In the midsummer of 1998 three of us in our 50s set out on Long Island Sound to sail my father’s 32-foot Pearson Vanguard, the Wiki, from City Island to East Hampton, where we had a vacation home at Settlers Landing. My dad had died the previous December, and during the last year of his life with cancer the boat fell into slight disrepair.
He did most of the work on it himself. It was tricked out for club racing, but a couple of items were problematic. The running lights weren’t working because the wiring needed an overhaul. The diesel engine had transmission issues; it occasionally slipped out of gear. I remember calling my crew a week before our trip and cautioning them about possible problems. In truth, I was trying to chicken out and abort the cruise, but they reassured me we would be fine. We were all experienced sailors.
On Friday, in the late afternoon, we motored out to Eastchester Bay, the Throgs Neck Bridge off to the south. There wasn’t a puff of wind for several hours, well into the evening. We began motoring. Around 8:30 p.m., just as it was getting dark, it began blowing pretty hard and we were finally under sail. We hoped to get to Port Jefferson, a traditional North Shore stopping point.
Around midnight we saw a dozen boats heading toward us with their spinnakers flying. We had no lights, so that was sort of disconcerting. I was at the helm, maneuvering out of their way. They might have thought we were smugglers. We then realized that the around Long Island annual race was that weekend. We finally dropped anchor in Port Jeff Harbor at about 2 in the morning.
When we shoved off the next day, we were motoring out of the channel when the engine slipped out of gear and I couldn’t re-engage it. A ferry coming in from Connecticut was headed right at us, so we hurriedly raised sails just as we were getting some stern toots from the ferry’s captain. The rest of the trip was somewhat uneventful. We pulled into Three Mile Harbor on Sunday.
Shortly after that first voyage, my mother sold the Wiki.
We didn’t yet know it, but that was the first of many such trips on Long Island Sound.
The three of us forged a close friendship while we were in elementary school in the suburbs. Our dads, Sam, Ben, and Elliott, sailed together at Stuyvesant Yacht Club on City Island, something of a misnomer. I never thought the hundred or so cabin cruisers and sailboats were really “yachts.” It was a middle-class, working-class club founded in 1890 (but didn’t survive the 2012 Hurricane Sandy). Our fathers shared a love of being on the water in a brisk breeze. They taught us how to sail. In those days when we cruised they went below to the chart table to plot a course. Then we grabbed a pair of binoculars to navigate by locating buoys, the nuns and cans that tell you where you are and where you’re headed. Today, we’re spoiled. We have GPS in the cockpit.
The three of us have a lot in common, and we’ve fallen into an easy division of labor. We somehow know who’s getting the sails up, who’s going to crank a winch on a given tack, who’s going to offer relief at the helm. One of us likes to command the galley. We agree on the important things in life except for baseball fandom. One of us is a Mets guy, the other a die-hard Yankees rooter, the third is a Red Sox fan. (If you are waiting for the punchline, I’m sorry to disappoint you. There is no joke, but we’re always amused when we think about it.)
A couple of years after that first sail together, David bought a 32-foot Catalina out of a local boat show, and we continued the tradition, albeit on slightly shorter cruises, which was probably a good idea now that we’re septuagenarians. His boat is aptly named, Loco, which helps explain some of our less-than-thoughtful decisions out on the high seas. Every Memorial Day weekend, we head eastbound from Huntington Harbor, where David winters the boat, to his home on Shelter Island. We sail it back along the Connecticut shore on an October weekend at the end of the season. We’ve likely done 35 of these cruises to date.
David runs the nephrology department at one of New York City’s leading hospitals. He frequently fields phone calls from his kidney patients and issues commands to his hospital staff while at the helm. (When I mentioned to his wife, Lois, that he was a “semi-workaholic,” she replied, “What’s with the semi?”) Richard, who decamped from New York to Massachusetts some years ago (and defected from the Yankees to the Red Sox), has a master’s in social work and still works part time as a therapist in private practice. I wince when I’m directed to check the “retired” box on forms that ask for employment status.
Of course, we’ve had our share of rainy weather, no wind (along with prosaic miles of motoring), uncooperative currents, heavy seas, and thunderstorms. You get used to the fact that foul weather gear only goes so far in keeping you dry. I call it placebo gear. When the forecast is particularly nasty, well, we’ve made some bad decisions. Once David and I shoved off in six-foot seas. Richard was conveniently missing in action that trip. The guy at the gas pump told us we were absolutely nuts to be out in that weather. As the only boat visible for miles, a Coast Guard cutter came by to see if we were okay. When I missed a trip, Richard ran aground going into a harbor. A couple of seasons ago, David ran aground in the Mattituck Inlet. (I have successfully avoided such an embarrassment, but they both warn me that my day will come.)
Richard’s wife, Nancy, has asked, “What is it that you three talk about for all that time?” He replied, “Life, death, and the great in-between.” He added in an email, “We have shared our aches and pains, heartaches and heartbreaks, fears, doubts, and insecurities, as well as our joys, hopes, dreams, and the exquisite bliss that comes from being under sail together in a stiff breeze, with one mind: to exert our skills as best we can to harness nature to our desire and objective. And in the process, I believe, time and years dissolve, and we are able to recapture, for a moment or so, that exuberance of an earlier time, when we had trimmer bodies (at least I did) and no gray hair.” I thought that an apt summary.
He added, “Our friendship is a rare thing, and I trust it will continue until one or all of us is no longer physically capable of trimming a sheet or handling the wheel. And then, we will continue to sail together in our dreams.”
Doug Garr’s books include “Between Heaven and Earth: An Adventure in Free Fall.” He lives in Manhattan.