On the Wind

2025 March 14 - 12:00 am

Bargain boats found in old barns should star in fixer-upper shows

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

On the Wind

2025 March 1 - 12:00 am

It floats! Thanks to a degree from the North Lawn School of Design

By Chris Caswell

On the Wind

2024 November 1 - 12:00 am

Caswellian rules for boat buying success

By Chris Caswell

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

Features

2024 September 1 - 12:00 am

Sailing's Forgotten Coast

Easy to get to and full of beaches, birds and bountiful in character, the thin water cruising in southwest Florida is not to be missed

By Chris Caswell

We’re all hoping to find charter areas that are overlooked, if only to get away from crowded anchorages, crowded restaurants, crowded pubs and, frankly, the crowds themselves.Picnic Island is perfec

On the Wind

2024 September 1 - 12:00 am

A charter cruise is a gift that keeps on giving

By Chris Caswell

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

On the Wind

2024 June 1 - 12:00 am

Get off the foils and bring back sailing before it’s lost forever

By Chris Caswell

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

On the Wind

2024 March 1 - 12:00 am

Fitting out is best when you follow the 10 Caswellian Laws

By Chris Caswell

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

On the Wind

2023 November 1 - 12:00 am

Sailors’ reputations are built at sea not by who they are on land

By Chris Caswell

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

On the Wind

2023 September 1 - 12:00 am

America’s Cup crew may not be sailors, at least they are human beings

By Chris Caswell

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

On the Wind

2023 June 1 - 12:00 am

Sometimes the most important learn-to-sail lesson is to play nice

By Chris Caswell

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

On the Wind

2023 March 1 - 12:00 am

Practice makes perfect when an idiot with his pants down goes overboard

By Chris Caswell

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

On the Wind

2022 November 1 - 12:00 am

The America’s Cup has moved so far from the glory days it might as well be on the moon

By Chris Caswell

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

On the Wind

2022 June 1 - 12:00 am

Don’t waste good champagne to christen a boat with a dreadful name

By Chris Caswell

It was a beautiful morning and I was rowing our tender ashore to grab a Sunday paper. I like rowing, and the fiberglass tender is fun for rowing (unlike those baggy gray inflatables), and I didn’t w

On the Wind

2022 March 1 - 12:00 am

Fitting out projects require an educated thumb, just don’t varnish naked

By Chris Caswell

When it comes to refitting your boat, whether it’s for the upcoming season or to upgrade it in general, I’m happy to report (from more boats than I’ll admit to), that there is one item that does

On the Wind

2021 November 1 - 12:00 am

Slippery bottoms are the key to go-fast sailing

By Chris Caswell

We were standing in the yacht club bar after the race when Jon arrived and grabbed my arm. “Were you just feeling her bottom?” he demanded, which turned every ear along the bar into little pointed

On the Wind

2021 September 1 - 12:00 am

Trust what your eyes tell you, and you will always know how the wind is blowing

By Chris Caswell

I was considering the 55th anniversary of SAILING, and I asked the question, “What is the one thing that binds all SAILING readers together aside, of course, from great photos and even greater

On the Wind

2021 June 1 - 12:00 am

Sailing affirmations can unlock your best self

By Chris Caswell

She Who Must Be Obeyed is a big believer in affirmations. Until she entered my life one spring vacation many moons ago, I freely admit that I didn’t know what an affirmation was. Or, at least, I did

Boat Test

2021 May 28 - 12:00 am

Leopard 42

This new cruising cat has all the luxury features and speed performance of its bigger sisters in a compact, easy-to-handle package

By Chris Caswell

Full disclosure: I love Leopard Catamarans. I’ve “owned” several, admittedly only for a week at a time on bareboat charters, but that was enough to find them fun to sail, easy to maintain and ve

On the Wind

2021 March 1 - 12:00 am

When America’s Cup sailors suit up for battle, they ditch the Topsiders and khaki shorts

By Chris Caswell

Last weekend, with a fine breeze blowing, I decided to take the Laser out. Me to She Who Must Be Obeyed: “Hey, honey, do you know where my oxygen tank and mouthpiece are?” SWMBO to me: “Where t

On the Wind

2020 November 1 - 12:00 am

The luxury of onboard showers can leave you all wet

By Chris Caswell

Full disclosure. I love showers. Hot showers. Long, hot showers. I have done some of my best thinking during a leisurely shower, and it reached the point where I installed my own waterproof notepad: a

Easy to get to and full of beaches, birds and bountiful in character, the thin water cruising in southwest Florida is not to be missed

This new cruising cat has all the luxury features and speed performance of its bigger sisters in a compact, easy-to-handle package

Perry on Design

A handsome cruiser has plenty of options

This midsize cruiser has plenty of elbow room

This cruiser has plenty of options for comfortable family cruising

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