Watering basics are pretty straight-forward; it's a shame many beginners don't follow them.
Once you have 'real' plants going, the best way to water is the soak and dry method. Before watering, wait until the soil is absolutely, completely dry. If there is even a small amount of moisture in the container/soil, it is too soon to water. Once you get used to the weight of your containers when totally dry (by lifting them) you'll be able to get a good idea how close to needing water they are from that. For example, the top of the soil might look dry, the whole thing may 'seem' dry, but when you lift it, it is not as light as it you know it should be when totally dry. Obviously this means don't water yet.
When it does come time to water, add it until it comes out the drain holes in the bottom then stop. This ensures all of the soil is wet. Then, of course, wait until it drys TOTALLY before watering again. The problem most beginners have, is they add water when the container is not completely dry. If the soil never dries, the plant cannot get the oxygen it requires to thrive and maintain a healthy root system. For one thing, drying helps to create nooks and cavities that air can get through. This is vital for proper plant growth.
A couple things to remember: 1 - The container you use makes a big difference. If you use a container that is too big for the size of plant you have, it doesn't dry out fast enough and the roots are surrounded by water for too long. If you plant a small plant in a big pail for example, you will notice that it doesn't grow near as well as a small plant in the right sized container. 2 - Plants can recover from a dry spell; over-watering equals disaster. In other words, less is always more. Of course, as 'rocker' mentioned, if a plant starts wilting, that is a sure sign it's ready for a drink.
Wilting a little bit won't hurt it; it's a hell of a lot better than over-watering. Hope this helps.