When I was younger my dad had a sunfish and it was fun taking it in the small lake in Texas. We then got a Catalina 22 and it felt like it was to big for that body of water. It felt like it got boring really quick as we would sail the whole body in less than a day. We would also spent most of our time tacking. Sometimes we would take us 30 minutes to get out and 2 hours to get back. The wind would normally be behind us as we went through the narrow strait that led to lake.
I am wondering is sailing a whole different experience when you can go to many different locations and be out for days? I have a 19ft Cuddy that I have been enjoying for over a year. I am wondering one day upgrading to a 35+ footer and going exploring on the weekends. I guess my main worry is getting bored with the larger boat. I might try crewing a race boat as that might help me decide.