It depends. If I brew an ale that is 1.055 or lower OG, I pitch a yeast I am familiar with, and the temps are where I want them to be, I'll just keep an eye on the airlock and I assume (perhaps dangerously) that a few days after airlock activity ceases that the ale is done.
If I'm making a lager, or something with a higher OG, or both, then I'll do things like give the beer a little extra time (perhaps 3 weeks or a month) and take a gravity reading at that point. If after that it is at or below what I expect, I rack or bottle. I don't take a reading every day for a few days to see if the beer is stable, I just assume (perhaps dangerously) it will be or that it will be close enough that it wont matter.
Get a wine thief. They'll fit in anything larger than a 1-gallon jug.