I’ve developed a reputation among friends as a sailboat matchmaker. It often begins with an irrational text message: “I found an amazing boat. Almost free. Needs work. I should get it, right?”

Our team—sailing on our midsized boat—has experienced both sides of the looming wind-shadow debate. This is when a big boat in Division 1 is about to overtake a smaller boat in Division 3, and the

Five adult sailing students were making their way back to the dock after a couple of hours of drills on a J/24 and two instructors and I were following in a tiny chase boat. We were heading into the �

Since sailors are now flying, sail trimmers are now biking and cloud computers are now navigating, it seems appropriate to separate today’s sailing myths from reality. Surprise, everything I’ve li

Interest in sailing saw a remarkable uptick starting in about May of 2020 that hasn’t let up. Google searches for the phrase “How to sail” had been increasing steadily since 2004, but doubled du

Golf course greens turning tan. Ski jumping off of artificial turf towers. Scuba diving on monochromatic reefs where rainbow coral once grew. Mountaineering to peer into one last crevasse. Climate cha

Every spring we assemble our crew lists for the season and pack key sailing events into our best friend’s calendars. We draw a Venn diagram of teams to race on weeknights and weekends (since not eve

Vesper’s giant carbon fiber rig towered over the rest of the boats in the yard like Kareem Abdul-Jabbar visiting a kindergarten classroom at nap time. The TP52 glistened in perfect glossy shades of

Our local fleet champ recently declared that he’s done with sailing. “This is it,” he said. “When this sailboat sells I’m not buying another. Runabouts don’t have runners.” He’s a ter

Whenever a newcomer comes to town I usher him or her to our priceless waterfront and we talk sailing. If I see even a flicker of curiosity, I suggest sailing lessons. Our town benefits greatly from on

If you’re a child of the 1960s or before, you may recall the first oil embargo when prices spiked and shortages had drivers wasting weekends in line at the gas pump, like we saw in May 2021 on the E

If music is how we feel math, then sailing is how we live physics. And sail trim, like playing an instrument, is our touchpoint with the medium. In fact, apart from steering a sailboat, which is one o

Sailing can seem bicameral—like a 50/50 Senate—split between racers whose passion is intense competition, strategy and speed, and cruisers seeking fun-in-the-sun and vacations to exotic locales.

Before Covid-19, sailing seemed stuck in place: it was the same boats moored in the same marina sailing to the same destination or starting on the same line and racing the same course against the sa

The question I’m asked about most often is about family sailing. The scenario differs only slightly: Usually a parent of teenagers aspires to sail in a family group, but can’t convince the kids to

Memories of post-race parties run together, but one stands out, not just for the fun being had (fun was definitely had) but for the shocking dockside news that awaited the unknowing fleet. After thre

Sailing boasts unmatched power to make quick comrades from nemeses. For example, when climate change provocateur Greta Thunberg chose to sail across the Atlantic Ocean instead of flying, sailing soci

It was a quarter of a century ago but it seems like yesterday. We were 50 miles into a 120-mile overnight passage bound north by northeast. Our homeport lights had fallen below the horizon  so o