Second Wind: A Nantucket Sailor's Odyssey

by Nathaniel Philbrick

  By the spring of 1992, I was working on a history of Nantucket that gave me a renewed appreciation for the island’s maritime traditions. And even before I’d made that America’s Cup–induced resolution to get back into serious racing, I found myself making another sailing-related commitment: I had agreed to run the sailing program at the Nantucket Yacht Club. I’d always assumed my days as a sailing instructor were behind me. But Jennie and Ethan were growing up, and as a seasonal position, the job dovetailed nicely with my life as a writer.

  That summer Melissa and the kids were given the opportunity to race a borrowed Beetle Cat (known as a Rainbow on Nantucket), the same kind of boat in which Melissa and I had had our first date. Although I was happy for them, it was also frustrating. As they won an impressive number of blue first-place flags, my yacht club duties required that I remain rooted to an NYC support boat. I felt left out of my children’s introduction to the sport that had been so important to my own coming of age. And what about me?

  As the summer passed, the conversation around the dinner table was becoming unendurable.

  Jennie: “How many flags have we won so far?”

  Ethan: “Four.”

  Jennie: “But they’re all blue.”

  Ethan: “I know. I’d like a red one.”

  Jennie: “Or how about a yellow one?”

  Ethan: “Mommy, can we come in third next weekend, please?”

  It was clearly time for someone to put my wife and especially my children in their place. By the end of July, I’d come up with Plan Gordon.

  Gordon was new to the sport. A marathon runner and bike racer, he had purchased a Beetle Cat only the year before. Although he was obviously in tip-top shape, he lacked the experience to race competitively and was becoming frustrated. He needed some tactical advice and instruction. What he needed, I decided, was me. One Saturday morning I happened to run into Gordon on the yacht club lawn. It was soon agreed that I would crew for him in the first race after I had assisted my staff in setting up the race course.

  Part of the beauty of Plan Gordon was the element of surprise. Melissa and the kids would have no idea what they were up against until the last possible moment. And, as luck would have it, they were over on the other side of the harbor when I jumped from the yacht club’s mark boat into Gordon’s Beetle Cat.

  With only a few minutes before the start, I fiddled with the various adjustments to the sail in an attempt to optimize its shape. As I stared up at the flapping panels of Dacron cloth and tugged on some lines, Gordon questioned me about what I was doing. Although I tried to answer as best I could, I found myself irresistibly looking out for the competition: a white Beetle Cat with a green sail and three members of my family on board.

  An air horn sounded, indicating that we had three minutes before the start. With a familiar rush of adrenaline, I reached involuntarily for the tiller, but there was Gordon—and he needed some pointers. I told Gordon to sail over toward the committee boat. That’s where Melissa and the kids were hanging out, their sail luffing lazily as Ethan dangled his hand in the blue, sun-glinting water. These guys wouldn’t know what hit them.

  On my cue Gordon tacked, turning us so that we crossed into the wind and ended up beside Melissa, our sail also luffing. The rest of the fleet of about five other boats was behind us, which was good—as long as we didn’t cross the line too early.

  “Hey, Daddy!” Jennie shouted. “What are you doing out here?”

  I chose to ignore her. I did notice, however, that her mother was looking straight at me. Melissa knew exactly what I was up to.

  We were down to the last thirty seconds, the most critical time, with that green-sailed Beetle beside us. Ethan, the collar of his yellow lifejacket pressed up against his chin, looked under the boat’s sail.

  “Hi, Daddy!” he called out.

  Once again, I chose to ignore him.

  “Daddy!”

  “What?” I finally said.

  “How ya doin’?”

  “I’m doing—”

  The starting horn blew, and in a blink of an eye Melissa and company were off. Okay, so I was a little late pulling in the sail, and maybe that’s why they were able to surge ahead of us, but if Ethan had just not distracted me . . .

  Since sails flutter uselessly like flags when pointed directly into the wind, a sailboat must approach the first “upwind” mark indirectly, tacking back and forth across the course. And where a Nantucket whaleman thought in terms of weather systems and continental currents as he navigated the oceans of the world, a modern small boat racer approaches each momentary change in the wind as if it were a storm front, each point of land as if it were Cape Horn. This hypersensitivity to the elements means that the first leg of a typical race becomes a panicky, zigzag quest for the fastest path to the windward mark.

  And as it so happened, halfway up the first leg we caught a nice wind shift on the right-hand side of the course and were suddenly back in contention. Gordon was doing an excellent job of steering the boat, and yet I found it impossible not to be a micromanager, offering a continual stream of advice: “Toward the sail a little bit . . . now away from the sail . . . that’s it!”

  The first mark of the race was a torpedo-shaped buoy anchored in the harbor channel, not far from the long barrier beach, known as Coatue, that forms the outer edge of Nantucket Harbor. Since the entire, seven-mile length of the harbor empties and fills around the end of this giant sand spit, the current there is usually quite fierce, as much as three to four knots. But all concern for the current was temporarily suspended when I realized that we were battling for first with Melissa and the kids.

  The conservative thing for us to do would have been to duck behind Melissa and then tack, essentially following her to the mark. But I was not about to yield. It was all or nothing. I told Gordon that with one perfectly executed tack we could knife in between Melissa and the mark. He looked underneath the sail to see what lay ahead. What he saw obviously worried him. “Are you sure?” he asked.

  But by then it was too late. “Tack!” I shouted. As Gordon jammed the tiller over, I realized that I had made a terrible mistake. The tide was rushing in much faster than I had realized. Try as I might to get us moving forward instead of sideways in the current, we were soon wrapped around the buoy.

  There is nothing worse than being pinned against a mark in a strong tide. It’s humiliating, particularly when your wife and children sail past singing “Found a Peanut.”

  There are no referees in sailing; it’s up to the competitors to discipline themselves. If you commit a foul, by hitting a mark or another boat or by getting in someone else’s way, you can exonerate yourself by sailing one or two complete circles (depending on the seriousness of the transgression) as a penalty. It is not a fun maneuver, and after disentangling ourselves from the mark and doing our penance, I apologized to Gordon. To his credit, he seemed completely unflustered by the incident. Who cared if we were now in third? We were still in the hunt, with plenty of race left to sail.

  The wind was now from behind, putting us on a broad reach to the next mark. It turned out that Gordon’s boat was fast on this point of sail, and we were able to round the next mark in second. Melissa and the kids were still quite a way out ahead.

  Then it happened. Suddenly, and for no apparent reason, that green-sailed Beetle turned around and headed right for us. I could see Jennie up on the bow, her long blond hair flowing back in the breeze as she pointed at something in the water while Ethan shouted excitedly from the cockpit. Then, just before we came abreast of them, Melissa spun the boat around, the sail swooping across dramatically as Jennie plunged her hand into the water. The kids began to cheer. What was going on?

  Waving a sodden baseball cap in the air, Jennie explained: “I dropped it overboard and Mommy went back to get it.”

  Melissa smiled and shrugged. I didn’t know what Gordon was th
inking, but this was more than I could stand. This was a race. To turn back for a stupid hat was unthinkable, particularly when you were in first place. The implication was clear: I can do almost anything and still win.

  The gloves were off.

  We rounded the last mark with Melissa less than a boat length ahead of us. With one, relatively short upwind leg before the finish, it was time to make things happen. So we tacked in an attempt to find a shift of wind that would help us. But Melissa wasn’t about to let us get away with it, tacking almost immediately to position her sail between ours and the wind. So we tacked again—as did, of course, Melissa. It was, in the parlance of the America’s Cup commentators on ESPN, a tacking duel to the death.

  Beetle Cats are too heavy to tolerate too much tacking, but we put our boats through their paces. Luckily, the boat in third was unable to take advantage of our infighting, and we were still neck and neck going into the finish. On board our boat, the tension was palpable: my hands trembled with excitement; Gordon’s eyes blazed with competitive fire.

  It was a replay of the first leg. Melissa was approaching the finish line on one tack; we were on the other. The plan, once again, was to suddenly tack just ahead of her, shoot up into the wind, and grab the victory. If it was close, I figured my boys on the committee boat would give us the nod, knowing that their jobs depended on it. I warned Gordon of the impending maneuver, and both of us were glancing toward that green-sailed menace when Gordon laughed. He laughed!

  “Will you look at that!” he cried.

  “What?” I shouted. “What?”

  “Look at your son!”

  I squinted through my salt-spattered sunglasses. Ethan was leaning against the combing of the cockpit, his head wobbling drunkenly with each bob of the boat. My God, the kid was asleep! Asleep? At a time like this? Didn’t he know he was in the midst of a tacking duel to the death?!

  That, I must admit, took the stuffing right out of us. Slam-dunking a mother and her sleeping babe is a difficult thing to do, even if you are the husband and father. By the time Gordon and I pulled ourselves together, it was too late. The moment to pounce had passed, and when we did eventually tack, Melissa walked right over us and took the gun. The worst part was that she and Jennie didn’t cheer; otherwise they might have disturbed Ethan.

  Up a Creek

  BEFORE I KNEW IT, Labor Day had come and gone and the kids were back in school. Time for me to leave the waterfront behind and become a writer again.

  But after two weeks researching old documents, I was thinking about sailing again. The Gordon debacle still stung, but I knew that there had to be more appropriate ways to work out a decade and a half’s worth of stifled sailing frustrations than taking on my wife and kids in a Beetle Cat. I knew that relief could only come in a Sunfish.

  By the end of September I’d learned that the 1993 Sunfish North Americans were to be sailed on a man-made lake in Springfield, Illinois, in July. Illinois? In July? Wasn’t it kind of ridiculous, venturing to the Land of Lincoln from the Island of Ahab?

  For me the site had one undeniable advantage, however. Lake Springfield was notorious for its light winds. Since I was no longer in the physical condition I’d been in fifteen years before, the lighter the wind, the better. But there was another consideration. By traveling to Lake Springfield I would be, in a sense, returning home.

  We had moved to Pittsburgh when I was in first grade, and one of my earliest and most vivid memories of the place is of a ride our family took up the Monongahela River in a motorboat. Having previously lived in Burlington, Vermont, we were all shocked and horrified by just how industrial the place was: steel mills, barges, tugs, and—everywhere we looked on that hot summer afternoon—catfish floating on the river’s surface, either dead or gasping for oxygen. Soon enough, though, we had replaced the motorboat with a small sailing dinghy and moved our boating from the river to a series of man-made lakes.

  For the next several years, my brother Sam and I had preferred to stay onshore, either fishing or collecting crayfish while our parents sailed back and forth across the lake, almost always within sight, occasionally waving and calling out to us. At some point Sam and I had asked for a sailing pram of our own, and then, a few years later, a Sunfish, and we raced every weekend on the new and relatively large lake at Moraine State Park, about an hour outside the city.

  Although I hadn’t been to Pittsburgh in over a decade, I still looked back fondly at that lake, a body of water so placid, so hemmed in by trees and houses that sailing was more like a walk in the park than a journey into the wilderness. At Moraine, I was free to explore every vagary of the wind with a spontaneity and abandon that the ocean, with its tides, waves, and fogs, rarely permitted. Now, after more than seven years on a tiny island at the edge of the sea, I could still feel the pull of a liquid speck in the heartland of America. Springfield would be just fine with me.

  But one question remained: How to prepare for a regatta on an inland mill pond when I lived on an offshore island with the highest average winds in New England?

  * * *

  ON a Sunday at the end of September I went for a sail, but not in a Sunfish. I was once again in the Beetle Cat, but this time with Melissa and the kids. This was to be our last sail together before we pulled the boat out for the season, and I wanted to make the most of it. Also at work was an indistinct need to somehow redeem myself after that summer’s catastrophe on the race course. My wife and children, however, were in no mood for a sail. According to them it was too cold, 55 degrees and breezy, and the three of them huddled together in the windward corner of the cockpit, complaining every time a droplet of spray flew in their direction.

  In the southwestern corner of Nantucket Harbor is an area known as the Creeks. It’s the ultimate tidal estuary, a meandering mile through a wide plain of beach grass. Earlier that summer I had explored the Creeks in a small Boston Whaler, and I had inevitably found myself wondering what it would be like to sail down this intimate country lane of an inlet, so unlike the waters surrounding Nantucket.

  As long as the tide was flowing out, I knew we couldn’t get into too much trouble. If the tide was coming in, however, we’d have our work cut out for us when it came time to escape from this marshy maze. Sailing against both the current and the wind on a river that was only fifteen feet wide would be next to impossible.

  So what was the tide doing? I glanced at a nearby dock. The pilings looked to be wet above the waterline, indicating, I assumed, that the tide was indeed going out. All systems were go.

  I kept my plan to myself as we sailed past a virtual forest of wintersticks, the white pieces of wood that take the place of mooring balls in the off-season. Up ahead were the sheds and Quonset huts that comprised a shipyard. Beyond it lay the Creeks.

  By now we were steaming along with the wind behind us on a run. Without the frequent tacking and spray in the face associated with beating against the wind, a run tends to be a much calmer, more laid-back point of sail. But we were in no position to relax. The shoreline was coming up fast and Melissa and the kids wanted to know what I had in mind. So I told them. They said it was a dumb idea; we didn’t have enough time if we were going to pull out the boat that afternoon as we had originally planned. I assured them that it was going to be just a short, casual side trip; that the current would help us zip out of there in no time.

  Meanwhile, we were running out of water, and I was having a difficult time finding the mouth of the creek. It blended in with the beach grass and was proving very tough to spot from a distance. The centerboard was already halfway up, and it was scraping on the sand. I ordered Melissa to raise it all the way. Although Melissa and I first met while teaching sailing, the honeymoon was over a long time ago. As she pulled up the centerboard, Melissa began to mutter mutinously.

  Just before I thought we were going to end up on the beach, I found the creek entrance. But why was the tide so low? Shouldn’t it be
higher if my calculations were correct? But there was no time to speculate. Hugging the right bank, we barely made it over a sandbar and then, WHOOOOOSH! we were on our way, running at a good clip down a very narrow and curvy waterway. The creek went right. With the centerboard up, the Beetle skidded around the corner, and we bumped up against the bank, our wake cresting on the shallows behind us. This was beginning to feel like a ride in Disney World. But what about the tide? No doubt about it, the tide was coming in.

  I knew we should turn back. But all of us got caught up in the speed of our journey as we whizzed along, our sail bellying out over the marsh grass. A snowy egret looked up, thought about flying away, but stayed and watched us pass, less than three feet away. Beneath us we saw, with an intense and startling clarity, a sunken motorboat. On and on we sailed, following this narrow, curving strand of water until we had been transported into a wide and wonderful no-man’s-land of cattails and waving grasses.

  As we approached a private dock with several boats tied to it, I realized that there wasn’t enough room for us to make it past without crashing into the creek bank. So, after putting the centerboard down as far as it would go, I shoved the tiller over. But instead of cutting across the current, we slid sideways into the muddy bank, pockmarked with fiddler crab holes. Melissa pulled out the paddle and, between pushing and paddling, forced our bow around so that we were pointed into the onrushing current. The breeze filled our sails and off we went, the water gurgling past.

  It sure felt like we were moving right along.