When the Joy of Sailing Is an Ongoing Family Question

Poor guy. He thought he had an ally.

For years, on Sunday mornings, my youngest has looked at me as my husband and older son would step outside to observe the rustling trees. As a fellow landlubber, I’ve been his only hope.

I’d give him a squeeze, watching my husband check his trusty yellow Eldridge Tide book before announcing something like, “The tide’s coming in til 10. How about a day sail to Tarpaulin?”

Here’s the thing; I’m not interested in checking the wind or hoisting the main. I don’t like being keeled over. I don’t like when our anchor rolls off the boat and we lose steering or a stay snaps in big winds.

Maintenance is a nightmare, especially on the 36-foot sloop my father-in-law built back in the ‘70s. Boat cushions are comfortable for maybe 30 minutes. Forget me steering us towards the mooring ball.

If anything, I’m a fair weather passenger. And despite my youngest being an avid surfer, I’m surprised that by now he doesn’t own a T-shirt saying “I’d rather be vacuuming.”

But I’m game to take Patience out because I love being married to a man who embraces simple pleasures and big adventures. Watching my husband sail his father’s boat through Middleground chop toward the low-lying Elizabeth Islands is viewing him in his natural habitat.

It’s a wondrous thing seeing my older son excel at first mate, grabbing lines, suggesting we fly the staysail or expertly keeping us on a tack. And it’s hard to beat the feeling of my 12-year-old snuggling up to me — a pair of binoculars in hand as he warms to the idea of being at sea, his notions that sailing is both boring and scary slipping away in our graceful v-shaped wake.

For me, sailing is mostly a way of trapping people. My favorite three people. When we’re on the boat, there are no phones, no chores, no distractions, no decisions. We can’t even promise anyone when we’ll be back. It’s just us gliding through the great emerald-blue waters of the Sound. It’s tossing a line out and catching a mackerel, spotting a giant leatherback and noticing cloud formations.

If we’re staying overnight, we’ll barbecue onboard while taking in a protracted sunset, seeing each subtle shift in color from a 360-degree perspective. Once darkness seeps in, mast lights appear from other sailboats, like tiny stars. Evenings end with cards games on the smooth Douglas fir table my father-in-law crafted all those years ago.

It’s true that no one sleeps particularly well. But, there’s nothing like dawn on a boat: climbing out of the hatch, smelling the sea-salted air and taking in the tranquil harbor, maybe paddleboarding into shore for coffee and donuts.

If we fry bacon and eggs in the wee galley, we marvel at how our improvising can make us so happy. Who knew how many times and different ways a paper towel can be used?

While at anchor, we find areas to read and nap in the tiny space of the boat. My youngest accepts his sea-salted fate and passes the time jumping off the side, lazing in a swing that hangs from the mast and scouting fishing areas. If we’re on Cuttyhunk, he’s the first one to summon the traveling raw bar via boat radio over to Patience.

My older guy, whose life is expanding at warp speed to include a car, SAT prep and a summer job, takes time to snorkel and scuba, delivering conches, along with a big smile. My husband comments on other boats (“that one’s a liveaboard” and “has that guy ever driven a boat before?”) while he tinkers about, occasionally dropping a swear word as tries to rewire a light for the cabin area. I journal, I swim, I sit back and take it all in.

Once back on land, my youngest never seems to remember how the sea wins us all over with its salty spell. No matter, because I do. If conditions prevail this Sunday, you can be sure I will say yes to the sail. Because out there on that boat, for some precious hours, it’s just sun, sea, sky, stars and Silvas.

Moira Silva is a writing instructor who lives in West Tisbury.

This article appears in July 24, 2026.