Lots of good info in the links that Carol posted (and thanks for the video plug Carol!).

Feel free to come back with specific questions after wading through all the previous posts.

One note about chartering a "small" monohull. At The Moorings at least, you probably won't find anything smaller than a 45. They used to have a 43 but they are being phased out for the 45s. I only have experience with The Moorings however so other places might have smaller boats.