If you're staying on the West Coast I'd recommend getting below Tampa Bay. Even this far south it still gets cold. The keys have some excellent cruising, though the prices (and the 10% sales tax!) can be pretty steep.
There was recently a law passed in FL protecting cruising sailors rights to anchor and stay for extended periods of time. So long as you have your registration numbers and a working anchor light you should be fine.
Look up the "Shark River" near Cape Sable. It's supposed to be an excellent remote winter anchorage in the Everglades National Park. It's also about a days run down (marked) Channel 5 to the Keys, with one of the few bridges tall enough to let a sailboat pass to the Atlantic side (Hawks Channel) at the end.