How to plan a multi-city trip without wrecking it
Multi-city trips fail in predictable ways: too many stops, nights that don't add up, and travel days that quietly eat half the holiday. Here's the method we built into ConMigo, written out so you can sanity-check any itinerary — ours included.
1. Count nights, not days
A "7-day trip" is six nights, and nights are what you actually allocate between cities. The day you travel between stops belongs to neither city — checkout, transit, check-in and re-orientation reliably consume the useful hours. So the first honest question is: six nights across how many stops?
2. The minimum-nights rule
Two nights is the floor for any stop you care about — one night gives you a single evening and a rushed morning. Three nights is the floor for a big city (Rome, Tokyo, Mexico City). Work backwards from that:
| Trip length | Stops that fit honestly |
|---|---|
| 5–6 nights | 2 stops |
| 7–9 nights | 2–3 stops |
| 10–13 nights | 3–4 stops |
| 14+ nights | 4–5 stops |
If your plan violates the table, cut a stop rather than shaving nights everywhere. A city you didn't visit is a reason to come back; four cities you barely saw is just an expensive blur.
3. Every base move costs half a day
Changing hotels costs more than the train ticket: pack, check out, transit, check in, find your feet again. Budget half a day per move, minimum — more if there's an airport involved. Three moves in a week means you've spent a day and a half of a six-day trip in logistics. This is why the day-trip test matters:
4. Order stops by geography, then by intensity
Route your stops so the map reads as one line, not a star — backtracking to a hub you've already stayed in is the most common wasted day we see. Two refinements:
- Open-jaw flights (into city A, home from city C) usually cost little more than a return and delete an entire backtracking day.
- Altitude and pace: if one stop is physically demanding (altitude, hiking, heat), put it second — arrive somewhere gentler first. It's why we recommend Arequipa before Cusco.
5. Give the last stop a real evening
Don't end on a travel day into a city you'll never see. Either finish with two nights in the final stop, or make the final stop the airport city and accept it's a logistics night. The worst ending is arriving somewhere wonderful at 21:00 the night before a 09:00 flight.
6. Sanity-check the total
Before booking anything, add it up: nights per stop + travel half-days must equal your trip length with nothing left over and nothing negative. It sounds obvious; it's also the single most common planning error we see (an 11-night allocation inside a 5-night trip, in one memorable case). If the arithmetic doesn't close, the itinerary is fiction.