✈️ Plan A Whole Trip With AI (Without The Overwhelm)

Type “plan me a week in Portugal” and you get a brochure. Day 3: explore the charming old town. Day 5: sample the local cuisine. Every travel blog on the internet, blended to paste.

That’s what a request with no information in it deserves.

I run my business from a laptop in South Thailand, so take my word for it: the first thing to tell Claude about a trip is who’s coming and what the real limits are.

Three prompts, in order, same chat.

1. Constraints before countries

Nick this one, fill in the blanks:

You're helping me plan a trip, fitted to my actual party rather than an imaginary one. Don't suggest a single destination yet.

Here's the unglamorous truth:
- Budget: [amount] per person, [including / not including] flights
- Dates: [dates], flexibility: [none / a few days either side / whole month open]
- Travelling from: [airport or city]
- Who's coming, honestly: [e.g. "Sam: happy anywhere, hates early starts. Mum: nervous traveller, over-packs, much calmer when she knows the arrival plan"]
- Energy: [flop / march about / a negotiated settlement between the two, roughly this ratio]
- Non-negotiables: [e.g. "somewhere warm", "one flight maximum", "decent veggie food"]
- Things we say we'll do and never do: [e.g. "we claim to like hiking, we do one hike"]

Now:
1. Play the constraints back to me in five lines, so I can see what you think I said.
2. Tell me which of them pull against each other, if any.
3. Ask me anything important I've missed, then wait. No destinations yet.

Rules: no brochure language, no "charming old towns". If something I've written is vague, say so instead of filling the gap yourself.

Ask me up to three questions before you start.

The bit people skip: the character notes. A budget is easy to plan around. A friend who needs quiet mornings, or gets anxious without a plan, is what shapes a good trip, and Claude handles “one of us hates surprises” beautifully once you say it out loud.

2. Three options, with the catch attached

Then this:

Now give me exactly three destinations that fit those constraints. Three, not ten.

For each one:
1. Why it suits this group, referring back to what I told you about them.
2. A rough cost sense against our budget, flights in or out as I said.
3. What the weather's doing during our dates.
4. The catch. Every option has one, so tell me rather than sell to me.
5. Which you'd pick for us, and what would have to change for a different one to win.
6. Then build the comparison as a downloadable spreadsheet, one row per destination, for the group chat.

Rules: use web search for anything seasonal or timetabled, and mark clearly which details I need to verify myself before booking. Don't invent prices. If none of the three are strong, say so rather than pad the list.

Ask me anything you need to know first.

Then haggle. “Option two but in September?” “What would it look like with £200 more each?” “None of these grab us, go weirder.”

Why three and never ten: ask for ten and you’ve rebuilt the 47-tab problem inside a chat window. Three is something you can put to a group chat without starting a war.

3. The boring bits

Same chat, so it already knows the destination, dates and who’s coming.

And this:

We've picked [destination]. Now the admin, in three parts:

1. A packing list for this group, this place, these dates. Grouped by person where it matters, with a firm "you will not need this" section for whoever over-packs.
2. A before-we-go checklist: passports, insurance, adaptors, roaming, cards that work abroad, booking confirmations, anything country-specific like visas or entry forms. Flag which ones I must check on an official government page rather than take your word for.
3. A day-one plan, landing to bedtime, assuming everyone's tired and nobody has data. Gentle and specific: how we reach the accommodation, a low-effort dinner nearby, nothing else scheduled.
4. Then give me all three as one document I can download and print.

Rules: specific to our dates and this group, never generic. "The evenings drop to 12 degrees, pack one warm layer" is useful. "Pack clothes" is not.

Check with me before you guess.

The day-one plan is the highest-value thing nobody asks for. Day one is when everyone’s tired, nobody has currency or a SIM, and the mood for the week gets set.

What one honest line does

Write “Mum: nervous traveller, will pack six cardigans for a heatwave” into prompt one, then watch it work downstream. The shortlist skews towards direct flights and short transfers. The packing list turns up with a kind “you will not need this” section you can hand over with a grin. The day-one plan is detailed enough to send to the group chat three days early, which for a nervous traveller beats a sea view.

You didn’t design any of that. The constraint did.

The catch

It can’t book anything, and it shouldn’t. Prices and timetables change constantly, so treat it all as a strong first draft and verify before money leaves your account. Building files also uses your free allowance faster than chatting, so if it asks you to come back later, nothing’s broken.

Visas get special caution. Let Claude flag what to look into, then read the official government page yourself, because “the AI said I didn’t need one” is not a sentence you want to say at a border.

And it can’t fix group dynamics. If one of you wants ruins and one wants a lounger, it’ll engineer a clever compromise, but somebody still has to say it out loud over dinner.

Tonight

Send prompt one for whatever trip is vaguely on the horizon, even the “we should do something at Easter” one that’s currently just a feeling. Getting the constraints out of your head is where a trip stops being a cloud and becomes a plan.

Happy travels. For the pile that grows while you’re away, The 10 Prompts That Do Your Admin is waiting when you land.