Multi-City Itinerary Planner

Pick 2-4 cities and how long you want to travel. We'll search every reasonable start date and every order of visiting them to find the combination where each city lands in its peak climate window. Search runs in your browser — no backend, no signup.

Trip Itinerary
whenrome.com/itinerary
City 1
City 2
City 3 (optional)
City 4 (optional)

Optimal itinerary

Pick at least 2 cities to see your optimal itinerary.

How the search works

For every possible start date (we sample weekly, so 52 candidates across the year), we try every order of visiting your cities — that's 6 orderings for 3 cities, 24 for 4 — and split your trip length evenly across the legs. Each leg gets a climate score based on the weighted average of conditions during the days you'd be there. The combination with the highest total score wins.

The score weighs whatever vibe you picked: balanced rewards mild temps and low rain; beach rewards warm and dry; ski rewards cold and snowy; explore rewards mild conditions with low hazard risk. Peak hazard seasons (hurricane, monsoon, etc.) always penalize the leg's score.