I've got a 25 foot macgregor, haven't been on it in years. Life got busy and it got put on the back burner. However i absolutely love sailing, there's nothing better in the world for me. The silence and violence of it is awesome, all contained by ropes. Me getting into sailing was the impetus for me learning splicing and more rigging, tree work followed shortly after. I'm pretty landlocked being in central Illinois, so I've only been on the Illinois river and the Peoria lakes (wide parts of the river that are lakes). I've been told if you can maneuver in a busy channel with idiots that don't understand who has the right of way under light airs just about everything will seem easy after that. Although there are very big lakes within driving distance, it always seemed too much hassle when i would rather just go on the water and party. I've wanted to take the boat back to lake Michigan (the boat has done the mackinaw race twice), but just never got around to it. If i went through it really well and fixed some of the stuff that needs attention, i could easily trailer it there, or Florida for that matter. As the kids get older I'm sure il get back into it, as boating is an awesome family activity. My sister just bought a sunfish, so i might go out on that this year.
The other really cool thing about sailing is the history of it, because that's really the history of rope and rigging. For the last century sailing has had the connotation of a way for the rich to blow money, but for most of human civilization it has been almost exclusively in the hands of the working class. A vast majority of knots, splices, tools and techniques for all manners of rigging were developed by illiterate sailors who used rope to pass the time rather than reading. Just about every "advancement" in tree work is actually centuries old technology and techniques used with modern materials. The grcs, friction devices, rigging rings, saddles, etc. are all directly from sailing.
Il have to hunt for more pictures, but here's one of me years ago in my driveway using the boom to determine how big the yellow jacket nest in the mast was during spring cleaning...