“We walked here from Praiano,” we told the delightful young woman at the front desk of the Furore Grand Hotel. That’s all it took for her to burst out laughing.

Four Americans had come in from the hillside rather than up the driveway, which is apparently not how guests typically arrive. We were sunburned, scratched, and spent. Heat stroke hadn’t arrived, but it was clearly in the neighborhood. Liz’s chin had the same flush it had in Moab last May, and I have learned to read Liz’s chin the way sailors read the sky. We asked whether the hotel might spare some water. She said of course, and asked what kind.

All four of us answered at once, a bit breathy but certain.

“Still, not sparkling.”

Even near collapse, we knew what we liked. Our new front-desk friend kept laughing while I explained exactly where we’d been, and laughed harder when I told her how long it had taken. She was still composing herself as she showed us to chairs by the pool and set down menus.

If you read my recent essay, “The Distillery,” you know how this trip started. I sent my friends Karen and Marty eleven pages about a vacation, and the response was about as warm as you’d expect. I promised in writing to stop disguising my use of AI. My fake mustache, I announced, was coming off.

Then we got to Italy.

Three of the four of us had one request for our first free day in Praiano. They wanted the day calm and unplanned. Our travel planner, Ashley, had suggested something more ambitious, but she accepted the group’s decision. I accepted it too, in the sense that I agreed out loud and then went off and planned it.

Before anyone else was up, I got on my phone and asked Claude how to make the most of a day with nothing scheduled. It gave me a lovely answer. I trimmed it, the way I trim everything, and sent the result to the group thread.

From a friend:
Head to Fiordo di Furore for a swim. It’s a tiny beach at the bottom of a gorge under the big bridge, just past Praiano. The sun only hits it from about 11 to 2:30, so we’d leave around 10:45. It’s 200 steps down, no facilities, so bring water shoes, towels, water.
After that, hop over to Amalfi for a late seafood lunch and a wander around the cathedral and back lanes, then back here by 5:30 for sunset at San Gennaro and dinner in Praiano. Easy night before driver day.

That is what an unplanned day looks like when I’m in charge of not being in charge. It had a departure time, a gear list, a cathedral, and a sunset. I had scheduled the sun.

Liz has long since learned that “From a friend” means Claude. Karen and Marty assumed I had friends.

“Just past Praiano” sounded unequivocally walkable to me, so we walked, dressed as instructed for the beach. I had told everyone the climb back up would be a gentle warm-up for Wednesday’s Path of the Gods hike. The beach was supposed to be forty minutes away.

Praiano marks its footpaths with little ceramic fish, and for the first stretch they were everywhere. It felt like being guided by the town itself. We were charmed. We commented on the fish. Then the fish thinned out, which in hindsight was the town quietly withdrawing its endorsement. The path got rougher.

At one point I had the distinct feeling that something was wrong, so I pulled up the route on Apple Maps. There was the blue line, calmly assuring me we were exactly where we should be. I spent years at Apple helping people trust what’s on the screen. It didn’t seem like the moment to stop.

The blue line stayed confident. The time estimates did not. They kept getting longer instead of shorter, which is not the direction you want time estimates to go. Several times the trail split into two faint suggestions, and we chose one by informal vote, then came back and tried the other.

Then a thicket of something with very sharp opinions caught Liz’s beach cover-up, the flowing cape kind that nobody designs with bushwhacking in mind. She was momentarily trapped. I knew right then that we were in trouble. Actually, I knew that I was in trouble. I spent a careful few minutes freeing Liz, although the thorns had already done some damage. From that point on, the hike had a soundtrack.

“Oh, Rob.”

The first one was almost affectionate. By the second hour, it had acquired an edge, and by the end, it was a complete sentence with a verdict. Later versions were more colorful. I’ll spare you.

Somewhere in that second hour, I mentioned what my friend had said about the beach, and then, helpfully, that my friend was Claude. I genuinely thought everyone knew. Liz knew, and I had assumed Liz was representative. My real friends, after all, have names.

It took two and a half hours. We never reached the fjord. Somewhere below us, the sun was hitting the beach between 11 and 2:30. I had scheduled it, and I assume it kept the appointment. We came out instead at the Furore Grand Hotel, which is how I ended up standing at the front desk negotiating water.

The hotel was gorgeous. The pool looked out over the coast, the Aperol Spritzes were cold, and the caprese was the kind that makes you quietly reconsider every tomato you’ve eaten at home. I would happily have discussed those tomatoes for an hour. Nobody at the table wanted to discuss how we got there.

Mentioning AI was off the table. That had been clear since my announcement on the trail. So I excused myself to the hotel bathroom, locked the door, and reread what my friend had actually said.

There it was, one sentence. Take a taxi or the SITA bus toward Amalfi, get off at the Furore Fiordo stop on the bridge, and walk about 200 steps down to the beach.

I had kept the steps and cut the ride to the steps.

I take real pride in making complicated things simple. I named a company after it. On the Amalfi Coast, I took a perfectly good plan and distilled the bus out. It was, I have to say, a very clean edit.

Worse, I’d done the editing quickly and alone, then handed the result to three people who had no reason to question it. Advice from a friend doesn’t come with a revision history. Nobody asks to see the original.

Back at the table, I tried to bring it up. I had found the original instructions, I explained, and they were quite clear. The machine had recommended a taxi or a bus. The machine had not recommended a two-and-a-half-hour trek through the Italian wilderness.

“Too soon,” said the table.

I had evidence. I had the original transcript. I was prepared to stipulate that mistakes had been made, but I thought the distinction between the machine’s recommendation and my execution deserved some consideration.

Nobody was interested in the distinction.

It took Karen the longest to sort out, and I’d have bet on her taking it best. Karen used to work at Google. She uses Gemini all the time. She was the last person on that hillside who would hold a chatbot against me. What she held against me was the word “friend.”

She had been handed a plan she thought came from a person, and when it went wrong, she had to work backward to figure out which parts to be angry about. Eventually she got there. Go to the fjord was Claude’s idea, and it was a good one. Hike through the wilderness to get there was Rob’s.

“From a friend” was never meant to fool anyone. It was a private joke, and I’d forgotten it was private. I had promised to take the mustache off, and it turns out I’d worn it so long I couldn’t feel it anymore. Had I written “From Claude” at the top of the text, someone might have asked the obvious question about how we were getting there.

Instead, I’d been happy to take credit for a lovely plan until it went wrong. Then I wanted everyone to know which parts weren’t my fault.

I made one more attempt. I pointed at the view, the pool, the menus, and the woman at the front desk who was still laughing. None of this was on any plan, I said. Here we were, enjoying the very spontaneity everyone had requested in the first place. I paid homage to serendipity.

Marty, I should mention, once sent me a text about his love of serendipity on vacation. I thought I had a strong argument, possibly even an ally. He did not bite. Nobody bit.

That’s when it became my turn to be annoyed. I had been wrong about the taxi and right about the hotel, and I could already see which of the two would be the topic of discussion for the rest of the week.

I was in the doghouse for days. We did see the fjord eventually, from a boat, two days later. Claude was right. It was worth the trip.

The woman at the front desk, I’m sure, still tells the story. Four Americans simply came out of the hills one afternoon asking for water, and they were very specific about the kind.

Stubbornly Human is a newsletter of essays about what stays ours as machines get better at being us. A new essay arrives every other Monday. Subscribe at stubbornlyhuman.ai. It’s free, and I write it myself. Mostly.

From a Friend