Second Wind: A Nantucket Sailor's Odyssey

by Nathaniel Philbrick

  Into the Maelstrom

  I AWOKE LATER THAN I had wanted. When I emerged from Spars and Bars, the Sailing Squadron’s parking lot and lawn were bustling with activity. Boats were being unloaded, sails raised, old friends were shaking hands and slapping backs.

  I had about an hour before I had to leave the beach. Soon I was off in the far corner of the club lawn and fiddling with my sail. These new sails were different. Besides having a fuller and more powerful shape, they were made out of heavier, more durable cloth. By the time I headed for the clubhouse to fill my water bottle, I wished I had arrived a day earlier just to sort out the new variables.

  The bulletin board announced that 104 boats had registered for the regatta, making it the biggest Midwinters on record. This was a long way from sailing by myself on a pond on Nantucket. I was making my way through the crowded parking lot when a white Lincoln Continental with a Sunfish on the roof pulled up and parked right in front of me. Through the tinted windshield I could dimly see that the driver was waving at me. It turned out to be Alan Scharfe, an old friend with whom I had roomed at the Sunfish Worlds in Puerto Rico in 1978. At one point during that regatta the two of us were in the hotel elevator on our way to dinner. Suddenly the elevator lurched to a stop, and for the next hour we were trapped in a tiny, humid, and very hot box. The highlight of our confinement occurred when the hotel custodian told us “Don’t go anywhere” while he went for help. Over the last fifteen years I’d seen Alan a handful of times, and each time one of us inevitably retold that story.

  Now a successful electrical contractor in the Boston area, Alan, despite a laid-back, affable manner, was a top-notch racer who regularly finished in the top five of the world championships. As I helped him unload his boat, he asked where I was staying. It turned out he had booked a room in the Holiday Inn at nearby Lido Key, and he offered me his room’s sleeper sofa.

  “Hey,” I said enthusiastically, “it’ll be just like the Worlds in Puerto Rico!”

  Alan smiled. “Yeah, remember that time when we got stuck in the elevator. . . .”

  It was a perfect day for a sailboat race, with blue skies and a ten-to-twelve-knot breeze. The massed fleet heading for the starting line looked like a giant flock of migrating birds. There were Sunfish ahead of me, Sunfish behind me, Sunfish on every side. I was awestruck and slightly baffled. A horn sounded and a yellow flag rose—ten minutes before the start. My watch had hands instead of a digital display, making it difficult to keep track of how many minutes I had left. In an instant I felt the full impact of my unpreparedness.

  What made it all the worse was the memory of how it used to be. Instead of a blur of boats, I used to see a fleet of individual competitors. Instead of wallowing in aimless confusion, I had studied the fleet like Nelson, assessing every possible advantage. I had been in command. Now I was just an ordinary seaman.

  With one minute to go, I was so jacked up on adrenaline that I could barely hold the tiller. I saw a hole on the leeward end of the starting line, opposite the committee boat, and went for it. I trimmed in the sail and then—no starting gun. I had screwed up the time. There was still one minute to go. So there I was, in the worst possible position. I had already crossed the starting line and now I had only a few precious seconds to find a place on a starting line that was already jam-packed. As I jibed around the buoy end, I saw nothing but boats.

  By the time the actual starting gun fired, I was back in the third row. This was not how I’d envisioned my first regatta. The first row of boats jumped out and were off, leaving the rest of us to find some leftover wind. No matter where I went, there was always a boat almost directly ahead of me, its sail sucking away my air. I was mired in the back of the fleet, unable to pass the kind of people I used to eat for breakfast and even being passed by some of them.

  One elderly gentleman with a wide-brim hat and a Hawaiian shirt was particularly annoying. Here I was in my state-of-the-art lifejacket, boots, and sailing gloves, looking like I should be going fast, and yet, dammit, this joker was making me look like a fool. After we traded tacks for the last half of the beat, he rounded the windward mark just ahead of me.

  It was an ego-shattering experience. All my fears, worries, and insecurities came bubbling to the surface. This was exactly the nightmare I had hoped to avoid. In the distance ahead, the leaders were anonymous speedsters, masters of skills that were now beyond me. Then I began to notice that along with the guy in the hat and Hawaiian shirt, there were more than a few young bucks in my vicinity. I wasn’t the only guy in the back of the pack wearing an expensive lifejacket.

  I eventually finished fifty-fifth, smack-dab in the middle of the fleet. Going into this regatta, I had dared to think that I might be able to at least challenge the leaders. At this point, I wasn’t even in their league; I couldn’t even see who they were.

  The next race was considerably better: I finished in twenty-fifth place. Still, I had no sense of mastery or accomplishment. I had no sense for what was happening with the wind shifts. Instead of thinking two tacks ahead, I was reacting to situations that I should never have allowed to develop. I had made two mistakes that required me to sail penalty circles. My sailing was messy and out of control. As I sailed back to the club, I thought seriously about catching an early flight back to Nantucket.

  It didn’t get any better when Alan, who’d finished a respectable seventh in the first race, greeted me at the scoreboard inside the club by asking, “What happened?”

  “Isn’t it obvious?” I wanted to snarl. “I suck!” But after taking a deep breath, I tried, as best I could, to explain what had indeed happened.

  Roll Call

  I BEGAN TO CLIMB out of my Slough of Despond that evening as Alan and others introduced me to the current breed of Sunfish sailors. The fastest sailor of the day had been Bob Findlay, who had amassed an impressive record over the years, winning the Midwinters a total of five times while also doing well in Laser and Hobie Cat championships. Of my generation, with a wife and a couple of kids, Bob was proof that having a family and winning major Sunfish regattas were not mutually exclusive.

  The Midwinters was dominated by the presence of master (over forty years of age) sailors, who accounted for more than half the fleet. In addition to these “confirmed” master sailors, there was a large group of “emerging” masters—sailors my age or slightly older who had either stuck with it all these years or were, like me, just getting back into it.

  I began to attach names to all those anonymous boats, and what struck me was the remarkable diversity of the Sunfish class. Most singlehanded classes are raced by strong young men in their twenties. For example, racing the Laser competitively with a full sail in a decent breeze requires a body weight of at least 165 pounds and excellent physical conditioning. The Sunfish, however, is a different animal. Thanks to its chines, its hull shape is more stable than that of the round-sided Laser. The Sunfish’s untraditional rig, while it may look strange, is efficient and adaptable enough to allow lighter-weight women and children to remain competitive, even in high winds. There is no other sailboat as inexpensive and light as the Sunfish that can be effectively raced by such a wide range of people.

  At the Midwinters there would be eight master sailors and four women in the top twenty; the top junior (sixteen years and under) would finish twenty-third. Those gathered around the keg at the Sarasota Sailing Squadron that Friday evening were the kind of people you might see at a community barbecue—fathers, mothers, kids, single professionals, not to mention plenty of grandmothers and grandfathers.

  After moving out of Spars and Bars, I followed Alan to the Holiday Inn. He had a spectacular top-floor room overlooking the Gulf of Mexico. That night we had dinner together at the hotel restaurant, and Alan, a newly retired Sunfish Class president, filled me in on the class’s recent history.

  The eighties had been tough on the Sunfish and on sailing in general. What had been a truly grassroots sp
ort in the sixties and seventies began to lose people right and left. Many young kids traded traditional “sit down” classes like the Sunfish and Laser for “stand up” craft known as sailboards or Windsurfers. Other sailors traded in their sailboats for motorboats because they were easier to use and didn’t require a crew. More than a few sailboat manufacturers went bankrupt. AMF, the giant conglomerate that had bought out Alcort, the Sunfish’s original builder, back in the seventies, decided to get out of the boat business.

  Although attendance at major championships had diminished throughout the 1980s, the Sunfish was now, according to Alan, poised for a comeback. For one thing, the class had a new and committed builder. For another, pockets of regional activity had demonstrated remarkable strength in recent years. While New England, once the stronghold of the class, had begun to fade from the forefront, the Midwest and especially the Southeast were stronger than ever. This Midwinters’ attendance by “Team Florida” from the state’s west coast was particularly impressive. And finally, there were baby boomers like me who were finding their way back to the boat of their youth. That night on the sofa bed, I began to think about the day I’d just had and the day that lay ahead. Even though I had experienced a past champion’s worst nightmare, perhaps it was for the best. Certainly, I assured myself, it couldn’t get any worse.

  Over Early

  SAILING OUT TO the course the next morning differed completely from the day before. For one thing, I’d begun to recognize the people I had known in the old days, and it was startling to realize that they still sailed with the exact same posture of fifteen years ago. Things were beginning to seem almost familiar.

  I had an okay start in the middle of the line. Nothing inspired, but sufficient. The wind was lighter than the day before, and it would continue to drop throughout the race. Although I was a long way back from the leaders, I wasn’t completely out of touch, and I made a point of watching them as they rounded the leeward mark at the end of the first triangle. I wanted to learn anything that might prove useful.

  Once again it was Bob Findlay in the lead. He was immediately recognizable as the person who moved the most in his boat. Even though the wind was relatively light and he was barely able to sit out on the deck, he was constantly jumping around his boat and adjusting the mainsheet. Watching Bob made it clear that I was still a relative stick-in-the-mud. While most of us were just sitting there, Bob was a virtual perpetual motion machine, and yet there was a subtlety, even a delicacy, to his movements. This guy was going to be very tough to beat in Springfield.

  I ended up finishing twenty-second. Not great, but my best finish to date. It turned out I was in good company, amid a cluster of past champions and contenders. This was a very tough fleet. There was no reason for despair.

  Eventually the breeze died down to a near dead calm. For the next few hours we waited for wind and ate lunches provided by a support boat. For the most part, I hung out with Alan. It was very companionable, bobbing there side by side on windless Sarasota Bay with our legs sprawled across the decks of our Sunfish as we lay back in our cockpits, our tiller extensions resting on our shoulders, and talked. All the gabbing had a soothing, revivifying effect. By the time the wind had risen to the point that the race committee felt they could attempt another start, I had decided that this was going to be my race.

  Others seemed to have the same idea. As time wound down for the start, it became obvious that a large portion of the fleet was going to be over the line early. The race committee was forced to recall the fleet and begin again. This had already happened a few times before, and the race committee raised a black flag to indicate that any boat venturing over the line with less than a minute to go before the next start would be automatically disqualified. This had the desired effect, and the start proceeded without a hitch.

  I nailed a magnificent start on the windward end of the line. It was the kind of start I used to manage on a fairly regular basis. How different things seemed from up here on the edge of the fleet! Now it wasn’t a question of clearing my air; now it was a question of consolidating my position up here in the stratosphere. I was walking across a high wire; one misstep and I would tumble down into the fleet below me.

  Should I tack, or should I keep going and try to stay with the rest of the fleet? I began to panic, but in an entirely different way from that first race the day before. In a certain sense it was a kind of stage fright. Here I was, caught in the spotlight, and what was I supposed to do? I told myself that the secret was not to try too hard. Regattas weren’t won by being brilliant. No, they were won by not messing up. I should sit back, go fast, and let the rest of the fleet make the moves, positioning myself so as to minimize any potential damage from wayward wind shifts. I must clear my head and go with the percentage move. I didn’t need to be first; I just needed a decent finish.

  Unfortunately it was an awfully big course, and from my starting point over on the committee boat end, it was difficult to keep in touch with those who had started over on the leeward end of the line. And as fate would have it, the other side of the course ended up paying off. Still, I ended up fourteenth. On the way back to the club I was jubilant.

  As I approached the club I could hear the throbbing bass of a rock band warming up for the regatta party scheduled for that evening. My in-laws, Marshall and Betty Douthart, were on the pier videotaping the fleet as it sailed into the club. On the tape I at least look like one of the fast guys—the sail low and boom cocked up at a rakish angle, my sunglasses giving me a vaguely threatening appearance—Pondman goes tropical. The best part of the video shows a great mass of boats well behind me.

  After a brief chat with my in-laws, I made my way to the scoreboard. Alan was already there. He was shaking his head. When he saw me, he laughed and slapped me on the back.

  “Join the club,” he said.

  Instead of having just scored my best finish of the regatta, I’d scored my worst. I had been over the starting line early in the fourth race, and as a result I’d been disqualified, adding more than one hundred points to my score. Even if we were allowed to throw out our worst race, which would happen if seven races were completed, I’d have to count my horrible first race. As it stood, I was in fiftieth overall.

  But Alan helped me put it into perspective. He had also been a victim of the black flag, not once but twice. We couldn’t believe it. Weren’t the hotshot young kids supposed to be the ones who were called over early?

  After I’d gotten over the shock of what it had done to my cumulative score, I almost began to enjoy the fact that I’d been over early. It was a badge of honor. “How’d you do?” someone would ask. “Over early in the fourth,” I’d reply with a knowing smile. It was like getting caught for speeding on the highway—the price of living on the edge, being footloose in the fast lane.

  I was able to sustain this macho denial for only a few beers. By the time I returned to the hotel for a shower, I was cursing myself for pushing it at that start. There had been no need. But tomorrow would be another day, and now I had nothing to lose.

  What Ifs

  AS WE SAILED out to the course on Sunday, I felt numb. Here I was, into my third and last day of the Midwinters and I was in the precise middle of the fleet. Two months earlier, I would have been horrified at the thought. So why didn’t I even seem to care?

  The wind was light. Since they wanted to sail three races, the race committee got things off quickly. I managed a reasonable start in the middle of the line and came in twentieth.

  The next race marked the first time that I felt like I might be able to sail at my old level. I finished eighth and was, for a change, not losing boats toward the end. Bob Findlay won, virtually assuring him the regatta win, and the race committee decided to go for one more.

  My expectations were high, but at this stage I just didn’t have what it took to break into the top five. I finished fifteenth. Once again, it was not a bad showing in relation to the ove
rall standings, but it was not the phenomenal finish I had been yearning for.

  After packing away all my stuff and venturing back to the clubhouse, I was astonished to see that my day’s racing had taken me from fiftieth to twentieth overall! I did a few “what if” calculations. If I hadn’t been over early in the fourth race, I’d have ended up around twelfth overall. If I had maintained my third-day average throughout the series, I’d have cracked the top ten.

  I’d been through a three-day process of spiritual breakdown and reconstruction, a necessary catharsis if I was going to approach the North Americans in four months with any hope of doing well. I now had a whole new laundry list of goals and objectives, and above all, I now realized that the ponds on Nantucket, each with its own peculiar demands, were very appropriate practice waters. It was not strength and endurance I needed, but sensitivity and smarts.

  Unfortunately, Alan was not going to be able to sail in the North Americans. We both agreed that seeing each other had been the highlight of our Midwinters. Neither one of us had done as well as we had hoped, but as Alan reminded me, “This time we didn’t get stuck in an elevator.”