Planning a Multi-City Business Trip

How to plan a trip that hits four cities in five days without falling apart — routing, booking, and surviving a week of different beds. From someone who has run the roadshow.

A multi-city trip is a routing problem wearing a travel problem’s clothes. Get the sequence and the buffers right and it hums; get them wrong and one delay topples the whole week. Here is how to plan one that holds.

How do I plan a multi-city business trip?

Start from the meetings, not the flights: fix the appointments that cannot move, then route the trip as a loop or a line that minimizes backtracking, ideally ending closer to home than you started. Book it as a single multi-city itinerary rather than separate one-ways where you can — it is often cheaper and keeps you in one reservation if things change. Give every leg a real buffer, because in a multi-stop trip a delay does not cost you one meeting, it cascades into all the ones after it. Sequence by geography and by energy: put the highest-stakes meeting where you will be sharpest, not on day five after four hotels.

How do I handle a week of different cities?

Treat consistency as the thing that keeps you functional. Pack once for the whole week in a single carry-on so you are never at a baggage claim between meetings, keep a repeatable daily rhythm even as the city changes, and build one genuine recovery point into the week — an evening with nothing scheduled — so the fatigue does not compound into a bad meeting. Log notes and expenses at the end of each day while it is fresh, because by city four they blur together. And protect sleep ruthlessly; a week of different cities is won or lost on whether you arrive at each one able to think.

How do I route a roadshow efficiently?

Route it the way you would solve a traveling-salesman problem: cluster stops by geography, move in one consistent direction to avoid crossing your own path, and let flight availability and meeting times — not just the map — shape the order. Prefer direct flights between stops even at a higher fare; on a roadshow, a saved connection is saved risk, not just saved time. Anchor each overnight where the next morning’s meeting is, so you are never racing in from another city at 8 a.m. And leave one flexible slot: roadshows always sprout a meeting mid-trip, and a route with no give cannot absorb it.

Is a multi-city trip cheaper than separate trips?

Usually yes, on both money and time — one trip that chains four cities avoids three sets of round-trip airfares home and three separate travel days, and a single multi-city fare is often priced better than four one-ways. The catch is that it concentrates risk, since one bad delay hits everything downstream, and it is harder on the traveler, so the saving is real only if the trip is planned with enough buffer to actually hold together. As a rule: chain the trip when the cities are near each other or the meetings cluster in time; split it when the stops are far-flung or each one is important enough that you do not want a shared point of failure.

More answers for the road in the Field Guide.