Second Wind: A Nantucket Sailor's Odyssey

by Nathaniel Philbrick

  PART III

  The Swift Monster

  For as the swift monster drags you deeper and deeper into the frantic shoal, you bid adieu to circumspect life and only exist in a delirious throb.

  —HERMAN MELVILLE, Moby-Dick

  Oedipal Sailing

  IT TOOK ME A WHILE, but gradually I began to figure out that most of my problems in Florida had had little to do with sailing and a lot to do with me. It wasn’t until I’d been home for a few weeks and was back into writing the book that I realized just how out of whack I’d been in Sarasota.

  It all came down to family. Without my wife and kids, I’d been a wire stripped of its casing; I’d been a “primary caregiver” who was no longer primary and hardly without a care. I’d been a basket case.

  I thought back to that blessed event—the 1978 Sunfish North Americans—which still loomed so large across the years. It had been sailed in Barrington, Rhode Island, the same little town in which my father had summered as a boy. Our family had spent the week of the races in my grandmother’s summer home, a wonderful and familiar little place less than ten minutes from the regatta site. Instead of being a lone wolf in the wilderness, I’d had the ultimate support system, enabling me to unwind each night within the warm and welcoming bosom of my family. Looking back, I wondered whether I’d won the regatta not because I was the best sailor but because I’d had Mom to cook dinner for me every night.

  The more I thought about it, the more I realized that sailing had always been inextricably tied to family, and any attempt to separate the two would be like setting up a Berlin Wall across the interior of my brain. But how in God’s name was I going to convince Melissa, Jennie, and Ethan to come to Springfield, Illinois, in July?

  It was Sunday, March 21. It had been two weeks since I’d returned from Florida, and I was deep within, if not the bosom of my family, at least the interior of my parents’ car, driving down Route 6 on Cape Cod in a dank, Stinker-like vehicle full of sailboat equipment. Melissa and the kids were attending Jennie’s swim team finals at Massachusetts Maritime Academy. I’d been granted a reprieve so I could sail with my parents, who were now retired and living just across Nantucket Sound near Hyannis, the mainland ferry terminus that is to Nantucket what my parents had once been to me—the source of supply, the lifeline to the world.

  I’d always assumed my parents would go the way of most sailors; that they’d move on to bigger and more comfortable boats as they entered their golden years. Instead they turned to the six-foot-four-inch Cape Cod Frosty, which, in addition to being the smallest racing class in the world, is (as the name might suggest) sailed only in the off-season. The Frosty is an absurd matchbox of a boat that forces an adult sailor to become a contortionist just to fit into it. After an hour, both knees are on fire and the back throbs. But for masochists it’s fun, and since my parents had an extra boat, I decided to go Frosty sailing. Besides, in the Philbrick family the best way to visit is if a sailboat of some kind is involved.

  So with two boats on the trailer, one on the roof, and me stuck in a backseat jammed with sails, rudders, and other equipment, we headed for Wychmere Harbor, a tiny anchorage in Harwichport. My parents are nothing if not punctual, and we were the first ones there. It was a gray, rainy, light-air day, and soon the rest of the fleet began to arrive.

  This was the first race day of the spring season, and a series of winter storms had inflicted its share of damage on the Wychmere race committee “boat,” a little dock-mounted shack that had had its roof and windows blown off. Fortunately, the section of roof and even the window were found on a nearby shore, and with the help of a hammer and nails, repairs were effected in a matter of minutes.

  There were ten of us, including “Poppa Frosty,” Tom Leach, the Harwichport harbormaster who had invented the boat back in the early eighties. Tim O’Keeffe, a past Frosty North American champion, was also part of the group, but with many of the fleet having the last name of Philbrick, this was destined to be something of a family affair.

  In the old days my mother had always been a relatively reluctant sailor. Traumatic memories from her youth (her father used to yell at her through a bullhorn when she raced her Beetle Cat) kept sailing from being her first love. My father, on the other hand, had been a champion sailor, and as a young parent he had taken to Sunfish racing with obvious relish. In fact, in my adolescent days, when I was going through all sorts of hormone-induced tirades, I developed a mental block when it came to racing against my dad. Even though I had progressed to the point that I should have been able to beat him relatively easily, I always seemed to mess up if the two of us were on the same race course. I’d find myself unnecessarily obsessing about where he was, and sure enough, Pop would always end up passing me at the finish.

  Eventually my brother and I moved into the “470,” a two-person, Olympic-class boat, and then came college. When I came back to the Sunfish during the summer of my junior year, I was pleased to discover that my father phobia had passed. I could now sail in the same race with him and not find myself constantly looking over my shoulder.

  I will always remember one race in particular during the Sunfish North Americans in Barrington. It was early in the series, and I was fighting it out for first overall. Both my father and my brother were in the championship fleet. The wind had built up to twenty knots. I was in my element; my father, a light-air expert but definitely no heavy-air animal, was out of his. We had already sailed three races that day, and one more was scheduled. The fleet was lining up for the start. I was planing down the line, looking for a hole. I saw my opportunity and went for it, belatedly realizing that I was setting up to windward of my father.

  So there we were, side by side with thirty seconds to go. I remember feeling several different emotions. First I felt a sense of reassurance. I knew that Pop must be totally exhausted; indeed, he was just the kind of guy I wanted to leeward of me because I knew I could grind him into the dust. I also felt guilty. How could I trample all over my own father? And then as the seconds wound down, I found myself going through the same motions I would have gone through with anyone else, hitting the line at full speed, rounding up, and sailing over him almost immediately.

  I won that race, and looking back, it was the race that turned the series around for me, giving me the confidence to hold off the competition until the bitter end. Pop and I have never talked about that start, but it still stands in my memory as the moment when I finally put all the tortured agony of my adolescence behind me.

  In his retirement my dad has established an extremely consistent record in the Frosty. My mom, on the other hand, has always been a wild card. Sometimes she can surprise you, coming out of a far corner of the race course to finish unexpectedly well. Just as often she opts to remain onshore, reading in the car rather than getting rained on in a Frosty. This day, however, despite the occasional drizzle, she sailed all afternoon.

  We sailed five races. Maintaining the bad habits I had acquired in Sarasota, I was over early in the last race, and finished third overall. The winner? My mom! She put us all to shame, combining blazing boat speed with smart, conservative tactics. After the second race (which she won), she sighed and announced, “Well, now I can die content.” For “serious” racers such as my father and myself, my mom’s carefree approach can be frustrating. While we were beating to the finish, and I was consumed with trying to catch a favorable shift on the left-hand side, she asked how my book was coming. By the end of the day I’d begun to suspect that my mother’s questions were not as ingenuous as they at first appeared.

  Perhaps the best race was the third, in which Mom, Pop, and I finished first, second, and third. At the awards ceremony held in a local bar, there were a lot of snide comments about that race, with several unsubstantiated accusations of team racing. Mom silenced the critics by ordering onion rings all around.

  That night, after meeting up with Melissa and the kids at my parents’ home, we
took the late boat back to Nantucket. We’d brought our car with us, and since it was already 8:30 we decided to stay below on the freight deck rather than venture up to the passenger section. As Melissa read in the passenger seat, and Jennie, Ethan, and Molly the dog slept behind us, I scribbled notes about my day of Frosty sailing.

  Pop was too honest to be entirely gracious in defeat; although he had been pleased by Mom’s performance, he couldn’t help but be disappointed that he hadn’t done better (he finished fifth), and he’d talked about making changes to his Frosty’s hull. I thought about how my love of sailing and my career as a writer could all be traced in various ways to my father, a retired English professor whose specialty is James Fenimore Cooper and American maritime literature. Only then did I realize how early I’d begun to soak up his passion for racing sailboats.

  When my brother and I were very young, Pop told us a bedtime story that I have never forgotten. My father’s older brother Charlie had been a fierce competitor in the Beetle Cat class, ultimately winning the junior championship in 1939. Charlie would go on to become a fighter pilot in World War II, then a prizewinning poet before dying of cancer at a tragically early age. For my father, Charlie would always embody a swashbuckling, win-at-all-costs recklessness that on a summer day in the late 1930s almost got him killed.

  The morning began with a flat calm, and figuring that he wanted the lightest crew he could find, Charlie decided that his younger brother Tommy, not even ten years old, should sail with him. The race began with light enough winds, but inevitably the sea breeze started to build. It wasn’t long before Charlie and his pipsqueak crew were hopelessly overpowered. But Charlie, cursing and cajoling, pushed on. My father was terrified.

  Then, in the midst of the race, a wave brought them down on the submerged tip of a stake marking an oyster bed. Even though it punched a hole into the boat’s wooden bottom, Charlie wasn’t about to give up. Ripping off his shirt, he insisted that little Tommy stuff it into the hole and hold it there. As water bubbled into the boat and my father tossed from side to side within the sloshing confines beneath the Beetle Cat’s deck, Charlie sailed his sinking ship on. Remarkably, they finished the race in second, but for Charlie it had been a disaster. They hadn’t won, and it was all Tommy’s fault.

  Unlike my mother, who knew enough to tell her father to go to hell when it came to racing sailboats, my father followed in his charismatic brother’s footsteps despite, or perhaps because of, the early trauma he had experienced. My father is one of the sanest men I have ever known, except when it comes to sailing. It inspires in him, as it does in me, a Charlie-like frenzy, a state of madness in which all the passions we otherwise dare not express spill forth.

  Sailing has always been for the Philbrick family a competitive endeavor, and I now wondered whether on the starting line of that pivotal race in the Sunfish North Americans I had unconsciously assumed the role of Charlie, the dominating and remorseless older brother.

  Leaving Hyannis that night, deep within the belly of the ferry headed for our Nantucket home, I wrote: “Pop is a guy whom I greatly admire and try to emulate and, ultimately, try to beat. There, I said it.”

  The Prop

  IT WAS SPRING, and I was back to sailing Nantucket’s ponds. With the Midwinters behind me, I discovered I had a very different approach. This was now less a cosmic journey into the bleak kettle holes of my soul and more a weekly practice session for an upcoming regatta, a regatta that was now only three months away.

  The day was cold and gray, a throwback to winter, as I drove out toward Madaket with Melissa and the kids. Across the street from Long Pond was Head of Long Pond, a roundish open pool that seemed suitable for a no-nonsense hour of training. I knew the weaknesses I needed to work on: mark roundings, tacking, and jibing—the essentials of boat handling. I also knew that I lacked the “one-with-the-boat” sensitivity that only time on the water can ingrain.

  This time I had a prop—an old Clorox bottle tied to the head of a pickax. When I threw the rusted piece of iron into the Head of Long Pond, the clothesline following it down and the white buoy bobbing on the gray water, I felt a new sense of purpose. Gone were the days of relatively aimless exploration; now I had a focal point around which to organize my training session.

  I practiced leeward mark roundings. Over and over again I approached the Clorox bottle on a run, working out the precise angle required to bring me within a whisker of the buoy as I headed up onto a beat. I performed rapid-fire tacking and jibing drills, to the point that I began to sweat. By the time I returned to shore, where Melissa and the kids waited in the car, I felt I had made a small but measurable advance toward preparing for the North Americans.

  And yet something was wrong. I had been on my pond and they had been in the car. I could see what lay ahead: The more focused I became in the succeeding weeks, the more isolated I would become. If this comeback was going to count toward anything, it would have to somehow involve Melissa, Jennie, and Ethan.

  Unfortunately, the last thing they wanted to do was tag along to Springfield. Unless you are participating in it, there is nothing more boring than a sailboat regatta, particularly one held outside a midwestern city in July.

  But I had an alternative plan, a plan made possible by the demise of the Stinker only the week before. In its place was a brand-new Jeep Cherokee with a trailer hitch.

  “Melissa,” I said.

  “Yes?” She glanced at me as we took the turn past a monument marking the birthplace of Abiah Folger, Benjamin Franklin’s mother.

  “How about the four of us sail in the Connecticut River Race?”

  I had expected an incredulous laugh. Instead she said, “When is it?”

  “Sometime in early June.”

  “What is it, exactly?”

  “A two-day trip from Hartford to Essex, Connecticut. Two people per Sunfish. You camp overnight, so you’ve got to bring all your gear. My impression is that it’s more of a voyage than it is a race.”

  “Where’d we get the second boat?”

  “Sam says we can have his.”

  “How’d we get there?”

  “We’d put both boats on the Beetle Cat trailer.”

  Melissa looked over her shoulder at the kids. So far her face had betrayed no emotion. By this point we were at the stop sign near the old Quaker Graveyard, a stoneless, rolling field of closely cropped grass.

  “Jennie, Ethan, what do you think?”

  Since they hadn’t been listening very closely, we had to reintroduce the proposal. When Ethan heard there was camping involved he was all for it. Jennie wasn’t as enthusiastic but seemed amenable.

  We pulled into the parking space beside our house and sat in the car talking. All sorts of logistical problems had to be worked out, but none of them seemed insurmountable. At last Melissa nodded and said, “Let’s do it.”

  Pre-Cut

  IN THE SPRING I became something of a media darling, appearing in not only the local newspaper but also Nantucket Magazine. Early spring is a very slow news time on Nantucket. In fact, March is known on the island as “Hate Month.” After a long winter of being cooped up, people start trading vicious rumors, and by the beginning of spring, the island is a tiny cauldron of scandal and suspicion. Any news—even a story about some guy sailing his way through a midlife crisis—is welcome news if it occurs in March. So after meeting a writer and a photographer on the shores of Miacomet Pond, I performed pirouettes out on the water and answered their questions. What had been a relatively secret quest was about to become public knowledge.

  Since the island is surrounded by the cold ocean, spring is slow in coming to Nantucket. It wasn’t until the first weekend in May, when I returned to Miacomet, that it felt as if winter was dead and gone and summer might not be too far away. People were fishing along the pond’s banks; an assortment of canoes and tin fishing boats had fanned out across Miacomet’s long and narr
ow confines. I was no longer alone.

  After a half hour of mark-rounding drills in the southern extremity of the pond, which was so close to the ocean that I could hear the steady roar of waves, I decided to sail the pond’s entire length, a dead beat that would provide excellent tacking practice. Soon I was tacking on an almost continual basis as the pond burrowed its way into a section of trees and marsh grass. It was like sailing in the midst of a forest. Ahead I could see three boys fishing. They seemed somewhat perplexed to see a sailboat coming their way. The youngest one shouted out, “Is sailing fun?”

  “You bet,” I said breathlessly. All the tacking was wearing me out. “But you know,” I continued, “I think I’m about to run out of room.”

  Soon after I sailed past the boys’ fishing lines, the pond petered out into a swampy section of marsh grass. The pond was too narrow, less than six feet, for me to turn around.

  The boys and I talked for a while. They were fishing for perch but hadn’t caught anything yet.

  “Know what I’m going to do?” I said.

  “No, what?”

  “I’m going to sail out of here backwards.”

  “You can do that?”

  “We’ll see, but first you guys better pull in your lines so I don’t run over them.”

  Sunfish are easy boats to sail backward. The trick is to hold the boom to the windward side so that the sail fills in from behind. With the rudder now at the front of the boat, steering is not only reversed but exceedingly sensitive.

  Soon I was picking up speed in reverse, zooming past the kids in a kind of backward free fall. Given the narrowness of the pond, it felt almost like tumbling down an elevator shaft. Each little jerk of the tiller threatened to send me veering off into the pond bank, but I was able to keep the boat in the channel—a wild joyride in reverse that made me shout with excitement once the pond was wide enough to let me spin around and proceed in a forward direction down the pond. I turned and waved good-bye to the boys.