Plan a multi-city trip with real logistics between stops
A great itinerary for each city individually can still fall apart at the transitions between them.
- Outcome
- A multi-city route ordered by real travel logistics rather than a wishlist's order, each transition between cities accounted for with realistic time and buffer, and a trip that holds together as one plan instead of several disconnected single-city itineraries.
- Time
- 2-4 hours across 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.
Multi-city trips often get planned one city at a time, each with a solid individual itinerary, while the transitions between cities — the actual travel days, connection logistics, what happens to luggage and energy levels — get left as an assumption that it'll work itself out. This playbook plans the route order based on real logistics first, then treats each transition as seriously as each stop itself.
When not to use this
For a single-destination trip, this multi-city logistics focus doesn't apply — a simpler single-location itinerary process serves better.
Did this work?
Every transition between cities has a realistic, planned logistics path, not just an assumption that getting between them will work itself out.
Tested on claude-opus-5. Evidence status is draft; it moves to battle-tested only on recorded runs, never by hand.