I was introduced to the Bristol Bay gillnetter Admirable in the long, lingering twilight of a balmy midsummer evening in 2008. I’d like to report that it was the beginning of a beautiful friendship, but my encounters with the Admirable have been more complicated than that, by turns challenging, frustrating, rewarding and even embarrassing—kinda like some human relationships I’ve had.

The Admirable is part of the fleet of historic vessels at the Center for Wooden Boats in Seattle. After volunteering for several years at the center as a dockhand, assisting with rentals of Blanchard Jr. Knockabouts, Beetle Cats and other small daysailers—mostly to earn free sailing time in the boats for myself—I got an email from the center asking if anyone was interested in learning to skipper the Admirable. She could then provide free rides to the public at the upcoming Wooden Boat Festival over July 4th weekend, and on Sundays year-round.

That sounded like fun to me. I knew nothing about the boat but I liked the idea of earning sailing time by actually sailing, instead of by tending dock lines for other sailors. Plus, I thought “Capt. Greg” had a nice ring to it.

Eric, the center’s young, blond, always barefoot rental manager, met me at the dock to teach me the Admirable’s ways. Any notion that she would be like the easy-to-sail pleasure craft in the center’s rental fleet was quickly dispelled when Eric showed me how to rig the boat.

To begin with, the Admirable is a working boat. A 32-foot double-ended open catboat built around 80 years ago with oak frames, cedar planks and fir decks, it was based on a design that originated in San Francisco in the 1860s. The earliest boats were used for gillnetting salmon in the Sacramento River. When those stocks were depleted, fishermen took the boats north to the Columbia River and eventually to Bristol Bay in Alaska.

Until 1952, motors were not allowed in the salmon fishery on Bristol Bay. Depending what source you consult, that measure was intended either to protect the salmon population or as means for the canneries, which owned the boats, to suppress economic independence on the part of the fisherman. In any case, that helped preserve the wooden boats used there. The Admirable bears the A.P.A. marking of the Alaska Packing Association and the lettering NN for Naknek, a fishing village on Bristol Bay.

Each boat carried a crew of two men, who would fish until the boat was full—with up to 10 tons of salmon—and then head in to unload their catch. The men brought a cook stove aboard to prepare meals and often pitched a tent on the tiny foredeck to sleep in. The work was hard and dangerous, with strong winds and currents, shoals and mud flats to contend with, and not every fisherman made it back.

Gill nets hang in the water like a curtain, suspended from floats at the surface and stretched down by weights at the bottom. Once the net was played out, the boat would simply drift with it. Encountering the net, salmon would try to swim through it, but could get only partway through because of the mesh; when they tried to back out, the net would snare them by the gills, until the fisherman hauled in their net and dumped their catch in the boat.

Back to Eric and me on the dock. Most boats I’ve sailed carry a triangular mainsail stretched between the mast and a boom that is permanently attached to the mast near the deck. But not the Admirable. Its big, four-sided main is spread from a short, unstayed mast by a boom and also by a sprit, a second spar that angles up to the peak of the sail above and aft of the mast top.

Neither the boom nor the sprit is permanently fixed to the mast. Instead, each is held in place at its mast end by something called a snotter: a line-and-block contraption that clips onto a metal staple on the mast and is threaded through a groove in the end of the spar, and then cleated off to hang from the mast. The other end of each spar is attached to the sail: the boom, by a simple rope loop at the lower back end (clew) of the main; the sprit, by a line from the peak that is run through a pulley at the end of the sprit to extend the sail.

Needless to say, rigging the Admirable is no simple task, and it takes two people to do it. As to why the boat carries such a strange rig, the best explanation I can come up with is that the setup allowed the fishermen to strike the entire rig quickly (as is done when the boat docks at the center). At sea, while drifting with the net or hauling in the catch, the fishermen could lash the boom and sprit to the mast and bag the sail, leaving them free to work on deck without worrying about all that stuff getting in the way.

Once rigged, the Admirable doesn’t exactly sail like an America’s Cup contender: She’s a garbage truck to the Miatas and Mini Coopers of the daysailers. Like most catboats, carrying a single sail on a mast set well forward, she doesn’t point upwind very well. She wants, to, though, and if you’re not careful, she’ll ease into the wind from a close reach and stall—not a sail-flapping, dead-into-the-wind stall, but a stall nonetheless. Nor does she tack readily, especially with a full load of passengers forward, where the seats are. And here’s the beauty part: She doesn’t like to fall off the wind, either. Fortunately, she’s equipped with oars and oarlocks.

My initial sail aboard the Admirable went fine. In a light to moderate breeze, with only two of us on board, she handled OK, if not exactly nimbly. With the wind from the south, docking her was pretty easy. And most of my subsequent voyages, skippering the Admirable on hour-long public sails on Lake Union, have been similarly uneventful.

But not all.

With the need to focus so much on properly rigging the boat, it’s easy to overlook some other pre-departure considerations—like making sure the removable tiller has been reinserted in the rudder before leaving the dock. I forgot that one once; fortunately, though, I had asked a dockhand to hold onto the stern line until the boat picked up the southerly breeze and sailed away.

So it didn’t seem like a big deal to stick the tiller in its hole—although a piece of wood had somehow gotten stuck in there and had to be pried out with the knife of another dockhand—and sail off, even if the bow had swung to the east and was pointing across the narrow channel to the fancy yachts docked on the other side. It was simply a matter of turning the tiller, now properly in place, to sail to the north, downwind.

Except that the Admirable didn’t want to sail downwind. With the centerboard down—something else I overlooked—she stubbornly tried to pivot around it and head upwind: tiller, schmiller. My volunteer crewman was not quite agile enough to scramble onto the foredeck and fend us off. Fortunately, the damage was slight: Our boom scraped lightly along a yacht’s hull, and there was a bit of crinkling of a metal vent hood. Nothing too serious, though I did have to fill out an incident report at the center.

Then there was the bright, sunny Sunday with a spanking breeze from the north. I looked forward to this sail because there are times, on a beam reach in a stiff breeze, when the Admirable cracks along with satisfying alacrity. Any problem with leaving the marina was resolved when one of the center’s powerboats towed us well clear of the docks.

But sailing on the open lake was another matter. Twice the boat got stuck in irons in the middle of a tack. On one of those occasions she got blown backward, toward a line of yachts docked by the shore. No doubt the passengers were deeply reassured to see Capt. Greg clambering onto the stern to fend off with his feet. The judicious application of an oar on one side of the boat served to get us back on course.

Then there was the matter of returning to the marina. The Admirable drives downwind at a good clip under that big main, which is controlled by a long sheet that runs through a pulley hung off the boom, with one end permanently wrapped around a thole pin and the other held in the hand. Streaming dead downwind toward the center’s docks, I thought it would be a good idea to take some of the power out of the sail before attempting a U-turn in tight quarters to dock her.

With my right hand on the tiller and my left holding the sheet, I attempted to sheet in the main. But I lost my grip—and in another of those pesky oversights, I had neglected to make sure to tie a stop knot in the end of the sheet. The line ran through my hand and the block, and the main, with nothing to restrain it, swung forward all the way until it was pointing straight ahead over the bow, creating a horrendous snarl of lines and blocks and spars and snotters in the process.

As my former newsroom colleagues can attest, I’ve been known to nut out over relatively minor irritants in the office. But for some reason, on the water I’m the picture of aplomb in the face of adversity. While acutely aware that the Admirable struck an embarrassing profile, I simply steered the boat in a hairpin turn—if nothing else, I had succeeded in drastically reducing the force on the sail—and pointed her upwind. With a little help from dockhands fending her off, I brought the Admirable alongside as she stalled into the wind.

With a hand from a volunteer, I untangled the rig, took it down and set it back up again it record time, ready for another skipper to take her out. And maybe I’d like more scrambled egg on the bill of my cap and less on my face, but we didn’t hit anything and nobody was hurt—which adds up to success in my book. As for those smirking sailors in their simple Marconi-rigged sloops, all I say is, well, look out!

Gregory Roberts is a sailor and freelance writer based in Seattle.