Travel

Why I Stopped Chasing 'Big' Holidays and Started Booking Weekends Away

15 June 2026 5 min read
A quiet English village inn in golden afternoon light

For years I thought travel had to be a Big Event. Two weeks off, a long-haul flight, an itinerary with restaurants I'd screenshot months in advance. Then I ran out of annual leave, booked a Friday-to-Sunday somewhere two hours from home, and realised I'd had the maths wrong the whole time.

The problem with the big trip

A two-week holiday is a lot of pressure for one week to carry. You've saved for months. You've told everyone. By day four you're anxious about how fast it's going, by day nine you're running out of energy, and by the flight home you're already planning the next escape.

A weekend is different. It's small enough that nothing has to go perfectly. You show up, you walk somewhere new, you eat two nice meals, and you come home before the fantasy of it collapses.

What a weekend actually gives you

  • A genuine reset without the annual-leave guilt
  • Something to look forward to every four to six weeks, not once a year
  • Space to try somewhere you'd never fly to properly — a Dorset inn, a Norfolk beach, a Yorkshire market town
  • The joy of coming home to your own bed on a Sunday night

How I plan them now

I keep a running note on my phone of places I've read about, walked past, or seen someone else post from. When a free weekend appears, I book the first one that's still available. No spreadsheet, no group vote, no waiting for the stars to align.

The best trip I took last year cost me a train ticket and one night in a pub with four rooms. I still think about the walk we did before breakfast.

You don't need a bigger trip. You need a smaller life you don't want to escape from — and enough weekends away to keep remembering it.

You don't need a bigger trip. You need a smaller life you don't want to escape from — and enough weekends away to keep remembering it.

Want to see how I put this into practice? Take a look at my services or get in touch to talk through a project.

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