An Afternoon Sail with Gentleman of Australia


CAIRNS, AUSTRALIA- “Be at the Salt House at noon with a case of peach cider.”

My instructions for Wednesday afternoon were crystal-clear, and I was reasonably confident I could execute them without too much trouble. It was my first time as a guest crew member for the Cairns Yacht Club’s WAGS, or Wednesday Afternoon Gentleman’s Sail. In a small twist of irony, I was the guest of Ashley, a friend of a friend I met while doing some late-night fishing off of the docks the week before. Ashley was a young American like myself, fed up with the rigors of the middle-class professional lifestyle in which she found herself mucking about, life myself, inspired to approach her life in a new and different way by Tim Ferriss, like myself, and had spent the past six months learning to sail under the tutelage of Kip, an Aussie captain with whom she struck up a strong rapport, most decidedly unlike myself.


I was intrigued as to how Ashley got into sailing, though it was really quite a simple story. Enamored with the idea, she enquired at the Cairns Yacht Club regarding opportunities for someone like herself—young, open minded, and willing to work. I’m sure it didn’t hurt that she’s a pretty young blonde, but nonetheless she was told about the Wednesday Afternoon Gentleman’s Sail.


WAGS is a casual sailing event where all the ole’ boys from the yacht club skipper a boat in a casual afternoon race around the inlet just outside the marina. The only catch is that WAGS starts at 1pm, sharp. Most of the older members can make it—their schedules are flexible and they can sail in the middle of the week, but enough don’t show that they are always in need of extra crew. Ashley had been a member of Kip’s crew for 6 months or so, and I was the newest addition. My knowledge of sailing extends to the awareness of words such as ballast, port, tack, starboard, sail and race. Beyond that, I didn’t know jack about racing a sailboat, but was told as long as I have four functional limbs it wouldn’t be a problem.


Arriving at the Salt House, I noted that this truly was a gentleman’s afternoon. Lunch began with a round of Old Fashioneds, and much as would have liked to indulge myself, I had just purchased a $22, 12-pack ticket for the afternoon and my backpacker’s budget was loathe to indulge in a fanciful, albeit worthwhile, treat that would impair my senses. I could, however, shoot the shit with the guys, and started learning everyone’s name, especially Kip’s. It's poor form to forget who your captain is.


Setting off towards the docks, I fell into stride with Kip. Kip is a tall, ruddy-faced Aussie with a personality that is best described as a presence that is felt. Tall and deliberate in motion, that day we shared one thing in common: the fact that we were both wearing red shorts.


“Well”, I remarked, “I didn’t realize that it was a requirement that captains wear red shorts.” He paused for a beat, confused, and then burst into laughter when he realized that I was simply taking the piss. Aussies prize the ability to be a cheeky bastard, and Kip was no exception. I hoped that I endeared myself to him. It was his ship, after all.


It was a beautiful day for a sail, which was fortunate—the spring weather in Cairns is known to be finicky. At the end of the rainy season precipitation was rarely in the forecast, but always a possibility. Clouds linger ominously around the mountaintops and always threatened a perfectly lovely day with the possibility of a downpour. The wind could bite, especially when you’re out on the water, and force you into a long-sleeved shirt against your best and brightest wishes. Yet that day, there were none of those things. The sky was as blue as could be and the water was a crystal azure, inviting you to come play. The wind could be appropriately described as a “refreshing breeze”, but was not enough to be chilly. The sun was predictably strong; strong enough for me to need sunscreen. I needed it almost every day, living in Cairns.


Walking up the dock towards the boat, soaking up the beautiful day and the prospect of learning something completely new in one of my favorite places in the world, I found out that it was not, after all, Kip’s boat. The vessels themselves belong to the Yacht Club, or some benefactor of the Yacht Club, and Kip was simply the skipper. Not that it made a material difference to me, but my perception was that I felt more comfortable being on a boat without the owner present. In a sense, we’re all guests. After helping to load the boat with the various accoutrements for the afternoon—a few cases of cider, some sailing gloves, and copious amounts of sunscreen, we were ready to board and introduce ourselves.


Surveying the crew, it was apparent that Claude was the first mate. Claude was the opposite of Kip: short and stocky with muscular, with sculpted 65-year-old biceps and a relaxed, easy-going demeanor. He’s retired, and relishes the opportunity to sail because of the freedom it awards him: an afternoon away from the wife, away from the worries of his casual, retired existence; an afternoon where all he has to do is tell the schlub working next to him when to pull the ropes like hell to tack the boat. Today, I have the pleasure of being that schlub.


Once we’re on board it’s immediately apparent that Kip is in charge, and that Kip sails to win. More specifically, Kip sails to beat Dex Fielder. Dex Fielder, from what I gather, is an evil, slithery bastard who feasts on dingo placentas for breakfast and has been Kip’s nemesis for as long as they can remember. Kip is all business as he explained to each of us what our jobs were; there are two other first-timers, and as the only extraneous male I was elected to assist Claude on the port side tack.


A quick aside on tacking. Port=left, starboard=right. Imagine you are sailing north, and the wind is blowing from the east. You’ll have the sail all the way to the left of the boat to go north. If you want to change directions and go south, you’ll have to switch the sail to the extreme right side of the boat as the wheel is cut all the way to the right to catch the wind and change direction. Switching the sail to the other side of the boat to change directions is called tacking. In our race, we followed a short loop north, south, north, and south—each time tacking around a buoy in the middle of the inlet. If you are tacking left to right, the crew on the left side needs to slowly let out slack on the ropes as the crew on the right side feverishly pulls them in. This all needs to be executed precisely with no slack accumulating on the ropes on either side, and needs to be executed as close to the buoy as possibly so you don’t lose any distance. That, in a nutshell, was what we were doing for the day.


It seems simple enough in retrospect, but it was a lot to learn in a minute and seemed like a fairly serious undertaking. Kip’s demeanor was such that it wasn’t quite time to crack open a can of cider (desperately growing warm in the cubby downstairs).


There were two buoys set up about a mile and a half away from each other in the channel leading out of the marina, and the goal was to make the most laps around the buoys before 4pm. That meant we’d be sailing in circles for about three hours, and he who is most efficient at completing that task was the winner. Before I knew it, we were in the water sailing out towards the Great Barrier Reef, and with it, the first buoy. I was asked time and time again if I was comfortable with my responsibilities, and I continually responded confidently in the affirmative. It was one of those things where I’d just need to wing it, and see how I do.


As we approached the first buoy, the atmosphere on board became tense. The plan was to cut the angle around the buoy as tight as we could so we lost as little ground as possible: tighter turns meant less distance covered in one circuit, and less distance covered in one circuit meant more circuits covered in three hours. The ropes were pulled all the way in on the port side (my side) so that the sail was as far to the left as can be. This allowed the wind coming in from the sea to propel us forwards. Immediately after passing the buoy, we needed to tack. It was a tense moment as we passed the buoy, Claude and I holding the rope tight, waiting for Kip’s orders as he told us to “hold it…hold it…wait for it…” and before I knew it he’s screaming, “Tack!! Tack like hell!!” and Claude and I have loosened the cinch and gently let the rope glide through our gloved hands, the extra length being reeled in on the other side while Kip furiously spun the wheel to the port side, switching directions, and suddenly the wind caught the sail and a sense of calm took over the boat. We’d turned around the buoy successfully; the first tack was complete.


Cruising gently in the waters, Kip congratulated us for a job well done. The crew performed admirably, and basked in our praise for a few minutes as we glided across the narrows, at peace with the wind and the sea. There’s something magical about sailing…it’s a harnessing of the natural environment and with it, awareness that for a few minutes, you are, in a weird time and space at one with the natural world around you. It’s a beautiful manifestation of man using the power of nature for a serene pursuit. It was the calm before the storm though, since before we knew it, we were approaching the south buoy, and it was time to get back to our sailing positions.


Things were going to be a bit tighter this time around, and Kip was visibly anxious about executing the turn. Dex Fielder’s boat was about 2 ½ lengths in front of us, which was hardly a comfortable lead, but there was little overtaking on the straightaways and boats were leapfrogging each other only on the turn around the buoy: whoever could execute the tightest, most efficient loop stood the best chance of gaining ground. Needless to say, we were all paying close attention to Kip as the floating marker got closer and closer and closer, until we were maybe a boat and a half off Dex Fielder, gaining ground as we cut inwards towards the buoy, and Kip shouted “Tack! Tack! Pull, you bloody wankers!” and I found myself pulling the rope on the port side with all my might to swing the boom to the left as Kip turned the wheel to the left spinning, spinning and I’m pulling, pulling, pulling like hell, until the rope suddenly became harder to pull since the boom had swung over my head, and the wind caught the sail on the left, and we’ve tacked, we’ve done it; Claude and I could slowly bring the slack in on the rope and secure it with a satisfying clamp. We were now gliding across the smooth water again and had ten minutes to relax and enjoy the scenery before executing another turnaround.


I remember thinking that I could get used to this sailing thing. It was fairly easy as long as your delegated job happened to be that of a simple assistant, and it wasn’t that hard to learn…tack left, tack right, pull a little bit of rope, let a little bit of slack out…how hard could it really be? I thought as I cracked open my first peach cider of the day, looking out across the horizon as everyone enjoyed a moment of melancholy while the afternoon sun blazed down upon us. Kip was enjoying himself, on his third cider already, and Ashley winked at me from her spot on the bow, sharing with me in a single glance the reason she decided to pick up and leave it all behind to spend her days on a sailboat.


The afternoon passed in a series of frenetic tacks punctuated by periods of long calm as we sailed from point to point. As we all became more comfortable with each other as a crew, the tense atmosphere of the first few tacks receded and jovial banter took over as I got to know the rest of the crew-for-a-day on our runs from buoy to buoy. Pete and Jacko were the two guys manning tacking on the starboard side. This wasn’t their first time, but they made for a hearty, welcoming presence to everyone whose first time it was, which included Alex and Sigur, two other friends of Ashley’s. While not an essential member of the tacking crew, Sigur proved quite adept at fetching ciders from the cubby below-decks while everyone else was occupied.


Yet all good things must come to an end, and before we knew it it’s close to 4pm. We had been towards the front of the pack for most of the race, and our placing hadn’t really concerned any of us. No one had royally messed up and Kip had for the most part seemed content with our performance, although he did have a constant eye on the competition where the rest of us lazed. But now we had one, maybe two tacks left before the finish line, and Dex Fielder was 4 or 5 boat lengths in front of us. While there was a few vessels in front of him, it didn’t much matter to Kip where we stood in the overall race.


“We’ve got to catch the bastard”, Kip spit through gritted teeth. Mentally, I perked up. This was go-time, 4th quarter…there was really nothing I could do to help us win here, it was Kip steering and calling the shots, but the overarching motive was to not be the one to fuck up as we approached the south buoy for the final time. Approaching what would be the last buoy, Kip cautioned everyone to wait, wait, wait for it…when suddenly, the rope loosened, just a bit, from the starboard side.


“Jacko, what in the bloody hell are you doing??!”, Kip shouted at our mates on the starboard side. Something was up.


Turning starboard, he agitatedly exclaimed “Pull, pull, pull, now—go, go, go! Tack!!”, shouting at Claude and I…”bloody pull!!”.


Doing as we were told, we pulled with all our might and executed, from our points-of-view, a fairly flawless turn by the day’s standards. The wind caught the sails, and we were off into the straight lane….but Dex Fielder was still a few lengths ahead of us.


“Goddammit!”, yelled Kip. “Jacko, mate, you let go of the rope too soon! I was trying to cut that close enough where we could edge Fielder out and get ahead!”


But it was all over. Kip had wanted to wait until the last second to tack, not letting up any slack as we flew into the turn and cutting things much closer than we had on previous circuits to hopefully eliminate a bit of space between Fielder and us. His mate, however, had other ideas and let slack off the taut starboard side at the same time that we’d been previously doing it, but before Kip gave the OK. This meant we lost forward speed since the sail wasn’t as taut as could be, which is necessary when tacking but it’s all a matter of when you let slack out and loosen the taut line. That little bit of speed lost, in the end, might have done us in. We had to wait another few seconds to pass the south buoy before Claude and I tacked, meaning that we lost a good deal of time. Kip’s ruddy complexion only deepened as his mate apologized for the blown chance, and he drowned his loss at the bottom of a can of cider.


“Oy, it’s not that big a deal, mate. It’s just that Fielder is such a bloody pisser, I can’t stand to lose to that bloke”, said Kip.


We made one last circuit of the north buoy, and the mood was far more relaxed than on the last round. Everyone clearly had a good time, win or lose. The pisser, Dex Fielder, really hadn’t dampened my spirits at all; I’d had a free day of sailing thanks to the gentleman of Wednesday afternoon and Mr. Fielder happened to be one of them. He served admirably as the villain our boat needed: the black flag against which our white could fly brightly, shimmering in the wind like a beacon of freedom, which if nothing else, made for quite an entertaining narrative in my own mind.


Heading back to the docks, Kip thanked us all for our hard work, and said that we’ll get ‘em next week. While unloading the empty cider cans and miscellaneous sailing paraphernalia, we were all invited to dinner at a local Thai restaurant, a 5-10 minute drive away. I continued to help unpack everything—I wanted to be etched in everyone’s memory as a diligent member of the crew, and thus welcome back for another sail should the opportunity arise—and figured I’d wait to ask Ashley and the other kids if they were going before committing to anything. Walking back towards the dock, where the gentleman gather to take the piss out of each other, drink more cider and while away the hours as afternoon becomes evening, I asked her if she was headed to dinner at Caroline’s, and if so, how she planned on getting there.


“Yeah”, she responded. “I’m catching a ride with Desi, though. I rent a room at his place, so I usually ride with him to dinner afterwards…I’d offer you a lift, but you can’t ride more than two on the back of his bike, haha. I’m sure there’s someone around here going that can give you a lift, though. Kip, do you know anyone driving over to Caroline’s that can give Matt and Sigur a lift to dinner?”


“Hey boys”, Kip whistled, “anyone headed over to Caroline’s now that can give these youngens a lift?”.


A short, muscled, Australian with a shaved head, closely resembling Mr. Clean briskly walking away from the crowd turned back and said that sure, he could give us a lift; but he was leaving right now. He cut a vaguely familiar figure, but I couldn’t quite place him.


“Off you go, you bloody bobbers”, said Kip resignedly, shaking my hand and with it, his head.


Sigur and I followed Mr. Clean towards his car, while I quickly introduced us and thank him profusely for his generosity. Mr. Clean extended his hand and in a most affable manner drawled “Pleased to meet you, mate. Dex Fielder. How’d your sail go?” I guess he wasn’t not such a bad guy after all.