan sail cover. He efficiently put it on the sail, fastening it around the mast and then under the boom, finally securing it at the aft end. I couldn’t have taught it better.

After about 30 minutes down below, he came back on deck and pulled in his matching dinghy. Yes, he’d done all of this towing a dinghy. He sat in the dinghy rowing as comfortably as he had stood with the tiller in his hand.

As he approached the dinghy dock, I was drawn like a magnet.

“Excuse me. I just watched you come into the harbor. That was the most beautiful piece of seamanship I’ve ever witnessed,” I said. He thanked me. I held the bow line while he stowed his oars. When he stepped onto the dock, I passed it to him.

Four years later, after my years teaching sailing were over, I was sailing from a mooring in the outer harbor up to a dock in Quissett Harbor on my Pearson 30. A job with a sailing organization, Sea Education Association, had brought me to Woods Hole. I had an apartment near the harbor and had sailed my boat up from the Chesapeake Bay.

I was by myself. Warm puffs of wind mixed with cold bursts from the water as I returned the solid wooden dinghy I had borrowed from the boatyard. I maneuvered through Herreshoff 12-1/2s and other gorgeous moored boats.

Judging the wind, I eased the mainsheet, nudged the tiller over, and glided up to the gray weathered floating dock. The landing was so gentle I could take my time stepping off the boat. I secured the Pearson to the faded cleats and then took the worn dinghy’s bow line from my transom and with the scratchy polypropylene in my palm, pulled her around the end to the backside of the dock.

I was “from away” to the Cape Codders, evidenced not just by the “Annapolis” on my transom but also the fact that I didn’t own my own dinghy. I had been given an outer harbor mooring where the transients were relegated. They didn’t talk to me much.

However, they did quietly watch me. And they had plenty of opportunities to watch. Unlike the Chesapeake, where you simply walked down a dock and nodded and chatted with your fellow slipmates, here you rowed to your mooring. In the hinterlands, moored well outside the inner harbor where the locals kept their boats, I rowed past them again and again on my trips to and from the boatyard. No one caught my eye or called out. At first.

That day, as I prepared to sail off the dock for my adventure on Buzzards Bay and Vineyard Sound, someone surprised me by offering to cast off my dock lines. I smiled and said, “Thanks.”