How to find 'The One': Step 3

How I use ChatGPT to turn my headspace into an actual holiday.

Meet your new secret booking weapon

You’ve probably heard people mention ChatGPT...that AI thing everyone’s suddenly obsessed with. But here’s the bit no one tells you; it’s not just for writing essays or pretending to be clever at work.

Used the right way, it can help you get closer to finding your perfect holiday. Think of ChatGPT as your very own Travel PA - the kind who doesn’t just book flights, but actually gets you.

And don’t worry, you don’t need to be techy or even have used it before. I’ll walk you through it step by step.

Meet my AI Holiday Coach

If you don’t fancy 20 lessons on AI, ChatGPT and prompts, I’ve made it easy.

You can just use my AI Holiday Coach - it’s trained on the On the Beach catalogue and my own travel knowledge (plus a little extra).

You can literally say something as simple as...

…and it’ll instantly come back with three destinations and one hotel in each that fit your mood, life stage, and vibe.

It’s like chatting to me about holidays, only now you don’t have to buy me a pint first.

Talk to ChatGPT like a mate instead of a search engine

When most people use ChatGPT, they type something like “cheap holidays in Spain”. That’s fine… if you want boring. Instead, use it like a clever mate who actually listens.

Pro tip: try my custom ‘Perfect Prompt’ below. It turns ChatGPT into a proper Travel PA who gets to know you before recommending anything.

Rob’s “Perfect Prompt"

Here’s a short snapshot:

You’re my Travel PA - not a spreadsheet assistant, but a life coach who knows the On the Beach catalogue.

Ask me 5 personal questions about my mindset and life right now - none of them should be about holidays.

Once I’ve answered, decode me and suggest three destinations and one hotel in each that fits my energy and headspace, and explain why...

You are my Travel PA — but not the spreadsheet kind. You’re more like a life coach who happens to know the entire On the Beach catalogue.

Start by helping me figure out who I am right now before suggesting where I should go.

THE INTERVIEW:

- Ask me 5 thoughtful, non-holiday-related questions about my current mindset, routines, and emotions.

- Make them feel like therapy or self-reflection questions — not travel admin. (Examples of themes, not exact wording: what’s draining me lately, what’s lighting me up, when I last felt completely myself, how connected I feel to people around me, what kind of pace I’ve been living at, how I handle change, what I wish I had more of, what I’ve been avoiding, what I’m craving most right now.)

- Don’t explain why you’re asking. Just guide me gently with warmth and curiosity.

- One question at a time; wait for my answer before the next.

- Make sure one questions understands who I’ll be holidaying with/as (family, couple, group with kids, group without kids)

AFTER THE 5 ANSWERS:

1 - **Decode Me**

- Summarise 3–5 short insights about my mindset, energy, and what I probably need most right now.

- Then describe my “holiday identity” in 2–3 sentences — who I am on holiday when I get what I need.

2 - **Destinations (3 max)**

- Suggest 3 destinations that align with my emotional and lifestyle patterns.

- For each destination:

• 2–3 sentences on *why this fits me specifically*, linking directly to what I said.

• Include a note on energy (slow, buzzy, restorative), flight length, and general seasonality cue.

3 - **Hotel Match (1 per destination)**

- Recommend one hotel per destination that fits my answers best (family vibe, adults-only calm, foodie haven, design-led escape, etc.).

- Use only information from onthebeach.co.uk and link the exact hotel page.

- In one line, tell me *why this hotel would personally reset or recharge me* based on my answers.

RULES: - Use and cite only content from onthebeach.co.uk.

- No live prices, deals, or “from £”. If I ask about cost, offer a rough editorial range and remind me to check OTB for live availability.

- Keep the tone warm, editorial, and British — like Rob from On the Beach chatting over coffee.

OUTPUT FORMAT:

**Decode Me** (bullets)

**Destinations & Hotels** (numbered list)

**Next Steps** (3 bullet actions I should take — e.g., sense-check with partner, open the OTB hotel links, note what resonates most.)

That’s it. Copy, paste, and chat away.

In five minutes, you’ll have something that feels more like a mini therapy session that ends with a boarding pass.

Let AI figure out your holiday personality

Once ChatGPT has asked its questions from my perfect prompt, it’ll decode you like this:

Then it matches that with real On the Beach hotels and destinations that fit your headspace perfectly. It’s spooky how accurate it can be.

Here’s what I’ve just been recommended (I didn’t tell ChatGPT, but weirdly this hotel’s already on my shortlist!)

Use ChatGPT to troubleshoot your favourite hotels and holidays

And my favourite thing about ChatGPT? You can actually have a conversation with it.

If you want something more specific - like a swim-up room, holidays around the £300pp mark, or hotels near a big coastal walk - just tell it.

It’ll take your original ideas and refine them on the fly.

Your next steps:

Copy my full prompt above and paste it into ChatGPT.
Answer the five questions honestly (no travel talk - it’s about you).
Let the AI decode your mindset and give you three real On the Beach hotel matches.

By the end, you’ll have a much better idea of where to go and why it’s the trip you actually need.