Sicily struck a cord with me. I would love a part-time residence there, where I'd stay from March to May, then mid-September to mid-December. As a dream, I'd spend the summer months of June to mid-September in Canada and December to March in a sunny spot, like Hawaii (island of).
The reality is that I'm quite happy renting for extended stays. Every year, I try for one trip to Europe, often two. Every second winter, I'm already spending 8 to 11 weeks in Hawaii, between January and March (odd years). 2015 will be my 4th stay, for 9 weeks. In even years, I try to spend up to 10 weeks in one trip to Europe. I'm currently into week 2 of 8, this time.
When DH and I started discussing where and how we wanted to spend our retirement, we came to the realization that neither of us would completely retire, but both can be mobile for extended periods. Oddly enough, we had both really liked the Extremadura region of Spain and it was the first time that we entertained the notion of buying a second home in Europe.
Then Sicily tempted us. Hawaii actually had us looking at the market in earnest. Crete is appealing and doable as well.
What we have slowly come to realize is that rentals are easy to come by for when and where we enjoy spending time. They are ultimately cost-effective and low-risk. It's also far more convenient to plan around life events and changing needs if we are not tied to a place we own. I see the appeal in going back to the same place, as James does, and I'm slowly developing that connection in Hawaii.