Cal 25 – The Original Sport Boat

Long before anyone slapped the words “sport boat” on a sailboat brochure, there was a stubby little 25-footer out of Costa Mesa, California, that beat everybody to the punch. The Cal 25 wasn’t marketed as revolutionary. It didn’t have a marketing department dreaming up a category for it. It just showed up in 1965, went … Read more

Insurance Companies Are Killing Old Boats (One Survey at a Time)

If you own an older boat — and if you’re reading this, there’s a decent chance you do — you’ve probably noticed the same thing I have: getting insured is getting harder, not because your boat got worse, but because the actuarial tables got stricter. Somewhere in a windowless office, a spreadsheet decided that fiberglass … Read more

7 Things I Wish Someone Told Me About Sailing From Day One

Nobody hands you a manual for this. You get a boat, a vague sense of confidence borrowed from a weekend course, and a whole ocean’s worth of ways to be humbled. The good news is that every mistake you’re about to make has already been made by somebody else — usually several thousand somebody elses, … Read more

10 Boating Laws You’re Breaking (Without Realizing It)

You feel free out there—wind in the rigging, horizon wide open—but the law is quietly on board, too. Coast Guards don’t accept “I didn’t know,” insurance won’t cover “Oops,” and that sleepy cove you anchored in might be off-limits. Here are the 10 rules sailors break most—and how to avoid getting boarded, fined, or denied … Read more

So You’ve Been Invited Sailing: Boat Guests Do’s and Don’ts.

Somebody invited you sailing. Congratulations, and also, condolences, because you are about to learn that “a nice relaxing day on the water” is one of the great lies of modern hospitality. It can absolutely be relaxing. It can also turn into a floating classroom where you are graded in real time on whether you understand … Read more

10 Sailboat Brands with Horrible Reputations

There’s a special kind of silence that falls over a group of old salts when somebody pulls into the anchorage on one of *these* boats. You know the silence. It’s not rude. It’s the silence of people choosing their words carefully. The silence of a man who once did a survey on one of those … Read more