The story of this photograph
That's a 13-year-old me standing at the stern, trimming the mizzen staysail. This was at the inaugural Block Island Race Week, in 1965. The crew was my parents, their friends, the Seymours, my 14-year-old sister, Patsy, and me.
The boat is my father's Tartan 27, Red Pepper. My father's favorite feature of the boat was that the ice chest was accessible from on deck. My mother's favorite feature was that it was also accessible from below.
The photograph was made by either Morris or Stanley Rosenfeld aboard Foto. Morris, age 80 at the time, was still photographing, but his son, Stanley was in the process of taking over the business. No doubt they were both on board Foto.
My Early Sailing History
Sailing was Dad’s thing, so my siblings and I were all enrolled in sailing school at the earliest possible moment. In this sailing school f you didn’t own a boat you crewed, so Dad bought Patsy and me a boat. When Dad came home with the boat he proclaimed that it was to be called “High Hopes”, and that evening we all sat around singing the song, “High Hopes”. (“Oops, there goes another rubber tree plant!”) Prophetically, we never painted the name on the boat, because eventually the boat was appropriately renamed, “Oops”.
I don’t know how old I was when we got that boat, but I would guess around seven. Just as, if you did not have about you had to crew, if you did have a boat you had to skipper. My first time out was not a positive experience. One of the instructors was my “crew”, but he sailed the boat out from the dock into the harbor. He then let go the tiller, moved out of the way, and said, "Okay, your turn.” I was terrified. I said, “No!”
The instructor, an 18-year-old kid, adjusted a few things to put us on to a collision course with a 250 passenger ferry boat and said, “If you don’t want to run into the ferryboat, you’ll have to take the tiller.” As if to punctuate the sentence, at that moment the ferryboat sounded its horn, no doubt to alert us that it would not be able to get out of our way. I started crying, and I swatted the tiller just enough to alter our course out of harm’s way.
I have no recollection of ever skippering in sailing school.
My mother was responsible for my developing my confidence to skipper a boat. Our family had a Trident, which was a knockoff of the Sailfish (which was the predecessor of the Sunfish-- similar but without a cockpit; just a flat deck on top.) One summer our family rented a house on Shelter Island, New York, and Mom would take me out on the Trident. In time I handled the whole operation, from rigging and launching to skippering, docking, and unrigging, as long as she was there with me. My fear about going out alone was that I would not be able to get back again, but one day Mom convinced me to give it a try.
You can’t sail directly into the wind. If you want to go that way you have to zig-zag back and forth around 45-degrees from the wind, working your way up. This is called beating to windward. The goal when beating is to sail as close to the wind as you can while keeping the sails full of wind. If you point too close to the wind then the boat stops, and if you don’t point close enough to the wind then you don’t make much progress into it. This is what concerned me. I imagined myself sailing back and forth forever, never getting home again. Sailing perpendicular to the wind is called reaching. If you reach in one direction then turn around, you reach back to your starting point. No beating necessary. That was a comforting thought. When I acquiesced to Mom’s gentle encouragement to go it alone, I did so understanding exactly what direction I needed to go so that I could turn right around and come back. Reach out; reach back. That’s what I did. Back in forth, back and forth, back and forth. For the rest of our stay on Shelter Island.
In 1965, my parents, two of their friends, my older sister, Patsy, and I raced our family’s 27-foot boat, “Red Pepper”, in the inaugural Block Island Race Week. I remember the week fondly as long as I don’t remember too carefully. I spent several days throwing up over the leeward rail. I don’t know why some people are prone to seasickness and some are not. I’m the only one in my family who is. The morning routine aboard Red Pepper was to relax and read after breakfast until it was time to leave the harbor. After several days I discovered that if I did not read in the morning I was less likely to experience seasickness. That was a significant discovery.
At 13 years old, I had few responsibilities while racing, but Red Pepper was a yawl, with two masts, and the small mizzen sail on the after mast was my baby. I was also a pretty fair winch grinder. (At 14, Patsy was the navigator, and she was really good at it.)
The year I turned 15 I convinced my parents to release me from sailing school. That summer I had two different jobs. The first was to drive a 50 foot powerboat around Long Island Sound watching twelve-meter yachts run practice races in preparation for the America’s Cup.
That year four American boats were vying for the opportunity to defend the Cup against an Australian challenge. Those were Weatherly, Constellation, Columbia, and the brand-new and very radical Intrepid. During the month of June the crews honed their skills and tuned their boats in races on Long Island Sound, and I was hired to drive this boat while the boat’s owner, his wife, and their guests sat in the cockpit drinking martinis and watching the races.
One day I overheard the owner explaining to his guests about the great skill of the sailor on board one of the spectator boats. It appeared there was only one person on board this 27 foot sailboat, and he was sitting calmly on the foredeck while the boat sailed skipper-less on a steady course. I steered us nearer to that boat to give my passengers a better look at this obviously consummate sailor. When we were within hailing distance, the man on the foredeck waved and shouted, “Hi Son” I shouted back, “Hi, Dad!” The owner and guests looked up at me with new respect,
but, hey, even that 18-year-old sailing
instructor half my life earlier could make a boat sail itself. These folks didn’t know much about sailing. We went back to watching America’s Cup boats.
My second job that summer also involved driving a motorboat and watching sailboats. Our yacht club, in addition to a “junior sailing program” had a “ladies’ sailing program”, and that summer I drove the instructor around while she instructed the ladies. The best thing about that job was learning exactly where to position my boat to give the instructor the optimum view of the boat she was working with. From this position she (and I) could tell whether the sails were trimmed correctly and if not, what needed adjustment. I also learned to recognize when the sails were not tuned (i.e. shaped) correctly by looking from that angle. This turned out to be some of the most valuable sailing instruction I ever received.
I spent several years attending boarding schools, where the school year ends about a month earlier in the summer than public schools. During that month my siblings and friends were all in school during the week. By that time my family owned a Sailfish which I would sail to pass the time. As I’ve said a Sailfish is just a flat deck on top, so it’s great for lying down on. I would lie on my back with the tiller behind my head and sail a course where if I turned one direction the sail’s shadow would fall across my face, and if I turned the other direction I would hear the sail luffing (flapping like a flag). Holding the tiller behind my head, I’d close my eyes and just go. Needless to say, by this time I was confident I could get home.
In boarding school my fall activity was football and my winter activity was skiing, but I needed a spring activity. I’m not a baseball player, and lacrosse did not appeal to me. It turned out that the school had a sailing team, so that’s where I ended up. In ninth grade I was the crew on one of the three varsity boats. Ironically my skipper, Chip, was from my hometown and his family belonged to the same yacht club mine did. Like me, Chip did not attend sailing school in the summer, because he also wasn’t that into sailing. We were a good match. And we were the number two Varsity boat. I lettered in sailing. What a hoot!
After high school I attended music school in Boston for a year. I spent a lot of time bicycling, and one day as I was crossing the Charles River I saw a lot of activity at the MIT sailing dock, so I headed in that direction. I wandered down on the dock and (surprised not to be stopped by security) struck up a conversation with a guy who was just finishing rigging his boat. He asked if I would like to join him for a sail. I said sure. It turned out he was enrolled in a sailing course and was practicing. He had a test coming up in which he would need to know the names of all of the parts of the boat, sails, and rigging. I probably knew the terms ‘port’ and ‘starboard’ before I knew ‘left’ and ‘right’. The rest of the nautical jargon was also second nature, so I lay in the bow on a beautiful, warm, sunny afternoon, and quizzed this student on nautical nomenclature while he sailed. It was a delightful afternoon.
In my early 20s I was living at my parents’ house and studying photography. I bought myself a Laser. A Laser is a 14-foot high-performance, single-sailed boat that’s loads of fun to sail. Though I didn’t know it at the time, it was designed by a member of our local yacht club. The club seems to attract good sailors. When my father wanted to charter a boat in the Caribbean for my parents’ 25th wedding anniversary, he needed to supply references. He told me that two former America’s Cup skippers were Club members and would be happy to endorse him. Calling the club a ‘yacht club’ might be a little misleading. The clubhouse consisted of a locker room where you could store your sails, a small meeting room, the junior sailing program meeting room, a large room for folding sails (and for dances), and the snack bar. There was also a pier, docks, and a large area for storing boats, but that’s it. Nothing fancy. This club was all about sailing (and racing).
But back to the Laser: my friend Steve also had one, and we spent many days just screaming around Long Island Sound. But my most vivid recollection of the Laser is of a day when the wind was really blowing. Although the Laser is designed as a one-person boat, Steve, my girlfriend, Mary, and I all went out on my boat. The boat has a strap running lengthwise near the bottom of the cockpit which you put your feet under so that you can lean out the windward side without falling overboard. You do this to keep the boat from capsizing. All three of us had our butts over the rail and were leaning for all we were worth, and I still had to spill some wind from the sail to keep us upright. We were just flying. The slightest twitch on the tiller would carom the boat off in a new direction. It was one of those peak moments of exhilaration.
At this time, my brother, Rocky, was working on a serious ocean-racing yacht called ‘Gem’. He was the full-time employee whose job it was to keep the boat race-ready and get it to the site of the next regatta. That day we were out on the Laser he was taking Gem to her next destination and we came across him on the way. He was under power and we flew by him, planing to windward. Ok, that doesn’t mean anything to you non-sailors, but a rough translation might be: ridiculously fast.
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