Sailing is fun! Raise the sails and off you go, but in which direction?
You probably have a destination in mind and will want to go in that general direction. When this destination is downwind from your current position, it doesn't take as much planning to get the boat going in the proper direction. When the destination is upwind from your current position, the proper course may seem a bit of a mystery to onlooking power boats.
Sailboats can move in any direction for a long time, except dead upwind. To move a yacht towards an upwind destination, you must set a course for a few degrees to the left or to the right of dead upwind. This course is known as a tack, and the act of changing from left to right of the wind is tacking.
To move to windward, you will end up sailing to the left or to the right of the wind. This will present to you the characteristic image that power boaters think of when they think of sailboats: "I want to go dead ahead, so I'm going to sail to the left of it, and then to the right of it!" With time (lots of time) you will make your way towards your windward destination.
An important thing to remember when working to windward is that longer tacks are preferred over shorter tacks. Every time you tack, you will loose some distance as the boat slows and gets in its groove again. If you loose a few feet of forward distance, then minimizing the number of these episodes will be very advantageous! If there is not enough water to carry out a long tack, then you will have no choice but to complete various short tacks. If the body of water you are sailing in is wide enough, the longer the tack the better.
A very important point to remember when sailing towards a windward destination is that it is best to overshoot the target and fall back to it instead of choosing your tack so you will come directly to your target. If there is any disturbance in your journey, you will slip to leeward. If you are aiming directly for your target, you will now need to carry out two additional tacks to arrive at your destination. If you aim for a more windward target, you will have leeway to allow for leeward slip which will mean that any disturbance will allow you to still reach your target without any additional tacks. As you overshoot your target, you can then begin to fall off and come into your destination with much more comfort and predictability.
While the ideal is to tack up and arrive directly upon your destination, the reality is that the winds will change, current could pick up, or debris could cause you to alter course (crab pots in the Chesapeake are a common offender). If you are picking your course so that you are close hauled and can't sail anymore upwind, then you have no leeway if you encounter a disturbance. You will undershoot your target destination. The alternative is to select an upwind target, to which you sail close hauled while keeping the final destination a bit to leeward of the target. This will allow you wiggle room if you encounter a disturbance and slip to leeward. As you approach your destination, you can alter course for the destination and sail on more of a beam reach. This will afford you the flexibility to turn more to windward if the situation calls for it.
The variability in the wind can be seen in these charts where we were sailing to windward. You can see how we do not follow a perfect straight line because the wind would shift or change in intensity and direction, as well as the influence of the ebbing and flooding tides. This is why it is a good idea to (windward) overshoot your destination and afford yourself the leeway. If you cut it too close, you might have to add some extra tacks to make it to your destination which will make your journey take even longer.