Dumping the van is a great idea - well your van anyway - it's always breaking down...heh heh.
We spent last winter in Italy/Greece. This year we're in Turkey/Cyprus and next year, we'll do Spain/Portugal/Morocco. I guess you do run out of options, but there's no rule to say you have to stay in one place - even if you pick Spain, it's quite BIG.
Today it's 25 degrees in Southern Turkey. Took a lobster pot out in the kayak and fixed it to a buoy. Caught a bream and had that for supper. Somehow that took up most of the day...