I have been casually kayaking and canoing for most of my life. The area of north Florida I live in is wonderful for this with some really beautiful rivers and interesting coastline. I currently own a Klepper A2 with a sail kit, a Hobie Mirage, and a Hobie Outback with the sail kit.
I also own a Seapearl 21 a small cat ketch rigged boat. It's a wonderful boat. It's small enough to tow easily, but big enough to carry a lot of camping supplies. Fast and easy to sail.
My wife Christy and I host and produce a weekly sailing podcast at FurledSails.com