A multi-city business trip looks fine on the calendar and falls apart in reality, usually somewhere around day two. The claim worth defending: these trips collapse not because of bad luck but because they are sequenced by geography and packed to the minute, so the first delay cascades through every remaining meeting.
Sequence cities by meeting priority
The instinct is to order cities by what makes a tidy travel route. The better rule is to order them by which meeting matters most, and schedule that one early — ideally the first full day, when you are freshest and before anything has had a chance to slip. If the trip degrades, it degrades into the low-stakes meetings at the end, not the deal you flew out for.
The buffer rule for each connection
Every connection between cities needs a buffer proportional to what it feeds. A tight 90-minute airport connection is fine when it leads to a rest day; it is reckless when a signing meeting sits on the other side. The working rule: for any leg followed by something that cannot move, budget at least half a day of slack. Slack feels wasteful right up until the one time it saves the trip.
Carry documents in three places
Tickets, hotel confirmations, meeting addresses and visa paperwork should exist in three independent places: printed, saved offline on your phone, and in the cloud. The failure mode is predictable — a dead battery in a taxi in a city where you do not speak the language, with the only copy of the address on the dead phone. Redundancy costs five minutes before you leave.
What to do when the first leg slips
When the first leg is delayed, do not try to absorb it silently into the schedule. Reach the highest-priority contact affected, tell them early, and rebook from the current reality rather than the plan you had this morning. A meeting moved with three hours' notice is a minor adjustment; the same meeting missed with no warning is a relationship cost.
Single-reference itineraries
The whole trip should live in one place, not scattered across email threads, screenshots and a booking app per city. One document — flights, hotels, meetings, contacts, buffers — that you can read at a glance and that updates when something changes. Building that single, stateful itinerary is exactly the kind of tool we design on our travel service.