The usual method is to see a photograph, decide on the place, and then find out what it costs and whether the month works. That sequence produces a lot of trips that are technically the trip you booked and not the one you wanted.
Working the other way round takes an afternoon and produces better trips.
Start with the constraint that cannot move
For almost everyone that is when, not where. School holidays, annual leave, a fixed window between jobs.
Fix the dates first, then ask what is genuinely good in those weeks. It is a much shorter list than it feels like, and it eliminates most of the ways a trip disappoints.
Some hard seasonal facts worth having in front of you:
- Patagonia is closed for half the year.
- Southeast Asia’s mainland and Indonesia have opposite dry seasons.
- The tropical Andes and Patagonia have opposite seasons within the same continent.
- Northern Australia is unvisitable in its wet season while Sydney is at its best.
- India’s plains in May are 45°C; the Himalaya are perfect.
- The Serengeti’s migration is somewhere different every month.
- Victoria Falls is either invisible with spray or half dry, depending on the month.
If your dates are August, a great deal of Europe is at capacity and much of Asia is under monsoon, and the honest answers are Scandinavia, the Baltics, Japan’s north, southern Africa, or Indonesia.
Then the second constraint: how long
The number of days determines how far you can usefully go, and the arithmetic is unforgiving.
A week means one country, ideally one region, no more than one internal flight, and somewhere reachable in under about eight hours’ flying. A week in Jordan works. A week in Peru is three days of it in transit.
Two weeks means one country properly or two adjacent ones.
A month opens up long-haul multi-country routes.
Three months or more and the constraint stops being time and becomes money and visas.
A rule that holds up: subtract two days for travel at each end, and then plan for two-thirds of what remains, because you will want the other third.
Then budget, by region rather than by day
Daily-budget figures are close to meaningless across regions that differ by a factor of five. Think in bands instead:
Cheapest: South Asia, Southeast Asia, Central America, the Balkans, Egypt, Bolivia, Turkey.
Middle: southern and eastern Europe, Morocco, South Africa, Japan, Korea, Argentina, Mexico.
Expensive: western and northern Europe, Australia, New Zealand, the Gulf, Chile, Costa Rica, Botswana, Iceland.
A different order entirely: Antarctica, Galápagos cruises, gorilla permits, Bhutan.
The flight is frequently the largest single cost, which means a cheap destination that is far away can total more than an expensive one nearby. Compare totals, not daily rates.
Then, finally, what you actually like
The question worth answering honestly: what did you enjoy most about the last three trips you took?
Most people’s answer is one of about six things — eating, walking, looking at old things, being in landscape, being in water, or being somewhere that feels unlike home — and it is usually not the thing they say when asked in the abstract.
If the answer is food, choose by cuisine and put the sights second: Vietnam, Mexico, Japan, Italy’s south, Turkey, Peru.
If it is walking, choose by trail and season: the Alps, Patagonia, Nepal, the Dolomites, Madeira.
If it is old things, choose by density: Jordan, Sicily, Greece, Egypt, Peru, Turkey.
If it is being in landscape, choose by emptiness: Namibia, Iceland, the Faroes, Mongolia, the Scottish Highlands.
The test before you book
Three questions:
Is the season actually right, or am I hoping?
Does the number of days survive contact with the map — have I looked up how long the journeys between the places actually take, rather than how far apart they look?
Would I still want to go if I could not photograph it? This one filters out a surprising number of destinations that are famous because of a single image and are, in person, that image and a car park.
The mistakes that recur
Choosing from one photograph. A great many destinations are famous for a single view, and the honest question is whether the rest of the place holds up for the days either side of it. Some do. Some are that view, a car park and a two-hour drive back.
Ignoring the internal distances. Countries that look compact on a world map are not. Australia is the size of Europe. Peru is twice the size of France with mountain roads. Two hours on a map is frequently six on the ground, and this single miscalculation produces more disappointing itineraries than any other.
Booking the flight before checking what is open. Half the destinations in this guide have a season outside which the thing you are going for is closed, snowed in, dried up or has migrated somewhere else. Patagonia shuts. The Serengeti’s herds move. Victoria Falls is either invisible or half dry.
Assuming a country is one thing. India, Brazil, China, Indonesia and the United States are all continent-scale and internally various enough that “have you been to India” is close to a meaningless question. Choose a region, not a flag.
A worked example
Suppose you have two weeks in late October, a moderate budget, and you like walking and eating.
Late October rules out: Patagonia (season not open), northern Europe (dark and wet), Southeast Asia’s mainland in parts (end of the rains), and the Andes (wet season beginning).
It suits: Japan for autumn colour, Turkey, Morocco, southern Italy, Portugal, Jordan, Nepal for the clearest trekking month of the year, and the Caucasus.
That is eight candidates rather than the whole world, arrived at in about four minutes, and every one of them is genuinely good in that fortnight. Now the photographs are a reasonable way to choose between them.