If you’re already scrolling through destinations, hotels and flight prices, stop for a moment.
Before you choose where to go, there are seven important questions worth asking yourself first.
A good travel advisor will ask them. If you’re booking independently, you should too.
Why Most People Miss Out on Choosing a Better Holiday
If you’ve ever come home from a holiday feeling slightly underwhelmed, despite spending a small fortune on it, there’s a good chance the problem wasn’t the destination.
It was the decision-making.
Most people start by asking: “Where do I want to go?”
Then they disappear down an internet rabbit hole of destinations, hotels, reviews and special offers until eventually they book something that feels familiar enough to be safe.
The trouble is, familiar isn’t always what you really want. And if you keep booking the same sort of holiday and feeling disappointed by the result, at some point that’s on you.
Not because you’ve chosen badly. Because you’ve skipped the thinking.
Before you book anything, ask yourself these six questions.
1. What has been my favourite holiday?
Not the most expensive trip. Not the most luxurious. Not the one that looks best on Instagram.
Your favourite.
Then think about the aspects that actually made it special.
- Was it watching the sun come up over the Namib Desert?
- The conversations you had with strangers you met on a tour?
- The feeling of achievement after completing a long hike up a mountain?
- The freedom of having nowhere particular to be?
Until you understand why you loved that trip, you’re largely guessing what might make the next one special too.
2. What do I want this holiday to do for me?
This is the question most people never think to ask.
You’re probably focusing on where to go.
Instead, ask yourself what you really need. And how you want the experience to make you feel.
- Do you need rest?
- Adventure?
- Connection?
- Time with your partner?
- A challenge?
- To celebrate something?
- To prove to yourself you can still do something you’ve always dreamed about?
A destination is just a location.
What matters is how you want to feel while you’re there and when you come home.
3. How do I actually like to travel?
Not how you think you should travel.
How you genuinely enjoy travelling.
- Do you love every detail being organised for you?
- Or do you prefer making it up as you go along?
- Do you enjoy moving, waking up in a new place every day, or just staying in one place?
- Do you love walking, wildlife, food, trains, history or meeting local people?
Be honest.
There is no point booking an adventure-packed itinerary because it sounds exciting if what you really want is a week with a good book and a sea view. Or booking a luxurious hotel and then feeling bored because it feels polished rather than authentic.
4. What are the practical realities?
The holiday doesn’t start at the airport. It starts when you shut your front door.
If you live in Cornwall (as I do) that might mean a six-hour journey before you’ve even reached the airport, (assuming there are no delays) let alone the time allowed for checking in.
An early morning flight might require an overnight hotel. A cheaper airport might actually cost you more in time, stress and parking.
Don’t ignore the logistics. And these can be the greatest headache of all.
A holiday that looks perfect online can feel very different at four o’clock in the morning when you’re dragging a suitcase across a car park.
5. What are my non-negotiables?
What would make you genuinely unhappy if it wasn’t included?
- A direct flight?
- A balcony?
- A single room?
- A swimming pool?
- Good food?
- A small group?
- Walkable restaurants?
Don’t be embarrassed by your answers.
Your holiday isn’t being marked by an examiner.
The more honest you are about your non-negotiables, the more likely you are to choose something you’ll genuinely enjoy.
6. What do I want to be talking about when I get home?
This is my favourite question.
Imagine you’re sitting with friends a month after your holiday.
- Are you talking about seeing elephants crossing the road in front of your safari vehicle?
- Swimming in crystal-clear water?
- Walking through mountain villages?
- Learning to cook local food?
- Travelling by train through spectacular scenery?
- Or are you mainly talking about the hotel breakfast?
Because the answer often tells you exactly what kind of holiday you’re really looking for.
7. What Am I Prepared To Spend To Get The Holiday I Really Want?
You’ll notice I’ve left budget until last.
That’s deliberate.
Most travel advisors will ask your budget first. And that’s perfectly reasonable. It helps them understand what type of holiday they can realistically recommend.
But if you’re planning your own holiday, I think budget is a question for later.
Because before you decide what you’re prepared to spend, you need to understand what you’re actually trying to buy.
If what you really want is to relax by a pool in the sunshine, there may be dozens of ways to achieve that.
If what you really want is to see the Northern Lights, travel across Canada by rail, go on safari, or walk part of the Camino, that’s a different conversation altogether.
There’s also a difference between what you’d like to spend and what you’d be prepared to spend.
You might tell yourself your budget is £2,000.
But if you’ve always dreamed of seeing gorillas in Rwanda, cruising through the Norwegian fjords, or taking your family on a once-in-a-lifetime trip, you may decide that spending more is worth it.
Equally, you might discover that the holiday you really want costs less than you’d expected.
The point is this:
Budget matters. Of course it does. But it should support your decision, not make it for you.
Work out what you want first. Then decide how much you’re prepared to invest in making it happen.
Before You Open Another Browser Tab…
Make sure you’ve asked yourself these seven questions first.
Because if you don’t, you’ll probably do what most people do.
- You’ll choose somewhere familiar.
- You’ll choose something safe.
- You’ll choose what you’ve always chosen.
- And then, if it turns out to be merely “quite nice”, you shouldn’t be too surprised.
The destination matters.
But understanding what you want from your time away matters far more.
That’s why a good travel advisor starts with questions rather than destinations. So maybe it’s time to book a chat?
Because if you don’t know what you’re looking for, how will you recognise the right holiday when you find it?
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