The Zen of Trailer-Sailing

Trailer-sailors enjoy small sailboats. Some are open cockpit daysailers. Some are small live-aboard cabin cruisers. All are easy to rig, launch and retrieve—and fun to sail.

Every trailer-sailing family with a sailboat loves the idea that they can cruise their dreamboat to windward at 55mph in any direction they wish. Most of these boats can be stored in the family garage. Snowbound northern trailer-sailors can trail their boats to Florida to cruise in subtropical waters. Sailors on the West Coast can head south to the rugged shores of Baja California.

All that trailer-sailors need is an open road and water deep enough to float their boat. Their numbers are large. They enjoy sailing close to the water so they can hear the swishing sound as it flows by, be it on a river, a lake, a pond or an ocean. They like being able to reach over the side and feel the water on which they are floating.

These gypsies cruise swiftly to the water by highway or dirt road. On long overland trips their boat doubles as a comfortable camper when they make overnight stops. They climb aboard and sleep comfortably. It doesn’t get much easier than that.

In 1944, when I was 17, money earned on a paper route enabled me to purchase my first “big” sailboat, a used and very dirty 15ft 6in wooden Snipe, for the grand sum of $100. That boat was my first introduction to the Zen of sailing. None of us had heard of the word back then, but Zen it was, and exposure to it stimulated all my senses.

In the beginning, all of our families had vacation cottages around Spring Lake, Michigan. Everyone had boats of some kind. The two Failing boys, Bob and Fletch, had a heavy lapstrake lifeboat that we rigged to sail. Jerry Bricker had a Crescent. Another kid lucked into a Lightning. I had my Snipe. Our fleet was anchored just offshore, ready to sail at a moment’s notice all summer long. In the winter all the boats were stored upside down on sawhorses beside the lake. We could hardly wait for the spring thaw to melt the three feet of snow on top of them and unfreeze the lake.

We repaired, sanded, painted or varnished our wood hulls each spring. I’ll never forget the fresh smell of sanded mahogany or the aroma of the many coats of Spar Varnish I painstakingly applied to my boat’s amber-grained hull. Inside, I painted everything dark green. The deck, with its V-shaped splash rail, was bright yellow canvas over wood. She was a delight to the eye and a heart-thumper of a racer.

One-star-studded summer night, a sailing buddy and I sailed her far out into the lake, dropped anchor and reveled in the adventure of it. We hoisted a red railroad brakemen’s lantern to the top of the mast for an anchor light, then slept on the cockpit floor with the centerboard well between us, lying on our cloth-covered cork life preservers. The warm night, the aroma of the wooden boat, the view of that starry sky and the distant calls of the whippoorwills left a lasting impression that lives to this day.

When wooden boats gave way to fiberglass, I thought I would never enjoy sailing again. The new boats looked as sterile to me as a refrigerator. I saw not an ounce of character in any of them.

Nonetheless, I mellowed with the passage of time. Years later, married and living in northern Florida, I bought a used trailerable 10ft 13in Sunfish. To make sure I knew how to handle it, I practiced sailing it around in the face of approaching storms when the winds were strong and gusty.

After that came a 16ft Hobie Cat. I regularly sailed on northwest Florida’s Lake Seminole. Since the cat was all sails with little wetted surface it was a rocket. On a gusty day, flying a hull singlehanded, I flipped three times in succession. Each time the mast made a 360 degree revolution underwater before I discovered how to right it in the strong wind.

This boat taught me much about the wind and the water, and I began to appreciate its sizzling high-speed runs—especially when we sailed so hard through waves in the Gulf of Mexico that the water vaporized around us as we yelled with delight.

It was addicting. So was being able to slide our 16ft raft onto the beach, where we dropped its sail, threw a bright yellow nylon boom-tent over the spar, and slept comfortably on its trampoline deck. I lived off the sea this way for a week with a friend. We called it “roughing it easy.”

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