How to plan the perfect holiday

Buckle up for a post dedicated entirely to anti-productivity. I know; it’s unusual for the likes of me, when I’m usually so focused on maximising my own productivity. I mean, for God’s sake, I’ve got heaps and heaps of posts dedicated to just that: productivity tips, productivity vs procrastination, productive procrastination.

This is not going to be one of those posts. Lately, I’ve really been coming around to the idea that life is so much more about work. Should you try your best to find a job that you love? Absolutely. I love getting to teach every single working day; but it’s not my whole life. For 13 weeks of the year, I’m actually not at work. In fact, I’m writing this post on the train to see friends in Worcester, fully taking advantage of my time off.

Some people wouldn’t call that a holiday. In a normal office job, some people only take time off to go somewhere, whether it’s Wales, or Scotland, or Menorca (three places that I did visit this year!). Others advocate for time off to do literally nothing at all, which I’m actually a huge fan of too.

Either way, here’s how I’d go about planning the perfect holiday, according to what you want out of your time off. To figure that out, I’m going to use this space to answer three crucial questions. To skip ahead to the checklist for planning a perfect holiday, scroll all the way to the bottom of this page.

Why are you taking time off?

Have you booked yourself off work because you want to escape somewhere? If so, it’s time to start thinking about destinations and places to stay, either in this country or abroad.

Or have you taken time off to give yourself time to rest and recuperate? Maybe work has started to burn you out and you’re in desperate need of a ‘holiday’ at home. Use that time to catch up on chores you may have neglected, take a self-care day, watch movies all day or go for a nice walk.

Finally, you might be taking time off for an event. Is it a wedding? A party? Some other special occasion? Be sure to still leave time for yourself too, either in the morning or evening, to really get the most out of not being in an office for a day.

What do you want to do?

This is a really critical question. What do you want to do? If you’re staying somewhere other than your regular home, are you hoping to go exploring in a foreign land? Maybe there’s a gig in Edinburgh that you’re dying to attend, or a beach you have to visit in the Costa Del Sol.

Decide whether your holiday is going to be for relaxing or for adventuring. Do you want to get out everyday and see the sights or lounge by the pool under the sun? Use a spider diagram to brainstorm different ideas, and things you’d like to do or see. It might be a great opportunity to put together some sort of bucket list so that you can start ticking things off, otherwise you might never get to do the things you’ve always planned to.

Where do you want to be?

I mean this in every sense. Do you want to go abroad or stay in this country? Are you hunting sunshine and heat or does the weather not bother you?

How about accommodation? Which sounds better – a hotel with unlimited buffets and evening entertainment, or a villa with a private pool and the freedom to do what you want to?

Or should you save money on the living quarters and splurge on the experiences? Maybe a hostel would suit you best? Regardless, deciding on where you want to be could be a crucial step in planning the perfect holiday.

Your perfect holiday checklist

Screenshot this and circle each choice to show yourself what you’d like out of a perfect holiday:

  • Weather: Sunshine/snow/storms/no preference
  • Accommodation: hotel/villa/hostel/cottage/other
  • Location: abroad/local
  • Specific location: ______ (add your choice!)
  • Activities: adventure + explore/relax + unwind

What does your perfect holiday look like? Let me know your tips for planning it in the comments below.


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