CFG,
Here is a recent (this fall) figure for chartering a 34ft cat for 7 nights out of the Ft. Myers area, 2 1/2 hrs from home.
Boat, insurance (required), trip cancel insurance 2739.00
We did not factor food because it is about the same as our local stores. More for beer though.
The worst part, except for having to return on a schedule (last day motoring against head wind and tide = yuk) was hauling all the stuff off the boat up to the car. It seemed so much easier when we were loading the boat
even though there was a lot more food and beer on the "to" trip.
I have been figuring what I would like to have and never will, but if I become a little realistic then a realistic figure for me to own and keep this same boat would cost about 10k a year. So I could charter 2-3 times a year.
If I owned the boat I could use (does working on it and scrubbing it count?) it a lot more than that in the same general area/type of sailing.
One bit of data for you.