I know Plakias very well lived there for 11 years. Because of my work I moved to Rethymno. I would like to recommend Plakias here for overwintering holidays. There a many sunny days on the south of Crete and untill December you may encounter the beach for swimming and sunning. The place is less crowded of course, but because the locals live there and are not moving back to the cities in the winter, there is also some nightlife with taverns and bars that stay open. Accommodations, with heathing are available, like Anna's and Koules and Zambia. Also Morpheas or many other places that can help you with good rates for longer periods. Than from Januari when spring is making the country like a postcard you can make beautiful walks in the area. See the farmers, collecting their olives, maybe give them a hand and get some oil for your help. If you have no job obligations, why not change your rainy or cold place for a few months in Spring on Crete and come to Plakias, where the summer never ends.
http://groups.msn.com/CreteHolidays