Catalina 22's are inexpensive, there are a lot of them around, and they'll give you a little more of a 'big boat" feel than some smaller boats where you on the boat rather than in it. You can also sell it after a season for what you paid.
It might be a good idea to take a sailing course. Google ASA and US Sailing plus your area to find local schools. You can also look at schools such as the Offshore Sailing School that offer learn to sail vacations in warmer climates.
Best of luck,
95 Catalina 30 Island Time
“If a man is to be obsessed by something, I suppose a boat is as good as anything, perhaps a bit better than most" - E.B. White