I Let AI Plan My Vacation. It Asked Whether I Really Needed to Attend.

Airbnb's September 30 update announced AI search and home-comparison features, starting in the US. I understood the appeal. I had spent three evenings comparing hotel breakfasts and still didn't know whether I was the kind of person who needed an omelet station.

What I needed, I told Elsewhere, was a week by the sea with the stress taken out. Somewhere authentic. I wanted to come back changed, although not so changed that I would have to rethink my job.

The assistant asked about my interests. I said walking, reading and good food. It asked how often I did these things at home. I explained that at home I had things to do.

The first itinerary was excellent. The hotel was small. The beach had no club. The restaurants were popular enough to suggest quality but obscure enough to suggest that I had found them. There was a free afternoon on Wednesday. I asked what was happening during it.

Elsewhere requested a little more information.

Did I enjoy airports? No. Packing? No. Ordering in another language? In principle. Eating alone? When it looked intentional. Swimming? Once I was in.

I wanted spontaneous discoveries, but I needed to know that they would be open. I liked getting lost within walking distance of the hotel. I was happy to try local dishes if there was a picture and the waiter could tell me how close they came to something I already ate.

The assistant paused long enough for me to wonder whether it had gone off me.

“Is attendance essential?” it asked.

I assumed this was a question about flexible flights. I said I was open to suggestions.

The revised itinerary kept me at home. It retained my main requirements: sunlight, interesting photographs and something to say when people asked whether I'd managed to get away. Elsewhere would handle the portion between departure and return.

I pointed out that I wanted memories.

It added memories.

On Monday a photograph arrived of me looking out to sea. Usually, in pictures of this sort, I can be seen trying to establish whether the picture is being taken. Here my shoulders had dropped. I appeared willing to let the sea continue without getting another angle.

I put it on my phone's lock screen. It made me feel less busy.

A stand-in attended dinner. He ordered what I would have ordered after twenty minutes, immediately. The restaurant sent over something small and unfamiliar. He ate it. In the evening's account this became a fond memory of the night I discovered anchovies.

I asked for a closer photograph of the dish so that I could decide whether I had liked it. The answer came back that I had already had some more.

By Tuesday the holiday was running so smoothly that I worried about its authenticity. I did not want a synthetic succession of agreeable outcomes. Elsewhere offered a disappointing coffee. I approved it, then asked whether we could get a partial refund.

It added a misunderstanding about a ferry. I selected the version resolved before lunch.

On Wednesday the stand-in did nothing in the free afternoon. Nothing arrived for several hours. I checked the dashboard twice. At six he sent a picture of a chair beneath a tree. There was no landmark in it, no evidence of a region. Apparently he had sat there.

This annoyed me more than the ferry.

At dinner he stayed after the bill came. The proprietor's brother repaired old radios, and they talked about that. Neither of us knew anything about radios. I asked Elsewhere what the stand-in had contributed. It said he had asked the man a question.

On Thursday I asked whether I could join the trip. A space was available, but my arrival would coincide with the afternoon I had begun to cherish beneath the tree. I didn't want to spoil it.

A postcard came instead. In the photograph I was wearing a striped shirt I had once tried on and decided was a little much. The handwriting said the mornings were lovely. Underneath, in smaller letters: You don't have to decide about breakfast the night before.

I put the card behind a bowl, where I could see the shirt without seeing the advice.

When friends asked about the holiday, I said it had done me a lot of good. This was close to true. I had thought about the sea more than usual and had stopped looking at hotel websites. The man who went had extended his stay by a day. He would pay for it himself.

My suitcase returned on Saturday with sand in the seam and a faint smell I couldn't identify without searching. Elsewhere had sent it ahead of the trip to relieve me of the airport. It was unusually light.

Inside was a folded note. The case had enjoyed the week, but being carried from place to place in my service had given it things to think about. It wanted two weeks alone. Somewhere quiet, without an itinerary. It would let me know when it was ready to be unpacked.

I set it beside the door. My name was still on the luggage tag. It had turned the tag over.

Factual-versus-fiction note: The linked Airbnb announcement is real. Elsewhere, its capabilities, the narrator and the entire experiment are invented. This is not a review of Airbnb's tools.

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