How do I manually wind the watch enough without overwinding it?

Manual-wind watches normally give you feedback when they are sufficiently wound by offering resistance at the crown. Never attempt to wind more after you start to feel this resistance--you can severely damage the watch.

Automatic watches operate quite differently. Since they have the capability of winding themselves, they also need protection against overwinding. So all automatic watches are equipped with a gear that disengages when the spring is fully wound. The advantage is that it makes it impossible to overwind an automatic watch. The disadvantage is that you loose the feedback of when you have wound your automatic watch enough.

Generally, mechanical watches take somewhere in the range of 20 to 30 turns of the crown to wind them fully from being completely run down.