“You can hold onto my foot if you need to.”

Bill’s boat shoe dangled above my head as I clung to the lifeline cable, looking directly up at the cockpit, which was pitched at 90 degrees above me. The lower half of my body was submerged in San Francisco Bay, being dragged along at about 8 knots. A sudden tiller correction had caused the boom to swing wildly to port, heeling the boat over violently — what sailors call “rounding down”. I happened to be crawling along the low side rail after hoisting the spinnaker when this occurred, sending me into the water. Despite the chaos above me — skipper Nick shouting for corrections, crew members scaling the deck to ease sheets — I was calm, expecting to see the boat complete its rollover and send everyone into the Bay along with me. But a 4,000-pound lead keel doesn’t give up that easily and slowly the boat righted itself; I crawled back on deck, dripping like a wet cat, and started loading the jib sheet winch.

MORE HIGH SEAS ADVENTURE: Sailing with Team Alvimedica | Classic Yacht Racing In Marblehead | The America’s Cup

The Rolex Big Boat Series is known by participants as the “Break Boat Series” for the toll it takes on boats and crews over four days of racing. San Francisco Bay in September is notorious for its shifting gusty winds and strong tides. Combined with heavy cargo ship traffic and a crowded fleet, this is one of the most challenging weeks on the North American yacht racing calendar, and one of the most popular.

Avast! Awash! A Cheat Sheet to Sailing Terminology

Sailing has a bewildering language all its own. On a sailboat, there is no left or right, no ropes and no floor, and to use any of those terrestrial terms will instantly identify you as a landlubber. Here’s a key to some nautical terms so you can sound like a sailor, even if the only sailing you do is in the bath tub.

Port: the boat’s left side.

Starboard: the boat’s right side.

Jibe: when sailing downwind, a change of direction that swings the mainsail boom across the boat.

Tack: to change direction when headed upwind by moving the jib sail to the other side of the boat.

Heeled over: when sailing upwind, the boat is pitched at an angle, putting one of its rails closer to the water. Crew counteracts this by sitting along the high side rail, a move known as “hiking out”.

Halyard: the rope that passes through a pulley at the top of the mast and is clipped to a sail to raise it (the mainsail, jib and spinnaker each have their own halyard).

Sheets: the ropes used to trim, or tighten up, the jib, spinnaker and mainsail; on larger boats, trimming is done with the aid of a winch.

Jib: the front sail used when sailing upwind. Different jib sizes are used for different wind conditions: a smaller sail area when wind speeds are high, larger for lighter breezes.

Spinnaker: the huge “kite” sail that is deployed when sailing downwind to capture the most wind possible.

Deck: the horizontal top surface of a boat.

Keel: the blade that hangs below the hull of a sailboat, usually with a heavy bulb of lead at the bottom to counteract the wind in the sails and keep the boat upright.

Tiller: the handle that is attached to the rudder and used by the skipper to steer the boat.

Knots: a speed measurement on water: 1 knot equals 1.15 miles per hour, so 30 knots equals 34 mph.

2014 was the 50th anniversary of “Big Boat”, and a huge contingent of boats came to compete in ten different classes, each vying for the coveted Rolex Submariner that would be awarded to winning skippers. There were massive 65-foot multihull rockets and tiny 22-foot J/70s racing; but the rock star boat class in the Big Boat Series is the Farr 40, a gorgeous vessel from the famed Farr Yacht Design, who also penned this year’s Volvo Ocean Race boats. No less than 15 Farr 40s lined up each day to tack for position ahead of the start cannon, and when their spinnakers were unfurled at the upwind mark, the fleet was a thing of beauty passing under the Golden Gate. The different boat classes were sent off in five-minute intervals on three courses around the Bay, for two races a day. That many boats under sail made for some hairy near-misses, with many a call of “Starboard!” shouted to remind charging vessels of the right-of-way.

I was crewing on Escapade, an Express 37 boat, and after Day One, I lost any illusion that yacht racing is a genteel sport for rich old guys. Escapade is sailed by a young crew, an eclectic bunch of bike mechanics, PhD’s and entrepreneurs. Despite some success in one-day buoy races, this was Escapade’s first entry in the Big Boat Series, a test of both the boat’s mettle and the crew’s, in a class of seven boats, many with seasoned professional skippers and experienced crews. My position onboard was, at the mast, “jumping halyards”. This job kept me largely out of trouble, more brute force than strategic thinking or a knowledge of knots and race tactics. In the Age of Sail, the largest crew members literally jumped off the ship deck and pulled down the rope, or halyard, as high and possible, and pull down to raise the sails. While no jumping was involved on the narrow, slippery deck of Escapade, hoisting a jib quickly still involves technique, which I painstakingly (and painfully) learned. Grab high on the halyard, lean back to pull and bring the line in close to the mast before doing it again and again. The key is to get the sail up quickly to minimize the risk of twisting or entanglement and to maximize the amount of Kevlar that catches the wind when rounding a course marker. Easier said than done on a slippery boat deck heeled over in the wind.

My nightly routine became counting new bruises and popping Advils with a cold beer. Break Boat indeed.

On Escapade, we had our hands full and after a promising 5th place finish in the first race; in the second race, a sizable tear was discovered in the #3 jib midway through, in gusty 20-knot winds. We lowered sail and limped into the marina, failing to finish but mitigating further damage and living to sail another day. An emergency sail patch was undertaken that night; but the following days saw further tearing in the jib, a hole in the spinnaker, jammed winches and handles lost overboard to the depths of San Francisco Bay. Our crew was faring no better. Cries of pain could be heard on almost every hard tack as soft tissue met with unforgiving wood, metal and fiberglass. My nightly routine became counting new bruises and popping Advils with a cold beer. Break Boat indeed.

Day three started out eerily calm as we motored out to the start area. Escapade was battered but optimistic. A bad start and late jibe on a downwind leg foiled our chances for a good finish in the morning race. We found ourselves wolfing down sandwiches in a stiff 20-knot wind between races. The second race would require smaller sails for more manageable sailing in the building gusts. We had a good start, tacking upwind alongside the other Express 37s all the way to the Golden Gate. Rounding the marker, I struggled to hoist the spinnaker in the strong winds and we headed back towards Alcatraz. By now the wind meter was flirting with 30 knots and our bowman was being punished by spray as he crawled around the foredeck. And then we rounded down and I went into the water.

An Ironic Casualty of Rolex Big Boat Series

Rolex-Sidebar-Gear-Patrol

Being it was the Rolex Big Boat Series, naturally I wanted to wear my own trusty Submariner while crewing on Escapade. I fitted it with a nylon NATO strap to avoid losing it to the Bay in the event of a spring bar failure. On the second day of racing, during a particularly grueling hoist, I felt my wrist snag momentarily on the tensioned mainstay cable but thought nothing of it. Perched on the rail later, I glanced down to see my watch’s bezel was gone and a fresh scratch on the left side of the case. A crew member crawled across the deck and handed me the bezel, which I tucked into a pocket for later refitting. The ratcheting click spring was lost to the depths, but no matter. My Rolex had another story etched into its history — a casualty of the Big Boat Series.

Nick said later that he didn’t see the tip of the mast quite go under but later confided he was glad he recently resealed the cabin windows. Once we got Escapade righted, the spinnaker was doused and we limped across the line, everyone happy to have not gone swimming. The prospect of a cold beer back at the dock was that much more appealing.

That night, Mount Gay Rum hosted a party on the lawn outside the St. Francis Yacht Club, complete with Dark and Stormies (rum and ginger ale) and a steel drum band. The Escapade crew, sunburned and bruised, wolfed down finger food and recounted the day with laughter and relief. Harsh words shouted in the heat of battle were forgotten. Crew member Johnny, with his dreadlocks, was mistaken for a member of the band by a white-haired yacht clubber. Much rum was drunk, which eased the pain of my broken body. I had vowed that, as the outsider to the crew, I would not be the one to fall overboard. And I succeeded. Mostly. This would be my last day on the boat; I opted for a spot on the photography chase boat for the last day of racing. Now I was regretting that decision. I wanted to be out there again.

Big Boat Series may be about breaking boats and bruising crews, but it’s also about forging a team. Despite the hardships and, yes, the danger, Escapade would be out there again tomorrow, and next year, lining up against the other boats, heading upwind towards the Golden Gate.