If there’d been any chance of avoiding the whole extravaganza, I most certainly would have. I was dog-tired, having been underway since daylight, wheeling the Betty Jane down an increasingly lumpy Chesapeake Bay. It was pitifuly late, although a good-hearted guy at Somers Cove Marina had promised me on the VHF that he’d stick around past closing time. It was dark, with rain sluicing down in buckets and the wind whooping straight out of the north at dang near 25 knots. And it was also cold—so freakin’ cold that I had to literally force myself to leave the warmth of the lower helm station for the wind-whipped flying bridge, where the visibility was better for close-quarters navigation. The comfort level was on par with taking a cold shower with your clothes on.

I squinted anxiously ahead. My first order of business as I eased Betty‘s nose into Somers was to find the fuel dock and tie up there; our two tanks were gettin’ low, and I wanted ’em topped off so we’d be ready to boogie early the next morning. Then, gloomily enough, the next order of business was to somehow safely shepherd the boat into a slip for the night, hopefully stern-first, since my shore-power connection is at the rear of the cockpit. “There’s our guy wavin’ from over there,” yelled my copilot and traveling buddy Chuck, who wore an old military poncho against the rain and looked like a storm-tossed tent on the verge of blowing away.

Chuck was right. The guy was just off to starboard, maybe 100 yards, beaming a flashlight back and forth across a diesel pump emblazoned with a familiar logo. I aimed for him and began sizing up the situation. The wind was coming at us, almost directly off the fuel dock. What we needed to do, the way I had it figured, was to get in close and alongside, rifle a line to the guy from our port spring cleat, have him expeditiously absorb all possible slack and make fast, and then use the oomph of our Super Lehman diesel to spring Betty into the dock so Chuck and the guy could get a few more lines on.

All went well. Chuck got the springline across successfully, the guy understood the plan almost instantly despite the difficulty of shouting over the wind, and Betty slowly (and I mean slowly) overcame Mother Nature’s power, finally sidling close enough to the dock for bow and stern lines to be properly dealt with.

“The name’s Al,” yelled the guy, starting to drag a fuel hose. Then, he added, as if to explain why he had agreed to play good samaritan and stay beyond working hours to pump fuel and help tie up, “Just couldn’t leave anybody stranded on a wicked night like this.”

I was concerned about getting rain water down the fuel fills, so I hunkered over each to shield it with my slicker-suit-clad torso while fuel gurgled into each tank. Because the pump was slow, I had plenty of time to think about the second order of business I just mentioned, parking Betty stern-first in the only empty slip.

Talk about a hairy deal! The slip was 50 yards distant, across a narrow fairway, and its axis was virtually parallel to the face of the fuel dock. Which meant, of course, that the wind was whipping straight across the line of travel I’d have to approximate if I was ever going to back in. Yikes!

A committee convened between my ears, the same dreary bunch that always gets together to comment and advise when things start lookin’ bleak. Each and every one of the little devils was perfectly aware that, having only recently become the proud owner of a small, thrusterless single-engine trawler, I had virtually no experience with backing such a vessel across the wind into a slip on a rip-snortin’ night. And each and every one was antsy to toss in his two-cents’ worth.

“Bill, you’re a goner,” howled the loudest of the lot. “This deal you’re fixin’ to get yourself into over there would challenge a guy who knows what he’s doin’! For a goofball like you who’s barely got a clue? We’re talkin’ horror show, baby. Horror show!”

“Sad but true, my friend,” chimed in the other serious loudmouth, an intellectual-sounding dude with a penchant for doom and finality. “And Bill, just imagine the carnage once the wind really takes hold. Think about how you’ll feel once you take out the bowsprits of three or four sailboats and your beloved Betty Jane starts sinking slowly right in front of the dockmaster’s office. And by the way, Bill, are your dues paid up on the ol’ insurance policy?”

This went on and on. And it rattled me some, I gotta admit. But then, as luck would have it, a plan began to form. It was a simple, hopeful one that arose almost unbidden from a place far beyond the machinations of my dour cerebral cortex. An admonishment from Chuck started the ball rolling. “Bill,” he said at an especially grim juncture where the committee was double-teaming me big-time. “You’re thinkin’ too damn much! Relax, man!”

Whew! The dread tussle went off slicker than a wet porpoise. After tossing off our lines so the wind could separate us from the dock, I simply backed Betty up the fairway, straight into the eye of the wind, until she was well above the slip. Then I kicked her stern slightly sideways to approximate a diagonal drift back down while simultaneously easing astern. Yeah, I had to make a slight orientational adjustment toward the end so I could slide into the opening of the slip, but otherwise the whole shebang was accomplished with considerable ease and precious little cogitation.

“Nice job,” said Al once we’d finished tying up.

“No brainer,” I replied, slapping Chuck on the back.

Hear Bill Pike narrate this story in a podcast.

This article originally appeared in the June 2008 issue of Power & Motoryacht magazine.