Had boats all my life, mostly inboard ski boats, but now I have a old 19' center console sitting in salt water in FL and a pontoon in fresh water in MI. And my son keeps his ski boat at my dock in MI. BUT I would love to have a friend that has a sailboat...growing up my uncle had a wooden 24 footer up in Cheboygan MI that he would take out to Mackinac Island.
Edit: How could I forget? My wife grew up on a lake that had a small Sunfish club that raced every Sunday. Her dad had one that we ended up with. Sailed it a few years on our lake but too many weeds for the centerboard so we sold it. Got real involved with tournament slalom and trick skiing with my buddies and lost interest.