I Just Talked to It All Week: Using AI on an Actual Holiday

We walked out of a restaurant in Paralimni, still arguing about whether the fish was worth it, and I pressed one button and said out loud: dinner, cash, this much. That was it. By the time we reached the car it was a line in my spending log, in the right day, in the right category.

No app. No form. No sitting down that evening to “do the receipts”, which is a thing I have never once actually done on a holiday.

Nine days of that. I want to write down the small stuff, because the small stuff is where it stopped being a gadget and started being genuinely, stupidly convenient.

Standing outside the rental shop

There is a tiny hire place near the hotel. Three cars, four quads, a couple of buggies. I wanted one for the last days and I know exactly how those conversations go, so I stood on the pavement and asked, out loud: what do I need to ask these people so I do not cry about it later.

What came back was a checklist I could actually hold in my head. Price per 24 hours or until the return hour. Is the damage cover in the price or on top. What is the excess, that is the one number to write down. Deposit, cash or card block, and when do you get it back. Fuel full-to-full, because the “we give it full, you bring it back empty” version is a shakedown. Second driver written into the contract - an unlisted driver at the wheel means no insurance at all, not reduced insurance, none. And a straight question to ask them: does the cover include tyres, glass, underbody and roof, because nine times out of ten it does not, and on Cypriot roads those are exactly what breaks.

Then the bit I would not have worked out myself. They offered the zero-excess upgrade, and the answer was: do not buy it. Take the basic cover with the excess, because my own card already refunds an excess up to a limit well above theirs. It knew that because my card’s terms were already sitting in my own records, along with everything else. So the upsell that sounds like peace of mind was just money.

I read their offer back by voice from the pavement - automatic only, four-day minimum, this excess - and got it checked in about a minute: rate roughly half what the tour operator wanted for the same four days, excess fully inside my card’s cover, and their “minimum four days” happened to be exactly the days I had left before the flight, so the minimum cost me nothing.

Two minutes of talking, standing in the sun, and the whole thing was decided.

Things a German driver needs told once

Cyprus drives on the left. I knew that. What I did not know, and got told in one line: at roundabouts you give way to the right, which is the opposite reflex to the one my hands have. Rental cars carry red plates, so everybody on the island can see exactly what you are. Some of the mountain tracks void your cover the moment you turn onto them.

Also: film the car before you drive it. All four sides, roof, wheels, windscreen, bumpers from underneath, the interior, the odometer, the fuel gauge. Any scratch not marked on the handover sheet becomes yours on return. Five minutes, and it turns the whole rental from a leap of faith into paperwork.

None of that is exotic knowledge. But nobody hands it to you at the counter, and I had it before I walked in.

The parking thing

This is the one I actually enjoyed.

We wanted a day in the mountains, so first it built the route out of the interesting places - waterfall, mountain village, the trout farm, a monastery. Fine. Standard.

Then I said: now do it again, but find me the car park next to each one, put the car park in the route instead of the sight, and tell me how far I walk from each.

And it just did it. Coordinates for where the car actually goes. Monastery 130 metres from that car park. Village square 39 metres from another. The waterfall its own point higher up. Plus the thing you only learn by asking: the old village centre is cobbled and pedestrian, do not drive onto the stones, the free asphalt parking sits eighty metres short of it.

And then the part that actually made me laugh: it came back as links. Not a description of a route, not “head south on the B3” - an actual navigation link per stop, plus one for the walk from the car park to the thing. I tapped it, Google Maps opened with the destination already set, and I drove.

That is the step everybody skips when they talk about this. A plan you have to retype into your phone is not a plan, it is homework. I typed nothing. Nine days, and I did not once assemble a route by hand.

A list of sights is a wish. A list of car parks with walking distances, each one a link you tap, is a day you can actually execute at two in the afternoon in 34 degrees with someone asking where we are going next.

It also priced every leg: 5 km to the post office, 149,7 km and 2 h 20 to the trout farm, 17,6 km and 24 minutes down the southern slope, 157,5 km and 2 h 19 home. 338 km and 5 h 25 behind the wheel for the whole loop.

And the post office was an errand I could not skip, sitting in the wrong direction. I asked what the detour cost. 0,8 kilometres, one minute. That is when I stopped negotiating with myself about it.

“2 h 20” and “a couple of hours” build different days. With real leg times you stop cramming four stops into a day that fits two.

The small questions, all week

Not “what should I see in Cyprus”. These, ten times a day, out loud, mid-walk:

• Shut on Mondays?
• Is 34 at the coast also 34 up the mountain, or 24 with wind? Changes what everyone packs.
• Which fuel grade does the contract require, and is it the cheap one?
• If we cross to the north of the island, what stops working? Answer, about a hundred metres past the crossing: my maps went blank. Good to know before you need them for the way back.

Thirty seconds each. Not one of them clever. The whole point is that asking got so cheap I asked instead of guessing, and a week of not guessing feels completely different from a week of guessing.

And then the railway tried it on

On the way out, our train to Berlin got swapped - same departure, different set - so our reserved seats went with a train that no longer existed. I claimed the reservation fee. Refused: delay at the destination was three minutes, and compensation needs sixty.

True, and beside the point. So I had the actual conditions of carriage read, in the edition in force on our travel date, not the current one. Clause 5.4 grants that refund on three separate grounds and only the third one mentions delay. Ours is the second: seats allocated, then not held. Their own claim form even walks you through “delay under 60 minutes” and then “I could not use my reservation” - so they provide for this exact case and answer as if they do not.

Then the German letter, clause quoted word for word, escalation body named, deadline set. My whole job was to read it and press send.

I would not have opened that PDF. Nobody opens that PDF. That is the point.

Afterwards, the bit that surprised me

One line in my log had no date on it. A boat, a whole afternoon on the water, and nowhere any note of which day it was.

I did not remember harder. I asked 639 photographs when they were taken, and one cluster answered: 15 August, 17:47 to 19:11, ninety-six frames on the water. Entry dated, from pictures.

Same pass checked a distance I had quoted from memory, two independent ways, and it held. And every place we actually went is now in my own database with a verdict attached - where to park, worth it or not, what never to order again. Next August the first question does not go to a search engine. It goes to me, written down while it was fresh.

Where it still needed me

Three, honestly, because a week of only wins is an advert.

The first route map it drew spanned Europe and titled itself with two cities we had never set foot in - their coordinates came from photographs taken out of a plane window. Nothing was broken. Every step did what it was told, and the output was a confident, well-typeset lie. I caught it by looking at the picture.

The photo ranking gave a perfect score to two different frames of the same building and could not tell me which was better. It gave the same perfect score to a rotated snapshot of a car park.

And one draft had me saying a meal was worth every cent. I never said that. It filled the sentence in because it made the paragraph land better. A wrong map is obvious. An invented opinion in your own voice is not.

What it actually felt like

Nothing on that list is impressive on its own. Parking coordinates. Opening hours. An excess I did not need to insure twice. A clause number from the right edition. A dinner logged by talking while walking to the car.

Put together, though, a whole week ran without the usual friction. No evening spent on receipts. No standing at a rental counter being sold something. No arriving somewhere lovely and circling for parking. No shrugging at a refusal letter because reading the terms is more effort than the money is worth.

The decisions stayed mine the entire time - where to go, what to skip, whether to fight over a reservation fee. It just took the arithmetic and the small print off my hands, and I got to be on holiday instead of managing one.