I remember one morning, a few years ago, when I felt as happy and free as I ever have. It was early May, I was alone in the Hebrides, and had launched my small wooden boat into the quiet waters of a loch on the east coast of Harris. The boat itself was a perfect thing, sixteen feet long, wide in the beam, with a hull made of larch boards on an oak frame. It had a single dipping lugsail whose ocher fabric, when the wind filled it, stretched from the bow almost to the stern in one long sickle-curve above me. I could sit there, one hand on the tiller, the other on the mainsheet, and watch this beautiful form driving the boat onward as if by hidden magic.

Out of the loch, a light breeze came in over my left shoulder. I had about fifteen miles of sea to cross, but the boat cut its way easily through the mildly rippled surface of the Minch. The sea was sparkling in the sunshine, and I had to squeeze my eyes against the little shafts of sun coming off each wave. A pair of pale, scarred Risso’s dolphins swept past me, curving up and down together, breathing as they rose. A long black minke whale slid through, as dark as the sea itself, easing away to the south. Above it, kittiwakes and a great skua flickered and turned across the perfect seascape.

Long swells were creaming in from the north, each a hundred yards from crest to crest and about eight feet high. At one point they rose over a hidden rock ridge into a band of surf half a mile long. In the sunshine it looked Hawaiian, a gleaming white brow of breaking sea. I kept to the south of it, and pushed on and across the sea as if it were a kind of downland on the move. The tide was carrying us with it, running at the flood, as much as three knots in places, bubbling occasionally into flat mushrooms of upwelling water where the submarine topography had disturbed the flow.

It was a morning of ecstatic ease. The sea and wind were sliding me to my destination and the long-limbed stirring of the boat for these three or four incomparable hours on the wide Atlantic became for me the model of life in an accommodating world.

The beauties of sailing, particularly in a small boat, are dependent on that kind of mobility and fluidity. Nothing is fixed. The boat moves; the helmsman moves within the boat; the sea and wind move; the sail, sheets, and rudder all move. Their arrangement is only coherent at each particular moment. A setup that works for a minute or two will not continue to work as the wind shifts and the sea changes. Fluidity is all, and it may be that the sense of wholeness that comes with sailing when it is as perfect as this is a product of that sequence of temporary and transient solutions. It feels like flight, or like the dream of Icarus.

A paradox is in play. Nothing could be less free than sailing out to sea in a small boat. You are subject to all kinds of disciplines. The sea itself is unreliable. You are never quite sure that your rig and hull are all they should be, nor that you are up to coping with the uncertainties the process will throw at you. It is as dangerous as rock climbing. And yet, out of that cage of uncertainty, if you manage at the helm to find the right solutions and have learned to know the realities by which you are surrounded, a sensation emerges of unparalleled freedom.

I am not entirely sure why this should be. An unstable boat with a flighty rig is not where the culture has most often looked for certainty or comfort. The contemporary German philosopher Peter Sloterdijk has pointed to the fact that most Western philosophy has turned to the solidity of the earth as a place in which to understand and feel good about life. Philosophers, he says, have elaborated a “general world soil” as part of an overall “terranism” on which to base their thinking. Western thought has been on a long campaign to establish “foundations” for what it does. No thought can be valid without some meaty “groundwork” having been laid. “Grounds” are where truth is thought to begin.

But maybe the philosophers have been wrong about this? What if, Sloterdijk asks, we substituted “marinism” for “terranism?” If we all became marinists, the search for “bedrock concepts” would be over. No one would be interested in ultimate destinies. Movement and the voyage would become the thing. To leave would be as good as to arrive. We would stay mobile.

“Imagine a philosophy department attuned to the sea,” Brian O’Keeffe, a Barnard College philosopher, has suggested, ruminating on Sloterdijk’s idea. It would have constituted itself “as a swimming faculty, or at least as the port authority of Old Europe.” The philosophy department as the department for maritime affairs; philosophers as harbormasters and ship chandlers; Kant and Hegel in bathing trunks. If one envisaged a “nautical reformulation of philosophy,” Nietzsche’s Gay Science would presumably be the key text on the philosophical syllabus. “Send your ships into uncharted seas!” he exclaims. “Get on the ships! … The moral earth, too, is round! The moral earth, too, has its antipodes! … On to the ships, you philosophers!”

It would be a return to origins. Western philosophy began in the liquid. The sixth and seventh century BC thinkers in Miletus, the great trading and harbor city of Ionia on the eastern shores of the Aegean, all thought the ultimate reality lay in fluidity. For Thales, the underlying frame of existence was in water. For Anaximander, the ur-substance, the stuff from which everything comes, was the apeiron. The word means the “without-limit”: what exists before anything that we know and perceive in the world comes into being, the limitless and everlasting reservoir of being, the imagined state of liquid calm, from which everything that is emerges and to which all eventually returns. For Anaximenes, the third of these Milesian thinkers, the first material was neither Thales’ water nor Anaximander’s apeiron but the air itself, which through variations in its density gave rise to all other materials. “For all things come-to-be from it and into it they are again dissolved.”

Sailing on the sea in a small boat is a form not of escape but of submission to those primeval qualities, to the liquidity of things. It is the water equivalent of going for a walk, with nothing between you and the world as it is. Smallness is important because with the shrinking of the boat comes an expansion of the world. Crossing a stretch of sea that is only ten or fifteen miles wide, or finding one’s way down between the islands of a broken archipelago, carefully catching the tide gates as they open, or waiting at anchor for the tide to turn, becomes as much of an adventure as sailing from one ocean shore to another in a boat fitted to the scale of a wider sea. A small boat, in other words, is more like the clothes you wear than a vehicle you inhabit. You have shrugged off “the earth, earthy” – Saint Paul’s description of the first Adam – as something that stultifies and rigidifies and instead find yourself afloat in a kind of liberty.

This form of engagement with the actual is different from what people have often described as “the maritime sublime,” that sense of excitement at the scale of the sea, its open-endedness, the restraintlessness of being out and away from land. I have never been convinced by it. Conditions at sea are surely less free than those prevailing in a meadow or wood. The land is not cruel in the way the sea can always be. The sea, in many ways, is a tyranny. There is no freedom in the ocean itself. Its only freedom is in the boat and your relationship to it.

Any kind of seamanship that I have learned – and I wouldn’t claim much – does at least teach that almost everything that matters happens before you leave. Every sheet and halyard, every reefing line, every shackle, gudgeon, and pintle, every bit of clothing to keep you warm and dry must be in as good a state as you can make it. Every flake of acquired understanding has to be in play – what the wind and tide will do, where you can run to if things turn rough, where you can stow food and drink so that it is at hand without leaving the helm. Only then can you set off. Homer knew all about the beauty and holiness of preparation for what he calls “the salt desert of the sea.” For the great Greek epics, the readying of a ship was a form of liturgy. Every voyage described in Homer begins with that making good of the little wooden world on which the heroes would rely.

This is the paradox: the freedom experienced by the sailor is dependent on observing the disciplines the boat requires. It is a question of trust, knowing that the boat’s hull and spars are good while knowing not to overload them in a wind. Knowing not to overreach but to treat the boat kindly and look for safety in the hope that the boat will treat you kindly in return. Being attentive to sea and wind, looking to be slow and careful in every move you make, every trimming of the sails, every tweak on the rudder.

It is the freedom of submission – but what sort of freedom is that? It steps beyond Isaiah Berlin’s famous distinction between negative freedom, which is the freedom to do what you feel like doing, whatever the consequences, and positive freedom, the sense of freedom that comes from fulfilling the best of your self, or even your true self. It is more like the idea expressed by the Canadian philosopher Charles Taylor, which he has called “situated freedom” and which sees “free activity as grounded in the acceptance of our defining situation. The struggle to be free … is powered by an affirmation of this defining situation as ours.”

This is a dense formulation, filled with paradox, but one that nevertheless understands that freedom is a form of acceptance of the limitations of the circumstances into which we have been thrown. It is not an assertion of the self against those circumstances (whether positively or negatively expressed), but an identification of the self with them. The only freedom can come from recognizing the limits of where and what you are. The small sailing boat in a wide sea makes that acceptance particularly easy. When lying on a sofa or having lunch in a restaurant, nothing seems more obvious than our ability to choose. The menu of life encourages the illusion of potency and feeds the arrogance that comes in its wake. The boat is the opposite of that. It imposes a necessary modesty, a submission to the all too obvious reality of the defining situation around you. You can only do what the boat requires you to do. And in that compulsion, mysteriously, a sense of freedom flowers, one in which your life is momentarily liberated from the need to choose, perhaps even from the need to be or proclaim a self.

No sailing vessels in the Western tradition have been more potent instruments of freedom than the ships belonging to the Phaeacians in the Odyssey. When Odysseus is finally cast up on their shore, wrecked by a vicious Poseidon and scarcely alive, he finds himself in the land of master sailors. They look down on him as an amateur and a vagabond, part pirate, part merchant, part failure. Their own fleet is a dream of perfection. So total is their command, so entirely do they give themselves to the practice of sailing, that the ships seem to sail themselves. The hulls seem to know the headings of distant harbors and the ships fly them there at speeds unknown to other nations.

Even in Iron Age Greece, attention to the realities of the ship and its methods can deliver a kind of freedom. When Odysseus is to be taken home to Ithaca, his departure from Scheria, the land of the Phaeacians, is a ritual of liberation. The king’s herald “shows him the way to the fast ship and the sand of the seashore.” The queen instructs her maids to provide him with a chest of clothes, a clean and washed mantle, bread, and red wine. When they come to the ship, the men

Spread a rug for Odysseus, and a linen sheet, out on deck,
Laid at the stern of the ship, so that he might sleep there
Undisturbed, and he went aboard and lay down in silence.

The crew gathers, sits on the benches, and with their oars start to take the ship out of harbor. As its hull begins to meet the swell of the sea,

Sweet sleep fell upon Odysseus’ eyes, the deepest
And sweetest of sleeps, and like death in its quietness.

In the most perfect of ships, Odysseus finds himself liberated from the pains of life.

As the stern lifted on the swell, the dark wave of her wake
Foamed behind her, and she ran on safe and sure.
Not even the circling hawk, the swiftest of winged birds,
Could keep up with her, as she carried a man
Equal to the gods in wisdom, one who in time past
Had endured much and suffered many griefs at heart:
The wars of men and the harrowing waters.
Now on board, he slept in peace,
Forgetful of all that he had suffered.