Mark and Patti,
You haven't given us much info to work with, but your idea of chartering to "try out" boating and even different "types" of boats is a good idea.
Depending on the size of boat you are considering, the budget, how often you would use it, guests regularly or not, etc. may change drastically any recommendations.
However, to "test out" several different basic layouts you might charter Nordic or American Tugs, Grand Banks, Defever, Monk, etc., looking for forward cabin, aft cabin, mid ship cabin, etc. twins or single, etc. so as to see what you like.