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Holidays and AI

By Theodora Taylor Franks on 9th June, 2025

Holidays and AI – are we all about to be out of jobs?

One of the many things that worries me about AI, both in the small travel-industry niche and in the wider picture, is synthetic data.

Or – as I like to call it on slightly bleaker days – AI cannibalism. AI using content created by AI to make .. yet more AI content – which is then published on the internet, and so on.

At some point, reality drops so far out of the mix that you’re left with a strange mish-mash of information that isn’t quite right, is very generic, and gets harder and harder to sense check…

Scary!

So. The big question then. Do we use AI at Fleewinter to help plan holidays?

Use of AI at Fleewinter

TL;DR: we don’t use AI to plan your holidays.

AI is an incredible tool.

There isn’t a day where I don’t use GPT, Gemini or Claude – I like different models for different tasks.

In my day to day, I use it to find images fast. I use it to analyse feedback; to give me ideas for content that travellers are searching for (sadly my job is more tactics than Thailand-holiday planning!) – and generally to use a very smart machine for a lot of processes that used to take hours of manual work.

That frees up more time for me to do the bits of my job that a machine can’t. I can’t use AI for chatting to the team, or creating personal relationships with suppliers and partners.

What we don’t use AI for?

That said, there’s a few non-negotiables – some tasks are sacred.

We don’t use AI for planning your trips & we don’t use it for giving recommendations and suggestions.

I often apply a simple rule – if I were my customer, and knew that something had been done with AI, would I be happy about it?

Where holiday planning is concerned, the answer is a definite no. Holiday planning is, and always will be, a human’s job at Fleewinter.

After all, our whole business model is that we plan your holidays, using our real knowledge and on the ground expertise, so that you don’t have to.

If we simply planned your holiday with AI, well then you might as well do it yourself.

Which leads us neatly to the question – is AI going to make Tour Operators redundant?

I’m pretty certain it’ll be a long time before AI takes over the human touch of bespoke holiday planning.

Human experiences are difficult to get into writing, and so difficult for LLMs to search or understand.

Experience is nuanced, sensory, and personal.

I don’t think a computer can replicate this yet. I don’t think that travellers will trust machines enough to spend thousands of pounds on, any time soon.

In short, I don’t think that AI will be a threat to human-planned holidays anytime soon.

But how we use AI in holidays matters.

If you ask ChatGPT to plan you a holiday, it’ll do just that. You’ll be presented with what it thinks will be the most acceptable trip (we asked Barbara to analyse a GPT itinerary last year!) – but it won’t touch the sides of what a human can do.

Which is why at Fleewinter, it’ll always be a real human planning your holiday. Meet our team here

 


Theodora Taylor Franks
Itineraries & Destinations