TOD: Southern Portugal would probably be at the top of my list. I find the Portuguese language easy to pick up, plus there are so many retired Brits there that English is never too far away. But the Atlantic coast is just beautiful, the living isn't too fast paced (I was there in the off season, my mind may change if I were there in summer), the food is extraordinary, and the people are helpful and respectful without being phony.
Other places under consideration: the isle of Rhodes, Brazil, Spain's Costa del Sol ... yes, I like coastal places.