How to choose a holiday destination

Updated 2 June 2026 · by Marco Devlin · 7 min read

A world of options sounds wonderful until you're staring at it, unable to decide. The trick isn't to see everything — it's to ask the right questions in the right order, so the choice narrows itself. Here's the approach we use.

1. Start with the feeling, not the map

Before you look at a single destination, decide what you want this trip to feel like. Rest and warmth? Culture and energy? Wild landscapes and fresh air? Time with people you love, or time to yourself? The best destination is the one that delivers the feeling you're after — everything else is detail. Our Trip Style Finder is built around exactly this: it starts with the mood and works outward.

2. Let the season do half the work

Timing quietly decides whether a place is magical or miserable. The same destination can be glorious in one month and unbearable in another, and travelling in the shoulder season — the weeks either side of peak — often means better weather-to-crowd ratio and better value. If your dates are fixed, choose a destination that shines then; if your destination is fixed, choose the season that flatters it.

• Match conditions to your trip: sun for a beach week, snow for skiing, mild and dry for city walking.
• Mind the extremes: rainy seasons, heatwaves and peak-holiday crowds can define a trip more than the place itself.
• Favour the shoulders: quieter, often cheaper, and frequently the most pleasant weather of all.

3. Weigh travel time against trip length

A long journey can be worth it — or it can swallow a short break whole. As a rough guide, the further and more tiring the travel, the longer you'll want to stay to make it count. For a few nights, somewhere closer and simpler often beats a far-flung dream that leaves you jet-lagged and rushing.

4. Be honest about budget

Destinations vary enormously in day-to-day cost, and a "cheaper" flight to a pricey city can cost more overall than a slightly dearer flight somewhere gentle on the wallet. Think in terms of the whole trip — getting there, staying, eating and doing — and let your comfortable number guide the shortlist rather than stretching to a place that'll have you counting pennies.

5. Check the practicalities early

Nothing deflates a great idea like discovering a visa you can't get in time. Before you fall in love, do a quick reality check: passport validity, visa or entry requirements, any health or vaccination considerations, and the current official travel advice for the area. These rarely change the destination — but they do change when and how you go.

6. Make the choice — and commit

At some point, more research stops helping. When two or three options all excite you, you've already won; pick the one that best fits your season, budget and time, and pour your energy into making it brilliant. A well-planned "good" choice beats an endlessly deliberated "perfect" one.

The short version