How to plan a multi-city trip without wasting days

A trip through several cities looks wonderful on a map and can feel like a series of stations in practice. Every extra stop adds a packing day, a transfer and a first evening spent finding dinner. The skill in a multi-city trip is choosing fewer places, putting them in the right order and making the moves between them painless.

Start with how many days you have

Count the days first, then decide how many cities fit. As a loose guide, a place needs at least two nights to be worth the move, and three if it is big. Ten days is comfortably three places; it can be four if the journeys are short and you like to keep moving. If you do not know how long to give each stop, how many days to spend in each city has the method.

It is nearly always better to cut a city than to give everyone a single night each. You are paying to travel, so you should see something when you arrive.

Choose cities that connect

Pick places that are easy to get between, not just good places. Look at a map and at the transport links, and choose a line, not a scatter. Good routes follow an existing rail line, a coast, a river or a motorway; bad ones double back.

Ask how you will get between each pair of stops, and about how long it takes door to door. Trains between city centres are often quicker than flying once you count the airport; for longer distances, flights win. For routes involving islands, ferries can run on a limited timetable. Find the real connections, not the ones that look plausible.

Order the route to avoid doubling back

Write down your candidate cities and draw the shortest sensible line through them. Look for a route that ends somewhere different from where it starts. This is the idea of an open-jaw trip: fly into one city and home from another, so you never retrace your steps. It can save a whole day, and sometimes costs little more, though that depends on the routes and the airlines, so compare before deciding.

If you must return to where you began, loop round rather than going out and back along the same line.

Put the hardest move at a time you can cope with

Long journeys are tiring, so do not schedule one right after an overnight flight or on the day of a big sight. Put the longest transfer on a day with nothing else planned, and treat it as the day's main event. A smaller transfer can sit alongside a morning of sightseeing, but not the other way round.

Think about the order of the places by mood too. Start with a place that is easy to get around if it is your first time abroad, and save the one that needs more energy for when you have settled in.

Pick your transport for each leg

For every leg, compare door-to-door time, cost, flexibility and what you can do on the way. A train gives you a window and room for luggage; a flight is faster over distance but adds airports; a coach is cheap and slow; a car suits places where the journey is part of the point.

Booking varies by mode. Some trains need seat reservations, some ferries fill early in summer, and some flights are cheaper far ahead. How far in advance to book goes through it, and train travel in Europe covers the rail side if your route is on that continent.

Choose where to sleep with the next move in mind

When you have a morning train, a bed near the station saves a taxi and a stressful hour. When you stay for several nights, location matters more for sights and food. A mix is fine: choose a central stay for the long stops and a practical one for the stopovers.

Check each night: do you have a bed, and can you check in when you arrive? If your train comes in late, make sure the accommodation knows. Late arrivals are a common problem.

Pack for moving

A multi-city trip means carrying your bag onto trains and up stairs, repeatedly. Pack smaller than you would for a week in one place. Choose one bag you can lift easily, clothes that mix and wash easily, and leave the extras behind. A packing list that knows where you are going helps you keep it light.

Keep the things for the move itself in a small bag at hand: tickets, charger, water, a layer, and anything you need on the way.

Keep one plan for the whole route

With several cities the amount to remember grows quickly: addresses, tickets, check-in times, a train platform. Keep it all in one place with the days, so each day shows where you sleep tonight and how you get to the next place.

A sample way to check it

Write one line per day: city, how you got there, where you sleep. Read the list from top to bottom and ask:

• Is there a day with no bed or no way of getting out of town?
• Are there two moves in two days?
• Does any move arrive late at night in a city you do not know?
• Does the route go in one direction?

Fix the ones that fail, and the trip becomes much easier to live.

Handle the money in one place

Several cities can mean several countries and currencies. Decide how you will pay in each and how you will keep track. If you are splitting costs with others, log them as you go in one trip currency rather than trying to add up receipts at the end.

What to do next

Write your cities in a line on a map, count the nights, and cut one stop if it feels tight. Then book the transport that is hardest to change first. If you are planning something shorter, a weekend city break is a simpler place to practise.