2025 March 14
As often happens for my musings in this column, three things converged like a perfect storm to make me start thinking. First, being a car nut as well as a boataholic, I visited a friend who is in the
Home / Columns & Blogs / On the Wind
2025 January 1
The future of the sport of sailing might depend on the hierarchy on your boat.
From something akin to a dictatorship to something much closer to a democracy, there are four ways that crews tend
2024 November 1
This being the New Boat issue, and since I’ve owned more new boats than the U.S. Navy, I have (he said modestly) a wealth of wisdom to share.
I’m here to offer the Caswellian Boat Survey Tips, wh
2024 October 1
No one is more passionate about their version of sailing than a multihull sailor. It is as if they know something that the rest of us are missing. One avid friend has introduced hundreds of guests to
2024 September 1
It was a Christmas morning decades ago, and I leapt down the stairs to see what was under the tree. But it wasn’t the usual mishmash of large and small packages, bearing the mix of new shirts, belts
2024 July 1
If you consider the rising costs and barriers to insuring a sailboat, you might think the actuaries see dangers that we sailors can’t see.
But is there any reason to be concerned? One state
2024 June 1
Years ago, I was very much into landsailing as well as sailboat racing. Born and raised in California, I was surrounded by dry lakes so hard you could rollerskate on them (people did). On a weekend, y
2024 April 1
Escapism is built into the human psyche, has genetic and evolutionary roots, and persists in story across the millennia. So the trend to sell everything and sail isn’t new, despite the mob of tan, n
2024 March 1
My dad was an executive for Douglas Aircraft and we lived in Tucson, Arizona, when I was a kid. As a young man, my father had run away to sea, shipping out on tankers and working his way up to navigat
2024 January 1
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?”
2023 November 1
My dad was an executive for Douglas Aircraft and we lived in Tucson, Arizona, when I was a kid. As a young man, my father had run away to sea, shipping out on tankers and working his way up to navigat
2023 October 1
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
2023 September 1
OK, I promised you no more America’s Cup rants but, hey, you know you can’t trust me. The Cup is a sad, broken, shadow of an event that once enthralled sailors worldwide. How many of us sat up int
2023 July 1
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
2023 June 1
In the process of learning to sail, there is one thing that is not often taught yet it is extremely important. It falls somewhere between learning to duck your head on a jibe (ouch) and not getting yo
2023 April 1
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
2023 March 1
In World War II, aviators had what they called the “Caterpillar Club.” It was an organization for pilots and aircrews who had “hit the silk” by parachuting out of their damaged aircraft. I’m
2023 January 1
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
2022 November 1
Disclosure: I love sports cars. I’ve loved them since I didn’t have a driver’s license and, since then, I’ve owned them, restored them, raced them and often sworn at them. It’s exactly like
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A handsome cruiser has plenty of options
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This midsize cruiser has plenty of elbow room
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This cruiser has plenty of options for comfortable family cruising
