Given that I haven't figured out what you do, I am at a loss to understand why you can't go whenever you want. Anyway, have you seen what's happening in Europe? El Nino hotsy-totsy. It might be a warm winter.
What do you want to do? See historic sights or frolic in the sun? Do you want nice hotels or is just about anything with a deb and a shower good enough for the night? Do you want somewhere with night life or a quieter type trip?