My Mum and Dad have always had sailing boats, culminating in them spending 12 years building a 47' Steel Ketch. Sad thing was, by the time they had finished building it (both had demanding jobs) they were almost too old to enjoy it.
They sold it a few years ago, lost loads of money on it because it was right in the middle of the "luxuries slump". Sailing is lovely, when you are off the coast with the engines off it is very serene, but it does take bloody ages to get anywhere.
My gf's father is a very successful quarry owner down here in the South, and hes got a 53' Sunseeker. That thing is bonkers, so quick, I see the attraction but trust me, unless you are seriously minted, the cost of filling up the tanks would cripple you....and one blat around the local area is Very expensive. Bloody cool though when you pull up somewhere in it, its straight outta Notorious BIG videos....very gangsta don't you know.