The sailboat is IMO the single best prop a guy can have. It helps to know how to sail, but 90% of the time I use the boat, I never leave my slip.
I bought an old Columbia 40 sloop, fiberglass hull with mahogany accents, for pennies a few years ago -- it had had a fire in the galley and needed a new interior, and the owner was dumping it. I pimped it hard: 5.1 surround, modern galley with stainless fixtures and a wine rack, huge hot water heater, filtered tap water, comfy furniture, reworked all the interior trim -- and I maintain it meticulously. I think of it as having 80 feet of waterfront property for the price of a good used car. I don't live aboard, but I spend a lot of time on it. Since it's an old boat, I can always be "working on it," which keeps it looking nice, as well. A bottle of wine, some jazz on the stereo, a sunset. . . .