OK, I admit it. I’ve been a harsh critic of helicopter parents for a long time. You know, the parents that hover around their children, never giving them a chance to think or do on their own. They rig their boats, follow them on the racecourse aboard mommy boats, hire coaches to video and critique them.

They’ve created a generation that expects everything to be handed to them, and who can’t find their own fun away from a video game and are unable to make decisions. Spoiled namby-pambys who have been cossetted and coddled and celebrated for every non-achievement. 

We’ve had the Baby Boomers, Gen-Xers, Millennials, and now we have the It’s-All-About-Me generation.

But I’ve been seeing what I consider to be another troubling trend and, in a surprising move for Caswell, I think it’s time for kids to start hovering about their parents who are about to do something stupid.

Let me explain. In the past few months, I’ve been present on several sea trials for largish yachts in the 60-foot range. Not a big deal, because I do a whole lot of sailing every year. But these were indicative of a trend that I’ve been seeing more and more: people packing it in, selling everything and going cruising. 

Wait a minute, you say. Haven’t you been promoting the sailing lifestyle all your life? Isn’t this the rainbow at the end of a lifetime of slaving away in office cubicles? Doesn’t everyone tack a postcard on their bulletin board showing an orange sun setting over an anchorage in the South Pacific, with jagged mountains and a palm-fringed beach?

Yes, indeed. But what I’m seeing is the adult version of those coddled kids heading out into the world totally unprepared. These are adults doing the same fool thing. And I find it disturbing.

Case in point: Brand-new 65-footer that’s very nicely equipped,  with a generator, air conditioning, freezer for weeks of food, dive compressor and an array of electronics including an autopilot that links to the wind indicator to steer by the wind. The electronics package alone was somewhere on the north side of $100,000.

A nice couple, they’d had a 37-footer and had long dreamed of their Big Adventure, which would include ocean crossings to various Caribbean islands, cruising the Central American coast and then off across the Pacific. 

Had they ever completed an ocean passage of even two nights at sea? Nope and not concerned.

Did they know celestial navigation? Nope and not concerned because first, they had $100,000 worth of electronics and, second, he’d bought a plastic sextant and was planning to teach himself celestial while cruising. To me, with my innate distrust of putting my life in the hands of a black box, that is like jumping off a cliff and sewing your parachute on the way down.

In view of their impending, long nonstop passage up the East Coast, I asked what they planned for a watch system? Six and six? Four and four? I was met with blank looks and a mumbled “I guess we’ll just sleep when we can” response.

So here they are with the shiny keys to their new toy and, as far as I can see, totally clueless about getting a powerful yacht from Point A to Point B.

Case No. 2: Again, a nicely equipped 61-footer and a plan to sail across to the Mediterranean. And, yes, a level of experience that would make a one-day coastal cruise pretty iffy. To add to this, the builder had put everything on the mast, which meant that, when it’s blowing dogs off their chains, someone must go forward to reef the main or douse the jib. And that, folks, is just plain scary. Not a big problem (except for wind and seas) on a sunny afternoon. But having to reef the main when you’re offshore only happens at zero-dark-thirty in the wee hours, with no moon and the bow tossing solid green water aft. 

A few years ago, I had a neighbor in a nearby slip with a pleasant cruising boat and he fit into this cruising mold—empty nester and retired. But he spent a lot of time getting his boat right, with electronics backed up by paper charts and seamanlike rigging. Even more importantly, he then worked on getting himself right (he would be a singlehander). He learned celestial while still on land, and he made several, long nonstop passages up and down the coast in all sorts of weather to, as he said, “suss it out.”

And then he got cancer and was going to sell the boat. I argued with him, told him to go, that he was ready and why not? He did, and his postcards remain my prized possessions, tales of calms and gales, parts he needed me to send and things he’d learned. And, yes, there was one with an orange sunset over a bay on Moorea with a flawless beach and palm trees. In the end, the Big C caught up with him in Thailand, but he’d had a wonderful two years because of his preparations.

The headlines have been increasingly filled with stories about well-found cruising yachts abandoned offshore because it wasn’t what the crew aboard were expecting. It was rougher and tougher than those pretty postcards. The yachts were still afloat and, in some cases, the rescuers had to sink the yacht to keep it from being a danger to others. It was the people that had failed.

So for all you kids out there whose parents mollycoddled you and spoiled you and fussed over you, it’s time to pay it back. You may have left home which encouraged your empty-nester parents to sell everything. You may be married with kids, you may have a successful career. 

But you need to sit down with your parents and protect them from themselves. You need them to earn some experience with offshore sailing before they cast off on The Great Adventure. Encourage them to keep The Big Dream but just start thinking rationally. Even sending them, just the two of them, on a bareboat charter in the British Virgins all by themselves might open their eyes. 

I don’t want to discourage anyone: I just want them to be prepared. The Coast Guard already has its hands full without adding your parents to the list.