Nathaniel Philbrick. Second Wind. New York: Penguin, 1999. Print.

Nathaniel Philbrick is best known for his history books, notably Bunker Hill and Mayflower. The former is reviewed on these pages, the latter is on my “some day I have to read that” list. Second Wind is different. It is a personal account of the year he took up sailboat racing to fend off a midlife crisis.

Philbrick had been a nationally ranked Sunfish sailor in his youth and young adulthood. He competed on his college sailing team. He ended up living on Nantucket, the island twenty-four miles into the Atlantic Ocean off the Massachusetts coast.

As any reader of The Preppy Handbook will tell you, islands tend to be exclusive. When people from Boston speak of a Nantucket dollar, they are referring to a hundred dollar bill. At one time the island was famous for whaling and the China trade. There are still families on the island who trace their ancestry back to those times. However, today it is largely associated with the upper classes.

Philbrick tells us that when this story begins in 1992 he had been living on the island for about twenty years. Surprisingly, even though he and his wife met sailing, he had done very little sailing since he had lived there. Now in his forties, he decides to fix up his long-abandoned Sunfish sailboat and take up the sport again.

The Sunfish is a very small craft, not much more than a surfboard with a sail, but it has a following and there are numerous Sunfish regattas or races. Since Philbrick was a racer twenty-odd years before, he not only begins sailing again but looking for races to compete in.

Since his wife used to sail as well, this becomes a family hobby with his wife, his best friend, and his pre-teen son and daughter. Philbrick tells a story well, and this is not only a tale of family dynamics but one about a subculture most Americans are not aware of, the same way Confederates in the Attic tells a lot about Civil War re-enactors or The Big Year tells about birders.

This reviewer could relate somewhat to the book. Many years ago I went on a Scout camping trip to Nantucket, so I have been there. Being Coast Guard veteran, I became somewhat familiar with “ragboat” sailors and their regattas, though in the Coast Guard we always used motorized vessels (a.k.a. “stinkpots”). Philbrick does a good job of introducing the Sunfish and its sailors to us.

He has a few close calls as he sails in and around his home island. A few times he ignores some good advice and has to learn things the hard way. Sailing is not that much different from other life pursuits.

I once read a diary in which the writer recorded notes about books he had read. He did not care much for Two Years Before the Mast (another book on my aforementioned list). He wrote:

Finished Two Years Before the Mast by Richard Henry Dana – to my mind a very dull book, entirely too full of foreboom, royal spinnakers, and top gallant yardarm try sails.

Second Wind is a little like that. Although Philbrick does explain things pretty well, it helps if the reader has some nautical background or is not afraid of using a dictionary. Even with my experience as a Coastie, I had to look up one word. The map of Nantucket in the book was especially helpful in visualizing some of his sailing escapades.

In less than a year after he takes up the Sailfish again, Philbrick is sailing in regattas. One especially rugged one—because of the bad weather—takes place on the Connecticut River. He competes in national races in Florida and Ohio.

Because he had sailed competitively two decades prior to this, he renews some old acquaintances with people who are still racing. Second Wind is also a tale of family bonding. A prologue written in 2017 tells us that his son travels widely in a sailboat and his daughter became a Laser-class sailor. The family that sails together prevails together…

I do have one slight quibble. Philbrick identifies Hartford as Connecticut’s largest city. It is not. While it is the state capital, at the time of the story it was the state’s third largest city. Now it is the fourth. For well over a century the state’s most populous city has been Bridgeport. The part of the state closest to New York City is for better or worse its population center. The notorious Munson-Nixon Line goes right through the state. To the south and west of it are mostly Yankee fans, to the north and east of it are mainly Red Sox fans.