In five short bullets:
- brainstorming what must be considered (“I want to go somewhere warm for two weeks” is good but insufficient)
- making a high-level pass over the possibilities
- picking a main approach and making a mid-level pass to gather all the options
- Sifting those options and deciding what your trip will look like
- Grinding out the detailed plans that will make your days so much easier, and prevent problems from occurring
