I'm with you, Red. The very first thing I thought of was 'sailboat'. Then I think I'd go for a summer home in Bayfield, Wisconsin and a winter home where ever my grandchildren are. I have very simple tastes. :o)
Yeah, sailboats are fantastic. I only first discovered them last week. They're quite easy to use, and one of the most enjoyable activities I've experienced in a long time. As of yet, I have no winter preference... but it would have to be somewhere warm inside the continental US... though some day I'd like to take a tour of historic Europe...
With a name like "Lakeside", what else? :)