Originally Posted by emcentar
Why only those places? Personally I want to retire in NYC (plenty to do, great culture, not trapped in your house if you get infirm or can't drive anymore) and take long sailing trips in various places, working through my bucket list. The Caribbean is beautiful but my sailing dreams more often put me in Turkey, sailing the Sea of Marmara or the Med.
I know NYC like the palm of my hand. But if I want to live in the City, I would take the Canadian Cities any time, like Toronto, Montreal or Vancouver. But I don't mind the cold, in fact I like it.