A Gentleman Never Sails Against the Wind

Whether the good Commodore was quoted correctly or whether the reference is entirely apocryphal, it remains damned good advice. Sailing against the wind is like trying to fly in the face of logic. It is unnatural, uncomfortable and unproductive. It is an activity best performed by those loutish types who compose the crews of racing boats. Sailing against the wind is showy and vulgar. If you have the good taste and the good breeding not to wear argyle sox with a tuxedo (or perhaps anytime) then why in the world would you want to sail against the wind.

It is of course quite possible to sail against the wind. In fact, your boat is perversely designed to accomplish just that direction, although with great strain to rigging and crew. In spite of the fact that most sailing is accomplished off the wind, designers still are judged by how close to the wind their latest hulls and rigging can cling, no matter with what discomfort..

I am convinced that most cruising sailors will lay a course into the wind only as a last resort, or to demonstrate their bravery to an attractively rounded crewperson. The last time I tried to sail into the wind was on a passage from Sri Lanka toward the Maldives at the wrong time of the year. I use the word 'toward' advisedly, since we never did complete that particular passage. After six days of beating the bejasus out of our boat, our patience and our love for our fellow man, I glanced back longingly in the direction of the harbor we had left days before and discovered, to my horror, that it was still in plain sight. After six days of accepting cold salt water in the face and bearing the abuse of body and spirit, I said to hell with it, declared that discretion was the better part of valour, turned tail and ran back to Sri Lanka. The sail back took six hours and was wonderful.

There is a special kind of rapture associated with sailing with the wind. Everything is soft, easy and lacking in threat. As you come off the wind it suddenly becomes your friend and the seas, which a moment before were trying to beat your brains out, now fawn with the desire to help you along. Your boat, which on any close point of sail is forced to strain and labor and to go in directions which seem unlikely, lopes gaily along. Hull and sails accept the urging, rather than the prodding, of a softer wind and a gentler sea. Is is not more sensible to be pushed than to be vectored.

The sailor feels warm, since the wind is now at his back and is diminished exactly by the speed of his progress with it. A wind at the back is always less ennervating than one blowing into ones face. Eyelids and facial muscles relax and grimaces of tension, born of the winds of affront, are gently massaged away by the zephyrs astern. You have made magic. You have tamed Borea. You have, in fact, taken the wind out of your sails.

And all at no cost, other than the slight bother that you may not be going precisely (or even approximately) toward your intended landfall. But what the Hell. You recall with pleasurable superiority the Commodore's edict and giggle at the transformation of wind to whisper and stumblebum (which was always your opinion of yourself) to gentleman.

But hold! Is it really all that easy. Are there no negatives? None? Is the physics of life which has taught you (the hard way) that payment is extracted for pleasure suddenly reversed, declared null and void?

Uh Uh! The Piper, which you had hoped to be Heidesick, still has to be paid. The physics has held, and you slowly discover, as the memory of the agony of beating into the wind fades from your mind, the price of the bargain you have made with the wind. If Faust had been a sailor the Devil would have offered a run downwind instead of eternal life.

Running (sailing downwind) has inherent in it three seeds of sudden misfortune, any one of which can lead to loss of life or boat or both. The threat is more acute because the action of running has the appearance of safety. The sailor is lulled, his awareness blunted, his defences down.

Here is a worst case scenario. You are coasting downwind in about 12 knots of wind. Since your forward speed is about 7 knots you seem to be flying through a dead calm. What can possible happen? Well how about this. The wind picks up from 12 to about 20 but to you it still is apparently only 13 knots caressing your back, still a gentle breeze. As the wind freshens, as it is wont to do, it backs a bit to starboard and the stronger breeze increases the roll, which sailboats love to do downwind. You now have 20 knots of dangerously disguised wind, your main boomed out to starboard and a wind direction that has moved, unsuspected, in that direction, toward your leach (the free swinging end of your main.) As your boat rolls a little more to port in response to the stronger breeze, the more starboard wind catches your main in an uncontrolled jibe, sweeps your deck clean of two or three crewpersons, snaps your mast, rips out your port shrouds and leaves you helpless, mastless, sailess in the water unable to get back to pick up the crew overboard, some of whom may very well have been killed by the boom or knocked senseless and drowned.

You try to start your engine and find that the various halyards, sheets and shrouds trailing about you in the sea have fouled your propellor and you now realize that the freshening breeze has turned into a dangerous squall. You are about to pay the piper. If you think this scenario is far fetched just ask any blue water sailor what his recurrent, most terrible nighmare is.

While an uncontrolled, and unsuspected jibe is the most dramatic threat of downwind sailing there is a threat more pervasive, as expensive and, ultimately, as dangerous to a boat far at sea.


For every point of sail save running, the chafe problem, the bane of babies and sailing ships, has been brought under control. In beating and in reaching a little attention to chafe will protect your precious sails and lines. In running, the wind and the designers, to the greedy applause of the sailmakers, conspire to destroy sails in an hour that are expected to last for years. And if you are far at sea (and there is nowhere else worth being) and if you have no spare main (and how many of us do) then the piper calls. . . . the piper calls.

The odd thing is that these disasters waiting to happen to you are easy to deal with. As terrible as are the consequences of chafe and lulling and the uncontrolled jibe, just so simple is it to avoid them.

Chafe happens mainly to your main. It can be plainly seen that the shrouds and the spreaders are the chief enemies of your sail fabric, both providing available hard surfaces upon which to rub. Since your staysail and jennys are forward of these devils, it is you main that you must seek to protect. It is astounding that so serious a problem with so obvious an answer is so seldom addressed.

To avoid chafe downwind, never, never, never sail with an unreefed main. Take two deep reefs and the head of your main comes down below your spreaders and comfortably aft of the shrouds. You lose remarkably little speed since sail area is less critical and less elastic a factor downwind than it is either beating or reaching. And, as a bonus, if you should jibe, the power and the speed of a boom with a reefed main is substantially reduced.

To avoid a jibe always, always, always secure a line from the end of your boom to a good heavy cleat at your bow. Such a line is called a preventer. It is designed to prevent you killing yourself. Next question.

To avoid being lulled. Well now, that is not so simple. The lulling happens because the following wind is diminished by the forward speed of the boat. Try weiring about a couple of times from a quiet run into the wind and sense, as you will with shock, the power that is hangiing over your shoulder. When running pay closest attention to any slightest change in either wind direction or velocity. It is the changes that kill. At sea, as in Life, an unaltered state is rarely dangerous, an altered state always is.

We humans (sailors are human too) are a forward looking specie. Our ears point forward, our eyes point forward and our noses hang out ahead of everything forever sniffing out what lies formost. And we are always getting killed, incredibly suprised, by a stab in the back. We never do learn that aftward lies our unprotected backsides. So when a wind comes from your rear, full of pillow talk and soft promises, you can be damned sure that you are about to receive a whack on the ass.

In describing his ideal woman, a libidinous artist yearned for one with three breasts, two in front and one in the back, "Marvelous to dance with!"

A downwind sailor needs 'one in the back' too. Something a bit more sensory than, if not so attractive as, a bosom.