Thailand
Bangkok
The best street food on the planet, and a transport system that makes the chaos navigable. Stay 3–4 days, or 5 with a day trip.
The cheapest month to fly almost anywhere, and the best month to be somewhere dry and warm while home is grim.
Southeast Asia is in its cool dry peak and the Rockies are deep in ski season. Europe is cold and quiet — great for museums, bad for terraces.