First, I would buy a beach cat, perhaps a Hobie Tiger. I miss small boats most.
Right on. Our current boat is a 19' trailerable, and though I plan on getting a larger cruising boat at some point, we don't intend to ever sell the small boat... too much sailing fun for such small coin. I also still windsurf now and then.
Back on topic, we just got back from a week in St Lucia, staying at Marigot Bay, where we saw a few of the boats that $100mil could buy.
One of our outings was a crewed day-trip south and back on a 40' Catalina. It was very relaxed and casual. At one point, as we were chatting away, the talk drifted to dream-boats, and we asked the 3 St Lucian crewmembers what they'd do with a million dollars. One young crewmember who is taking the courses toward being a charter captain, said he wanted to finish his education, get his own boat, and do nothing but sail.The boat captain said he'd want to have a boat big enough to take his church congregation for some cruising. One crewmember said she'd set up an orphanage.
So... lotto-winning or not, I'm just going to try to keep my fat white overfed face shut, remain grateful for all our advantages and blessings, make what donations I can.... and if good fortune ever drops a pile in our lap, I hope to have the grace to give the majority to help those in genuine need.
(Ok, a 35 to 40 ft cruiser would be pretty cool too)