Where oh where to retire to?

I have been thinking a lot lately about where I want to live part time once I retire. I plan on working for a couple of more years though but it is time to start seriously looking. I used to think that I would live part time on Isla Mujeres, MX. I have come to the realization that I do not want to be a remote home owner of a house in Mexico. Too many challenging things to deal with, FM3, managing remotely to have maintenance and repairs done on a home that by virtue of being on an island would be prone to debilitation from nature’s elements.

I had made an offer on a small condo last year but the builder would not negotiate on price. When I saw the finished condos in April I realized that they were much smaller than I even imagined and it was just not meant to be.

Then I toyed with making an offer on a private home on Isla but after a couple weeks thought the owner wants to sell because he lives in Canada and the large house is too much for him to manage by himself. His reasons for selling were what made me decide not pursue making an offer on his house.

When I visited with my friend Jane while on Sanibel she told me about the 55+ retirement community she bought a small home in outside of Phoenix. I looked at some of the communities online yesterday. I could get one of the small homes and add room or look for one that has already added a room for a reasonable price for a 2nd home. The homes are pretty tiny but the upside is outside living due to the warm temparure and dry climate. The downside is that some of these communities are huge and there is no beach close by. They have several communities in southern California and three in Florida but due to the high cost of living I don’t think they would be on the top of my list. Actually the one community in Tampa may be affordable but it is gigantic! This is one of the smaller communities in Arizona.

So my dilemma is where to start seriously looking for a reasonably priced 2nd home to spend 6 months or so a year at when I retire.

My lists of requirements are:
1. Close to an international airport so I can still travel to Isla Mujeres and get back to Portland relatively easy
2. I would love to be near a beach
3. Warm and sunny weather is a must since I live in Portland where it is often gray and rainy
4. Somewhere I do not have to totally rely on a car to get around
5. I would love to be able to afford a two bedroom home or condo so my daughter or friends could stay with me when they visit

Where is this retirement utopia? I will be looking for it over the next year or so. I want to purchase a place or rent year round prior to my retirement which will most likely be September 2009 when I will turn 55.

If you know of a place that fits my requirements let me know.