Multi-city trips get overplanned into misery or underplanned into missed opportunities. This workflow finds the middle: constraints first, then the right pacing across cities, then a per-city rhythm that leaves room for actual serendipity.
Constraints first
Goal: The specific constraints (time, budget, energy, non-negotiables).
Multi-city trip planning. Destinations under consideration: [list]. Total days: [N]. Travelers: [ages/mobility/interests]. Budget range: [range]. Non-negotiables: [must-have or must-avoid]. Give me a structured view of the constraints so we can plan against them.
Route + pacing
Goal: 3-4 base cities, minimum 3 nights each, realistic travel between.
Given the constraints: recommend 3-4 base cities within [destination], with nights per city + how you'd travel between. Rationale for each choice.
Per-city rhythm
Goal: Each city: 1 must-do per day + built-in flex.
For each base city: draft a daily rhythm that includes ONE must-do per day + explicit unstructured time. No color-coded 8am-to-10pm blocks. Better trips have negative space.
Repeatability, not cleverness.
What lives where when the workflow finishes.
Once the shape is set, book flights + accommodations first (they lock the trip). Restaurants + specific tours can go later. Leave 30% of days genuinely unplanned.
The same shape, different jobs.
- Family-with-kids version: swap 'one must-do' for 'one kid-friendly + one adult-interest' each day; more accommodation flexibility for meltdown recovery.
- Solo version: same structure but shorter — solo travelers often prefer 2-4 nights per base with more cities.
Try this workflow once. Then decide if it earns a recurring slot.
The value compounds after the third run, not the first.