A multi-city trip dies in the cracks: a landing at 22:40 with a non-refundable countryside inn ninety minutes away, or a flight home that leaves from a city you have not reached yet. The booking order is the product. Flights and the first and last hotels are one decision. The pretty middle is allowed to stay flexible a little longer.
An open-jaw ticket — fly into one city, home from another — is often cheaper in sanity than a round trip plus a positioning flight. Compare it against two one-way tickets before you assume the round trip is the grown-up choice. One-way fares on different airlines can be a bargain and a gift to your future self when a delay does not void the return. They can also be two separate customer-service problems. If the trip is a wedding or a tour with a date you cannot miss, the single ticket with protection you understand may be worth more than the clever fare.
Leave a buffer night
Do not schedule the important thing for the afternoon you land, especially after a transoceanic flight. Book a simple hotel near the arrival airport or the first station, cancellable, and let the first evening be a shower and a meal. Use the same kindness on the way out. A countryside checkout at 10:00 and an international flight at 13:30 is how people learn the local word for “delayed train.”
Self-transfers — separate tickets that only connect because you believe in yourself — need a longer gap than a single itinerary. You may have to collect bags, change terminals, and clear security again. Three hours is a minimum in a familiar airport, not a rule for a winter connection in a terminal you have never seen. If you would cry missing the second flight, do not self-transfer.
A sequence that holds
Fix the long-haul flights. Fix the hotel on night one and the hotel on the night before departure, both with dates that match the actual landing and the actual departure, not the spirit of the day. Then book the trains or island ferries that sell out. Then book the special dinners. Then, and only then, fill the middling hotels. If a middle hotel is prepaid and strict, you have turned a flexible week into a chain of penalties. Keep at least one stay in the middle on a free-cancellation rate until the trains are real.
Write the confirmation numbers into one note you can reach offline. When a delay happens, you will not want to search five inboxes on a station platform. The trip you booked is the trip you can rebook. That is the entire craft.