When little kids learn to sail, it’s like riding a bike. They just keep getting on and trying. Finally, there’s one single moment in time, when they “get it”. But what would it be like to learn to ride a bike, for the first time at 50?

Those thoughts went through my mind last weekend when instead of rowing the dinghy to shore, my wife said, hesitantly, “Leave the sail on, I think I’ll try to sail over to Cabot Cove”.

I was surprised, I wasn’t sure she could do that. She’s been very busy for the last 25 years that we’ve been sailing together.

Not wanting to spoil the moment, I suggested she aim for the beach on the other side of Pulpit Harbor, try to make the masthead telltale stream aft smoothly(she has that in this photo), and gave her a good hard push in the right direction. I had the odd deva vu feeling of running alongside my son or daughter on their first 2 wheelers.

She did ok, reached the other side of the harbor, and tacked in the direction of the cove, to windward. But she was wobbly now, and the dinghy began to slow down. About half way there, she was nearly dead in the water. The sail was full but sheeted in tight and hopelessly stalled. She was aimed at Cabot Cove,… but she was going nowhere.

If there was a moment when you finally let go and the rider awkwardly peddles away, this was it. Would she finally “get it”, or pack it in and ship the oars and forget the whole thing? At that moment, I was riveted on the foredeck.

Then a break. A Dark Harbor 20 tacked in front of her. It pinched up to windward, and headed toward the cove entrance. Would she take the cue from the boat?

She did! I saw the tanbark sail shutter several times as she let the sheet out to mimic the sail angle on the boat ahead. I could see in the distance her hat flashing as she looked at the masthead streamer(see that in the photo?).

She must have fallen off a bit, because the dinghies bow lowered as the wind attached, and she began to speed up in the wake of the DH20. Soon after, her tanbark sail disappeared into the granite entrance to the cove.

I was exhilarated and went below to do the morning dishes. She came out of the cove a half hour later, back under sail! She had de-rigged, rowed to shore, re-rigged, I was impressed.

After one jibe to windward, she settled onto a broad reach, making sail adjustments along the way, aimed directly for our boat. Steering at the approaching counter(as she’d seen me do a zillion times), at the last moment, she pushed the tiller to port and enjoyed the way a dinghy stops near instantly alongside.

The dinghy rub rail lightly kissed the topsides. She can sail.