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A Thoreau Approach to Sailing


I know someone who spent two years, two months and two days staring at the water, living in a space 150ft square, and paying keen attention to the weather. This sounds like a happy circumnavigation, and in a sense, it was, because the person I’m referring to is Henry David Thoreau, whose book Walden was very much about a trip across new horizons while living close to nature. In his own words: “I have, as it were, my own sun and moon and stars, and a little world all to myself.” Walden’s subtitle is “Life in the Woods,” but it could just as easily have been “Independent Passage” or “Wind, Weather and Self.”

Another quote: “I could watch the motions of a sail forever, they are so rich and full of meaning.” That’s not Liz Clark or Dennis Conner. It’s our own Henry David Thoreau, and it’s why we can celebrate Thoreau as a model for sailors who love the water, adopt simplicity and advocate for nature.

Thoreau says get out and go, and I hear his admonition when my life’s other voices warn me to work instead of sail, urge another year’s caution before a passage or disapprove of my boat as too simple a craft. Thoreau can be any hesitant sailor’s encouraging companion.


It is true that Thoreau is sometimes dismissed as a moralizing scold—a cross between Fox News’s caricature of Al Gore and Saturday Night Live’s Church Lady. But there’s much more to this story. Thoreau is actually a cheerful champion of outdoor adventure and a supportive voice for your sailing dreams. Look, when he was just 22 he built himself a boat and launched it on a summer’s trip through New England. Sounds like good crew to me! Thoreau’s adventures were never smug lectures on the world’s wrongs, but celebrations of the possibility that, you’ll be glad to hear, included boats. His 1839 trip became A Week on the Concord and Merrimack Rivers, where he writes: “If rightly made, a boat would be a sort of amphibious animal, a creature of two elements, related by one half its structure to some swift and shapely fish, and by the other to some strong-winged and graceful bird.”

What sailor has not meditated on just these proportions from the deck of a surging racer or the cockpit of a steady cruiser? My point is that in Thoreau we sailors find a kindred spirit with ideals that can take us to sea.

Sailing away means untying from the dock, and Thoreau’s Walden urges just that radical measure. It’s a fact that Thoreau lived at Walden Pond in Concord, Massachusetts, between July 1845 and September 1847. It’s also true that he built with his own hands a cabin there, and that his cabin stood 10-by-15ft with about as much living space as your family cruiser.

At a total cost of $28, Thoreau’s craft cost less than a decent shackle will set you back today. This question of cost matters because Walden is dedicated to convincing readers that chasing their dreams costs less than chasing bonuses: “Most of the luxuries, and many of the so-called comforts of life, are not only not indispensable, but positive hindrances.” From this perspective, money burned upgrading the watermaker or electrifying the winches would be better spent sailing the sea. “Economy,” according to Thoreau, is the balance of freedom and cost. Of course, if you have the money to spend, old Henry would say spend away, but “Economy” tells me not to wait for a full purse later when I have energy and health now.

Life on the pond for two years, two months and two days was also a rebellion against the economy of 19th-century America. Ever disruptive, Thoreau opted out of consumer culture: “A man is rich in proportion to the number of things he can afford to let alone,” is another way of saying you can’t buy happiness. My wife, Whitney, and I sail a Beneteau First 42 named Nellie built back in 1983. Maybe we could have set aside more money over more years to buy a newer boat some later day… but we wanted to be on the ocean right away, and so we spent what we had.

In a sense, that cockpit and saloon are Walden Pond to us, because it’s there we transact our business in direct relation to the natural world. You’ll probably recall Thoreau saying, “I went to the woods because I wished to live deliberately, to front only the essential facts of life, and see if I could not learn what it had to teach.” There’s the gift sailing gives us—a direct encounter with the “essential facts of life” spraying across the deck in a Gulf Stream squall or waking us to an osprey’s cry. These intervals of practical engagement with the natural world are heightened by the simplicity that sailing spotlights and sailors embrace.

Like other favorite shipmates, Thoreau has a lively sense of humor. His books are full with giddy wisecracks: “Any fool can make a rule, and every fool will mind it,” or “It is not enough to be busy. So are the ants. The question is, what are we busy about?”

He charms with self-deprecation too, explaining that thanks to reclaiming nearly the whole printing of his own remaindered first book, “I have now a library of nearly 900 volumes, over 700 of which I wrote myself.” Another welcome quality aboard is that Thoreau was handy. He was a capable carpenter, building his own house and, as I said, building his own boat. Thoreau was a diligent worker, contrary to his loafing, tree-hugger caricature. He loved to tinker and fix, and even engineered a better lead for his family’s pencil business.

That said, his high moral purpose might make shipboard life tricky—he quit his teaching job because he disapproved of corporal punishment, famously got tossed into jail for refusing to pay his taxes, kept a vegetarian diet, was a fervent abolitionist and believed individual ethics must supersede social expectations. We keep it veggie aboard Nellie and oppose slavery too, but on last July’s Bermuda to Newport run I had to forbid politics as a subject aboard, precisely because a firebrand like Thoreau kept inflaming the watches. So if I’m looking for crew, someone practical, diligent and informed is always a good choice. Poor Thoreau, it’s worth noting, lived a short life of only 45 years, and his intimation that he would not live long led him to an intensity bright as any lighthouse.

Another way Thoreau inspires me to sea is his emphasis on direct experience. Thoreau’s deliberate encounter with the best parts of life happens by cutting through the various screens that separate culture from nature. In other words, feel the wind, tide and fog as tutors. “Simplify! Simplify!” is a strategy for learning directly from nature. “Every morning was a cheerful invitation to make my life of equal simplicity, and I may say innocence, with Nature herself,” Thoreau writes. This informative simplicity is an invitation modern sailors experience every time they let the wind propel them across the bay.

Aboard Nellie, Whitney and I have adopted a model of minimalism that both reduces our costs and makes the boat easy to run. For example, our tender is a Dyer Midget with oars. This little craft gets us quietly to the dock, tows sweetly and weighs but 80lb. It’s true we lack the speed of an outboard engine or the girth of a burly RIB, but there’s no gasoline to store, no spark plugs to foul, no engine to winterize…you know the list. There are trade-offs for sure—a squally evening means we stay aboard, three is the Dyer’s capacity for trips to shore—still we follow Walden to simplicity.

Another example of our simplicity aboard Nellie is that we like our icebox. Many people love their onboard refrigerators, and I’m glad for them. For me, though, the cold plate demands more charging, the intermittent freeze/thaw demands more attention, and the upgrade demands more money. Thoreau would say it’s better to buy a bag of ice when you can, eat simple meals in beautiful places and get out on the water now.

This call to inexpensive action also the focus of the excellent book Sensible Cruising: The Thoreau Approach by Don Casey and Lew Hacker (1986), in which the authors argue that prospective cruisers should simplify their boats and cast off before it’s too late. “My greatest skill has been to want but little,” says Thoreau, and Casey and Hacker follow his lead, thereby showing sailors they have fewer needs and more wealth than they think. Sensible Cruising counsels us to go sailing now.

Thoreau's cabin

Thoreau's cabin

Yet another profound connection between Thoreau and sailors is nature and, in particular, the romantic confidence that time in nature aligns us with our best selves. Of course, my nature appreciation may dim when mosquitoes devour my neck at anchor or when tide fights wind off my bow. However, it’s also as clear as rum follows sunset that sailing puts us all in direct contact with the currents and the clouds and the creatures of the sea. Like his Transcendentalist comrades, Thoreau thought of nature as a gateway to the fullest self. For the Transcendentalists, nature was their Bible, their confessor and their temple. “My purpose in going to Walden Pond was …to transact some private business with the fewest obstacles,” explains Thoreau. Moving to the woods and building your own cabin (or buying that Valiant 40 and sailing to Antigua) floats you on the current of your own inherent divinity.

Thoreau says all this self-improvement and nature loving needs more than a walk in the park, that the most transformative Transcendentalist insights only come through wild nature because wildness enforces self-reliance like gales enforce storm sails. Whether you race Optimists, cruise to Fiji or daysail from a trailer, the heart of the whole soggy enterprise is making your own way, under your own power, using your wits. That’s self-reliance. Troubleshooting a sticky winch aboard Nellie, getting that genoa to fly a little fuller connects me to the logic that brought Thoreau to nature because it puts me in direct contact with the environment and with my own capacity to shape my condition.

To sum up, for sailors there’s more to sailing than rounding marks and plotting courses, the same as Walden was more than just a place to sleep for Henry David Thoreau. At the end of his life Thoreau warned, “In wildness is the preservation of the world.” To me this cuts two ways for sailors: on the one hand, our time amidst right whales, shearwaters and rain squalls brings out our best selves; on the other, sailors are witness to the polluting, over-fishing and acidification afflicting the planet’s wildest watery realms. Thoreau was an outspoken firebrand throughout his short life, and we too can speak for the coral reefs and marine species we know directly. Even when Walden Pond looks too shallow for sailing, I remind myself that Thoreauvian qualities like economy, self-reliance and attention to nature inspire great days afloat nonetheless. 

October 2018



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