I've always been fascinated with sailboats. As a kid, I spent a week at camp, and the highlight of that week was sailing small Sunfish sailboats. I have briefly owned a couple of Hobie Cats over the years, but both were very short lived and I never really learned to sail properly. Just recently (7/05) I bought a small daysailer (an American Fiberglass "Kingfisher") to teach myself to sail. I've only had it out a few times, but so far, so good. The plan is to get a larger weekender type sailboat in the future to take the kids along (#2 due in October!), but for now the Kingfisher is being a good teacher.
My father gave me his old 14' jon boat a couple of years ago, but I never got around to using it even though I live just a couple of miles from the Elk River, right at the head of the Chesapeake Bay. This summer we decided to take our 2 year old daughter out on it and she loved it. We all had fun and it got us thinking about a slightly more comfortable boat. The jon boat is fun, but w/a 4hp motor, it doesn't get anywhere in a hurry. We'd like to be able to go to a few different local places via the water, but it would take all day on the jon boat. Enter the 16' Galaxie bowrider. It's just an old boat, but it provides more opportunity for fun on the water, and fun is good.
I also have an Old Town Otter kayak. It's a low-end recreational kayak, but it suits my needs/skills just fine. I enjoy poking around and exploring little places that I couldn't get to in a bigger boat or on foot. It's the simplest boat I have, but it's not any less fun than the others.
So there it is... I currently have four boats. They each do something that the others can't, and that's what makes them all fun. I don't recall there being any rule about only having one anyway... ;-)