Traveleogy
Fewer places, better days

Planning

Choosing a destination when you have no idea

Starting from a list of places produces poor decisions; starting from constraints produces better ones.

Explore destinations with a compass and passport on a world map. Perfect for adventure planning.
Explore destinations with a compass and passport on a world map. Perfect for adventure planning. · Photo via Pexels
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Deciding where to go is generally approached as a matter of inspiration and is better handled as a matter of constraint.

Start with the constraints

Four questions narrow the field enormously.

When can you go? Which eliminates destinations in their monsoon, their extreme season or their peak crowding, and identifies where the timing happens to be ideal.

How long? Which determines how far is reasonable.

A week is generally not worth a very long flight, since two days are consumed by travel and jet lag occupies more.

What is the budget? Which affects distance and destination equally, since cost of living at the destination frequently matters more than the flight.

What do you actually want? Rest, activity, culture, food, landscape, heat, cold, company, solitude.

Most people can answer this and rarely do so explicitly, which is why itineraries frequently do not match what the person wanted.

Starting from the season

A useful inversion.

Rather than choosing a place and then a date, take the dates you have and ask where is at its best then.

Every month has destinations at their peak, and the resulting list is generally more interesting than the one produced by starting from a wish list.

It also means arriving somewhere in good conditions rather than in whatever the destination happens to be doing that month.

Starting from a specific thing

The approach that produces the most memorable trips, according to most people who travel a great deal.

A festival, a natural event, a specific dish, a route, a museum, a sporting occasion, a season.

Having a reason produces structure, and the rest of the trip organises around it naturally.

It also produces the encounters that a general sightseeing itinerary does not, since a specific interest connects you to people who share it.

The cost consideration

Frequently misunderstood.

The flight is the visible cost and is frequently not the largest.

A cheap flight to an expensive country produces a more expensive trip than a costly flight to an inexpensive one, for anything beyond a few days.

Which means the useful comparison is total cost for the trip length rather than airfare.

Exchange rate movements also matter and are worth checking, since a currency that has weakened substantially changes the affordability of a destination considerably.

The overlooked options

Where the value generally is.

The second and third cities of countries whose capitals are heavily visited, which are frequently more interesting and much cheaper.

Neighbouring countries to famous destinations, which offer comparable landscape and culture with a fraction of the visitors.

Domestic travel, which most people underuse, and which removes flights, visas and language barriers entirely.

Places recovering from a period of reduced tourism, where visitors are welcomed and prices are reasonable.

Anywhere in shoulder season, discussed elsewhere on this site.

The research that helps

Beyond destination lists.

Reading something written by someone from the place rather than by a visitor, which produces a different picture entirely.

Looking at a map properly, including what is nearby and how things connect.

Checking what is happening there during your dates.

And asking someone who has been — specifically what they would do differently, which produces more useful information than what they enjoyed.

The decision itself

A practical note.

Extended deliberation over destinations is a common way of not going anywhere.

Most destinations reward attention, most trips are what you make of them rather than what the place provides, and the difference between the third and fourth choice is generally smaller than the difference between going and not.

Which is an argument for deciding and booking rather than for continuing to research.

The repeat visit

An option that receives too little consideration.

Returning somewhere you have already been is frequently better than going somewhere new: the orientation is done, the disappointing parts can be skipped, and the depth available on a second visit is considerably greater.

People who travel a great deal generally have a small number of places they return to repeatedly, and describe those as the ones they actually know.

Which is worth weighing against the assumption that every trip should be somewhere new.

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Joon Park
Editor, Traveleogy

Joon has spent fifteen years travelling on other people’s deadlines and now writes for readers with two weeks of leave and a fixed budget.

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