We both love beach cats and think that a cruiser will be part of our future. We just want to take "baby steps" on the way toward a purchase.
Yes, it's a great idea. Try to pick a day when the sailing and weather
are good. You need a few of those so you remember what it can be on those days it's not.
is training classes
and US Sailing have schools every place (well almost) and you can even do a course as a live aboard or some place near a place you want to go. It's a great way to sail real boats and learn about it. familiarity makes it comfortable.
If you can get through a charter or two and/or a class I would think you can decide if you like it enough to get into it more. The way to know for sure is it really all is supposed to be fun. If you can try different things and say it was a great time after each of them then it's probably a good fit.