My method

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 
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