How to plan a journey across several countries without it becoming a relay race

When a border adds rather than subtracts

The best multi-country journeys usually rest on one of two logics. The first is continuity: a landscape or a river ignores the border, and the journey simply follows it. The Mekong flows from southern Vietnam into Cambodia, so going upriver by boat from Chau Doc to Phnom Penh becomes not a transfer but one of the most memorable days of the trip. The Altiplano begins in Chile's Atacama Desert and carries on across coloured lagoons to Bolivia's Salar de Uyuni – the border is just a halt along the way. The Peaks of the Balkans trail winds through the mountains of Albania, Kosovo and Montenegro, and from Singapore the railway runs north through Malaysia.

The second is contrast. Sri Lanka and the Maldives are completely different journeys: one of temples, tea hills and trains, the other of lagoon and doing almost nothing. That's exactly why they pair so well. The first part gives the trip its substance; the second gives you time to take it in. The key is that the contrast is clear: two similar beach countries back to back usually add little more than another flight.

Each country has to earn its days

Every new country costs time, even when the plan doesn't show it: a flight or a border, the journey to the first night's stay, a first evening spent finding your feet. So a rough guide is at least four or five nights in each country. Less than that usually means the crossing eats up most of what the country could have given you.

With typical annual leave, this matters all the more. With two weeks, two countries is usually the limit, and only when a short, smooth crossing joins them. Three weeks leave room for a second country and some rest at the end. Three countries in two weeks almost always means you haven't really seen any of them.

If a border adds nothing, it simply takes away a day.

Joining the pieces

• Fly into one city and out of another. A long-haul flight into the first country and home from the last saves retracing your steps – often a whole day.
• Go overland when the journey itself is the experience: by river, by rail, on foot. Fly when distance is just distance.
• Order by altitude and climate. The Atacama–Bolivia route starts in San Pedro de Atacama, where you can adjust to altitude before climbing onto the Altiplano. It's worth talking to a doctor before journeys like this.
• Order by energy: the more active or intense part first, the rest at the end. After Sri Lanka's Cultural Triangle and hill country, the Maldives feel like a reward; the other way round feels like being woken too early.
• Leave room around borders. Crossings, internal flights and boats don't always run to time, so avoid scheduling a fixed-date highlight straight after one.

Some journeys deserve a day of their own. The train from Kandy through the tea hills to Ella in Sri Lanka isn't a way of getting to the next place; it's one of the reasons to go. If a day like that is on your route, plan it slowly and don't try to fit anything else in.

Seasons rarely line up perfectly

Two countries often means two climates. In Sri Lanka, the rains usually reach different coasts at different times; the Maldives have their own dry and wetter rhythm; and on Bolivia's Altiplano, the cold, dry winter nights and the wetter summer differ enough to change the whole character of the trip. Usually you choose a time that is good for both, even if it's perfect for neither. That's normal – it's just worth knowing in advance and arranging the parts accordingly.

What to keep for next time

The hardest part of a multi-country journey is leaving things out. Laos looks right next to Cambodia, Peru right next to Bolivia, and every extra dot on the map looks like an opportunity. But a journey that fits everything in often has room for nothing. Ask yourself: does this country add something new, or just another stamp? If the answer isn't clear, it will probably keep for another trip – and get the time it deserves.

Tell us which countries you'd love to combine and how much time you have. Together we'll look at which links are natural, and which are better kept for separate journeys.