How to Plan Complex
Multi-City Travel Like a Pro

A well-planned trip is invisible. You arrive at the airport knowing your terminal, your bag drop time, and your lounge. You land in a new city and the car is waiting. The hotel knows your preferences. The dinner reservation is made. The presentation is printed and waiting at the venue. Nothing is uncertain. Nothing requires your attention in transit except the work you chose to do.

A poorly planned trip is the opposite: a series of small friction points that accumulate into a week of low-grade stress, missed opportunities, and avoidable waste. Here is the system I use to make every trip — however complex — feel like the first kind.

Step one: the travel preferences SOP

Before planning any trip, I document a Travel Preferences SOP for each client. This covers: preferred airlines and alliance memberships, seat preferences (aisle or window, quiet zones), hotel tier and brands, dietary requirements, car hire preferences, preferred payment and expense capture methods, and out-of-office communication preferences while travelling.

This document means that every trip is planned to the same personal standard without needing to ask the same questions each time — and it becomes more refined with every journey.

Step two: map the trip backwards

I always plan from the destination backwards to the departure point. Start with the commitment — the meeting, the event, the flight home — and work backwards from there. What time does the meeting end? When does the last flight leave? What is the buffer needed to get to the airport comfortably? What needs to happen at the hotel before checkout?

Planning forwards from departure means you are constantly checking whether everything fits. Planning backwards from commitments means you start with certainty and build the logistics around it.

The travel pack: what every trip needs

Before every trip, I prepare a single document — the travel pack — that contains everything needed from departure to return. It includes:

• Full itinerary with times, addresses, and contact names for every commitment
• All confirmation numbers, booking references, and check-in links
• Transport details including terminals, platforms, pickup meeting points, and driver contacts
• Hotel details including check-in time, room preferences confirmed, Wi-Fi details, and concierge contact
• Dining reservations with addresses and confirmation numbers
• Emergency contacts and local numbers (nearest hospital, Embassy if international)
• Contingency notes — what to do if a flight is cancelled or a meeting overruns

Managing multi-city complexity

Multi-city trips — London to Edinburgh to Manchester, or London to New York to Chicago to Toronto — require an additional layer of planning around connection buffers, baggage logistics, and the accumulation of small decisions across multiple cities and time zones.

The key principles: never book the last connection of the day if an earlier one exists at similar cost. Always build a 90-minute buffer on international connections. Confirm hotel checkout times in advance. And keep a live copy of the travel pack in a shared cloud folder that can be accessed from any device without relying on mobile data.

The out-of-office protocol

A client travelling without inbox coverage is a client who returns to 300+ emails and a week of catching up. Part of every travel plan is agreeing the out-of-office protocol: what Northern Desk handles in their absence, what gets flagged urgently, and how the client wants to communicate (if at all) while away.

The best trips are the ones where the traveller's only job is to show up and be present. Everything else is logistics — and logistics, done well, is invisible.

Debbie Jones is the founder of Northern Desk, an executive services practice.