I have a few years of sailing under my belt and have become a competent helmsman and crew member, but my experiences have been invariably mild. Rarely do I set out with a looming dark cloud anywhere in sight. In fact, few occasions have found the day to be even overcast. I have sailed primarily out of the Milwaukee Sailing Center where the boats are well maintained by full time staff so while I had never found myself in inclement weather, I had never found myself with any real problems to deal with while underway either.

Braveheart’s skipper had told me early in the season of the Queen’s Cup and it sparked my interest immediately. This would be a true test of my commitment to sailing. I’m an admitted dreamer and often find that my idealization of any particular thing is often much less mystical than the actual doing of the thing. Regardless, after his mention of the race, my mind set to work on imagining an adventurous night time crossing of a wild and treacherous sea.

On race day, my wife drove me to the yacht club and watched as I loaded my provisions into the cart which was already mostly full with large cases of beer, comprising the majority of my crewmates’ supplies. We pushed the cart and hauled the excess items on our backs and shoulders down to the docks where the tender would deliver us to our vessel.

The crew made quick work of loading the boat and within a quarter hour we set off for the start. After leaving the breakwater from the south gap of Milwaukee marine area, the seas grew mildly taller, tossing an occasional spray up over the bow. Some minutes into the push out to the starting area, it began to rain. My crewmates and skipper quickly went below leaving me at the helm.

Alone in the cockpit, staring into nothing but open water, a barely discernable horizon, and a faint rainbow to the southeast, I felt a stirring hint of the adventure I had imagined. The tiller was stiff and resisted my suggestions of any slight correction, but our course remained ostensibly in tact. The rain was falling hard now and those below slid the companionway hatch closed. I was getting soaked to the skin, but I was happy to continue my imagined adventure to the East, alone in my own vessel, pounding through waves in a formidable blow, a true blue water sailor.

No sooner had my adventure begun when the hatch slid open and my crewmates sprung back into the cockpit, donning yellow and red rain gear. Each found positions and I fixed myself to the stern rail manning the mainsheet. The rear of the boat provided some delusion of control as everything that was happening aboard the boat was happening in front of me. I have found that in my increasing age, my tolerance for surrendering control of my own destination has produced an abundance of anxiety. As it turned out, this trip would not only test my grit as a sailor, but also test my boundaries between comfort and paranoia.

After motoring to the general vicinity of the starting line, we hoisted our mainsail and reviewed the instructions for the start. Since our boat lie in the highest handicapped division, we would be starting at the first gun. Next we unfurled the Genoa and sailed close hauled toward the start. The Dennis Sullivan, a three-masted schooner looking like something sailed by the Royal Navy during the American Revolution, would serve as the windward side of the starting line. Very soon after we got our bearings of where the starting line actually was, the cannons from the Dennis Sullivan exploded, sounding just like something out of an old pirate movie. It was an impressive sound, and an impressive scene. Never before had I seen so many boats in such a small area tacking, jibing, hoisting, and drinking.

Cannon shot rang out, and with no awareness about me, the skipper said “we’re racing boys”.

The wind was coming almost directly from the South. Our finish line lie 68 miles due East. This wind bode favorably for Braveheart as she had no spinnaker to fly, and was handicapped to prove it. Although the other vessels had spinnakers, this particular wind bearing provided little hope of actually flying it. One would have to close reach to the South on a relatively steep heading to fly a spinnaker on a Northerly heading. Since the beam reach is on average the fastest point of sail for any boat without a spinnaker flying, it was up to us to make the most of our advantage and sail our course as close to the line as possible.

As the excitement of the race start began to give way to the reality of our position I gazed back at the fading skyline of Milwaukee. The sun broke just below a dark band of clouds in the nick of time to present a gorgeous sunset. Silhouettes of masts pitched in the foreground while the sun illuminated the sky behind a quickly shrinking cityscape. The water off the stern was a stunning collage of dark blues and greens. I snapped pictures of the gentle wake streaming just off Braveheart’s stern, but those pictures appeared rather silly later I found.

Next installment to come... The Overnight