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My Sailboat Dalliance

Not having a boat can drive some people a little crazy. Here’s what it did to me.

Boatlessness does strange things to a boater’s psyche. At least that’s my experience. And to further explicate the phenomenon, please allow me to describe the bizarre state of mind I fell into during the long, glum, boatless period that stretched between the sale of my Grand Banks trawler a year or so ago and the recent purchase of my new (to me, that is) Cape Dory 28 Flybridge Cruiser. 

Did I say boatless? Well, let’s get real! The period to which I refer did indeed start out boatless, but then it evolved, rather sportily, into a super-savvy sort of situation that promised both radical cost-cutting and increased boat usage and convenience, all in one fell swoop.

“I’m thinking about buying a trailerable sailboat—whataya think?” I asked my lunch buddy, Don, right before hitting him with all the plan’s benefits, which included slashing the base price, nixing slip fees, cutting insurance premiums, guaranteeing at-home access for DIY projects, and lots of spur-of-the-moment cruising.

Don gave me one of those baleful looks that reasonable people use on the insane. “It’ll never leave your driveway,” he said, “And even if it does, you’re not going to have enough time to sail it.”

The comeback came easy. Heck, I’d once lived on a sailboat, a 29-footer—decades before, when I’d worked on oceangoing tugs. Why shouldn’t a nice guy like me return (or semi-return) to those carefree, bygone days, when work was one-month-on, two-weeks-off, the wind was free, the living easy, and shorts, deck shoes, and T-shirts constituted my entire wardrobe?

Trouble started soon after the purchase. First up: the carport issue. Would my wife allow my new trailer sailer to displace her BMW, except for varnishing purposes? Nope. Second, I had to soon admit that the actual rigging of the boat, both prior to trailering and to launching, was way more laborious than I’d imagined, due to a devilishly difficult array of cotter rings and other paraphernalia that had to be dealt with. And third, my ability to sail a small boat under duress, I also had to admit, had faded somewhat with the passage of time.

My trailer sailer’s final sail brought things into perspective. It started late on a Sunday, due to a commitment I’ve had for years on Sunday mornings. By the time I got my boat hauled to the lake, the mast stepped, the sails hanked on, and the outboard hung, it was pushing 3 o’clock in the afternoon, which put me under so much time pressure that I pulled an amateurish stunt. I forgot to insert the drain plug!

“Hey bud,” yelled a fisherman from under a straw hat after I’d parked my vehicle and trailer après launch—he sat on an overturned 5-gallon bucket near the boat-ramp dock, “Yer boat’s sinkin’.”

This news precipitated one of the fastest boat-ramp retrievals ever to grace the great state of Florida. But by the time I was ready for the second launch, it was really late, and I wondered, “Do I really have time to sail this puppy? Cripes, it’s 5 o’clock and I still gotta de-rig and drive home afterward.”

What the heck, right? Despite the hour (and with the plug secured), I relaunched and motored out into the boggy lake, where the lack of shade soon became an issue, as did the sweaty lack of wind. 

About 7 o’clock, though, dark clouds gathered, signaling a squall. And as the squall came closer, the wind picked up, the air cooled, and everything got groovy, although I do remember telling myself, to no avail, while scooting joyfully along: “You know, for safety’s sake, you really should put a reef in that mainsail.” 

When the squall hit, so did mayhem. How I kept my trailer sailer from capsizing while wildly tacking back and forth in 30-knot zephyrs is beyond me—adrenaline can trump talent, apparently. And to say that I was frazzled, bedraggled, and adrenaline-crazed by the time I got home that night would be an understatement.

You were right, Don. A trailer sailer? Really? I sold her to a retired guy with plenty of free time, and bought the Cape Dory—a gorgeous, ready-to-roll-at-the-drop-of-a-chapeau, diesel-fueled powerboat!