Plan an entire trip from a rough idea to a realistic day-by-day itinerary
Most trip planning jumps straight to an itinerary before deciding what the trip is even for.
- Outcome
- A day-by-day itinerary that accounts for real travel time and energy, built on a wishlist that's actually been prioritized.
- Time
- 1-2 hours across a few sessions
This workflow is part of PromptKit Pro
A handful of prompts and workflows stay free for everyone — Pro unlocks the full library, including this one, plus the guided runner.
Trip planning often skips straight to building an itinerary from a wishlist of sights, without first getting clear on what the trip is actually for, packing the wishlist into more time than exists, or honestly weighing where it's worth spending more money. This playbook runs those steps first, so the final itinerary is built on something real instead of a generic list of things people say you should see.
When not to use this
For a simple, short trip or one where you genuinely want to wander without a plan, this much process works against what you actually want. This is for a trip complex enough that planning it well matters.
Did this work?
You could actually execute every day of the resulting itinerary, including realistic travel time, and it reflects what you actually want from the trip, not a generic top-10 list.
Tested on claude-opus-5. Evidence status is draft; it moves to battle-tested only on recorded runs, never by hand.