Certain boatyards always seem to attract would-be voyagers with large ideas, small budgets and vessels of suspect provenance. I once kept a boat in one such yard in midcoast Maine, at the back of which was a handful of bizarre project boats. Most of these never came to anything and sat idle on their jackstands year after year. Occasionally their owners appeared, worked on them for a day or two, then disappeared again like vampires dissolved in daylight.

There was one man—I’ll call him Harold—who was different from the others. His boat was a crude slab-sided dory with an ungainly cabinhouse slapped on top. Harold had designed this vessel himself, pretty much making it up as he built it. It was constructed mostly of plywood and cheap pine two-by-fours. But what was different about Harold was that he actually worked on his boat. Not maniacally, but steadily, like a marathon runner with his eye on a distant finish line.

Harold’s ambition was very modest. Once he completed his boat he wanted to sail it down to Portland and live on it in a marina with his girlfriend. Once they saved up some money, he then hoped to cruise down the coast to Louisiana, where he’d been born and raised.

I often walked over to visit Harold and follow his progress. One big milestone, I remember, was when he poured his keel. He built the mold himself, gathered a huge collection of stray bits of lead—old fishing sinkers, diving weights and what-not—melted it all with a blowtorch, and thus fabricated some ballast. Soon afterward he stepped his mast, a spindly tree limb with the bark stripped off. I noticed it leaned to port and was supported by three skinny wires.

“What sort of rig will she have?” I asked, hoping to inject some reality into the proceedings.

“It’ll be a gaff rig,” explained Harold with some gravitas. “I think a low-stress, low-aspect sailplan will work best on a boat like this.”

In November I visited again and was amazed to find the boat was nearly finished. She was all painted, rudder in place next to an outboard engine on a stern bracket, stanchions and lifelines installed, her crooked rig poking skyward and her equally crooked keel pointing down. Down below, Harold and his girlfriend were hard at work finishing the crude interior.

“We’ll be up until midnight,” he conceded. “But tomorrow we’re off to Portland. I’ve reserved a berth for the winter.”

I lost sleep that night worrying over Harold’s fate. Though he proposed to sail his boat only some 60 miles, all within sight of land, I felt this must be, as the Coast Guard would put it, a manifestly unsafe voyage. I wondered if he shouldn’t be stopped, but I also admired him for following his dream so intently.

A few days later I returned to the yard and was relieved to see Harold’s boat in its familiar spot. “He never launched?” I asked Scott, the yard manager.

“Oh, he launched alright,” answered Scott and shook his head sadly.

It was not a pretty tale. According to Scott, the boat started leaking badly the moment it was clear of the Travelift. Then, as Harold tried to maneuver back to the lift, the thrust of the outboard wrenched its bracket off the transom. Finally, in the midst of all this, Harold’s truck, which he left parked at the top of the low hill leading down to the slipway, slipped out of gear and rolled down the hill into the water.

So Harold’s dream lay fallow for another winter. In the late spring, however, when I returned to the yard, I saw his boat was already gone. That summer I spied her from a distance in a marina berth in South Portland. By the time fall arrived she had disappeared.

I often wonder if Harold ever made it to Louisiana. I like to think he did, though I am sure he suffered many mishaps along the way. Of such stuff is adventure made. It is easy enough to make your dreams come true if you have resources and expertise, but the most beautiful dreamers are those who sail on a wing and a prayer.

SAIL’s Cruising Editor, Charles J. Doane, sails his Tanton 39 on the Maine coast and down in the West Indies whenever he gets the chance. He is the author of The Modern Cruising Sailboat, published by International Marine, and is a contributing blogger at SAILfeed.com

September 2016