San Diego, California
Locals sometimes joke that a thermometer is a waste of money in San Diego. Chances are good that if it’s not summer, the skies will be clear and sunny and the temperature will be hovering somewhere in the 60s or 70s. Oddly, though it remains warm in the autumn and winter, San Diego is not terribly hot in the summer either, making it a good destination just about year round. But if 70 degrees and sunny sounds good to you as you huddle around your fireplace, San Diego may be a great choice to get away from it all. While there will be a greater chance of rain during the winter months in San Diego, there is still significantly less rainfall during this time of year in San Diego than in most Eastern cities.
The Florida Keys in winter are also very predictable. If the temperature happens to dip down into the 50s, which happens occasionally, locals will be bundled up in coats, hats and gloves while visitors will probably be strolling about in long-sleeved t-shirts and enjoying the relative warmth. The most likely weather in the Keys in winter, however, will be sunny and in the 70s. Daily rain is nearly a given, though a thoroughly soaking all-day rain happens only occasionally. The Keys also offer many winter vacation options, from very, very relaxed (Sugarloaf, as an example) to hard-partying (think Key West).