I still refer to 1992–93 as the “Second Wind Year,” the year I launched a comeback as a sailboat racer and taught myself how to write history. I was 36. I’d spent most of the previous decade at home with our two children Jennie and Ethan (then 9 and 6, respectively) while their mother Melissa supported us as a lawyer. Six years earlier we’d moved to Nantucket, and I’d become fascinated with the island’s past. A freelance sailing journalist and former English major, I’d managed to write a handful of articles about Nantucket’s literary legacy but had hopes of some day delving much deeper into the history of my new island home.

Then, in the fall of 1992, I got my first big break when I signed a contract with a small local publisher to write a history of Nantucket. I had only a year to complete the manuscript, but since Ethan had just entered the first grade, I now had until 2:30 in the afternoon before the kids came home from school. It was an unheard of expanse of uninterrupted time compared to what I had known over the course of the last ten years. In fact, I was so giddy with the prospect of all the new-found freedom that I decided I must tackle one more, not-inconsiderable task. I must start to sail again. In college I’d been an All-American sailboat racer, and that fall I vowed to recapture some of my former glory by training for the Sunfish North Americans, the same championship I’d won 15 years earlier.

It proved to be a landmark year, during which I established many of the patterns that still govern my life. I still attack the writing of each book with a manic focus that has become all too familiar to Melissa. Twenty years ago, however, I was possessed by a level of energy and pent-up frustration that was, in retrospect, beyond even manic. Sane people do not sail a Sunfish around and around the perimeter of a tiny pond in over 30 knots of wind when the temperature is below freezing—and that was one of the tamer stunts I pulled that year of training for the North Americans.

Now in the fall of 2012, I am happy to report that Melissa and I still live on Nantucket. We also still sail a Beetlecat, one of the boats that appears in the following pages, although I’ve long since donated my Sunfish to Nantucket Community Sailing, an organization I helped found soon after the Second Wind Year. Jennie grew up to be a highly competitive Laser sailor and was a member of a nationally ranked sailing team in college. Ethan, never a serious racer, still loves to sail; in fact, a few years ago he and his husband Will sailed our 34-foot sloop Marie J around Cape Cod for their honeymoon. Soon after, Jennie’s husband-to-be Bryan was introduced to sailing aboard Marie J during an interminable six-hour race in a howling sou’wester. Perhaps not unexpectedly, Bryan and Jennie decided that a honeymoon spent climbing Mount Kilimanjaro was preferable to the questionable thrills of a wave-drenched sailboat. Marie J has since been replaced by the more comfortable centerboard yawl Phebe, named for an eighteenth-century Nantucket whaler. One of these years Melissa and I hope to sail her down the inland waterway to Florida.

I’ve written eight books since the publication of Second Wind in 1999, several of them about America’s relationship to the sea. This is the book with which I explored my own relationship to both salt and fresh water, and I hope you enjoy the voyage.

Author’s Note

I never thought I would have a midlife crisis. As far as I was concerned, all of life was a crisis. To point to a single event as the defining moment of one’s middle age was either a babyboomer’s self-dramatization or, at the very least, wishful thinking. Doesn’t the word “midlife” imply that you’ve got more than a few good years left?

I’ve now come to realize that the events described in this book, all of which occurred between the spring of 1992 and the fall of 1993, constituted, if not a crisis, a kind of watershed. Before that year, I was a stay-at-home dad who only got out of the house to take my two kids to the playground. While I considered myself lucky to be with my children every day, I had lost almost all touch with sailing, the sport that had once meant everything to me.
Then everything changed. For reasons I am still trying to understand, I decided to take another shot—maybe one last shot—at the Sunfish championship I’d won fifteen years before. I began an odyssey that led me from the lonely ponds of Nantucket Island to a humbling return to competition in Florida, then down the Connecticut River with my family before I headed out to a steamy lake in Illinois for the North American championship. In the end it brought me home, to Nantucket. That all this happened while I was working on a history of the island—a book that tells of a place experiencing its own midlife crisis—makes me scratch my ever-lengthening forehead and admit that, well, maybe its author was having one, too.
Since that weird and wonderful year, my children, who were not sure what they thought about the sport back in ‘93, are now better sailors than I ever was at their ages, competing in regattas on Nantucket and beyond. While I haven’t raced my Sunfish much in the last five years, I recently purchased my own Beetlecat. Now my wife and I can continue the rivalry referred to in Chapter One.

Any author incurs a great many debts when working on a book, and thanks for this project are long overdue. First, I’d like to express my appreciation to everyone who has ever raced a Sunfish. You created an atmosphere of competition and camaraderie second to none. Sunfish class historians Rapid and Donna Buttner were a huge help. Thanks also to the friends, especially Marc Wortman, Mark Poor, Wes Tiffney, and Bruce Perry, who provided essential encouragement during my year of pond sailing.

Without the interest and insight of John Burnham, Doug Logan, and Peter Gow, this book would have never been written; without the enthusiastic support of Mimi Beman, it might never have been published. Thanks also to Mimi Harrington, Nancy Thayer, Tom Congdon, Paul Odegaard, and Stuart Krichevsky for their input regarding the ever-evolving manuscript. Island artists Illya Kagan and David Lazarus generously lent their support to the project. Wally Exman, Walter Curley, Justine Klein, and Susan Klein at Parnassus Imprints were most helpful, as was Margaret Moore, curator at the Egan Institute of Maritime Studies. Special appreciation to Albert F. Egan, Jr. and Dorothy H. Egan, whose support through the Egan Foundation and the Egan Institute of Maritime Studies kept me afloat during the writing of this book. Finally, in addition to my wife, Melissa D. Philbrick, and our children, Jennie and Ethan, I’d like to thank the family that first put the wind in my sails—my parents, Thomas and Marianne Philbrick, and my brother Sam. Here’s to future voyages together.