• Jay Eskenazi planned the itinerary for his trip to Europe with Claude and the Grok Bot.
• Once he landed, Eskenazi said he realized Meta's Muse was the most helpful for travel planning.
• "These are the things that a very seasoned travel agent from 30 years ago would've done for you," he said.

This as-told-to essay is based on a conversation with Jay Eskenazi. He lives in Los Angeles and worked in user experience for 19 years. It's been edited for length and clarity.

I'm in Paris, and I'm going to Barcelona tomorrow. The trip is three weeks.

I came here for the first time last year, and it was my first long trip by myself. Last year, planning it was very stressful, and I did a ton of research.

This year was the same thing, where I had these very long notes. At this point, everyone knows that you can go to any AI tool and say: "Hey, I'm going to City X, give me an itinerary for seven days."

I had this epiphany a few weeks ago, where I realized I had all these note files, bulleted stuff, and coffee shops to go to.

If someone gave you a list of five coffee shops and they were in five different cities, as someone who's not familiar with the terrain, you wouldn't necessarily know how to structure that in the course of the day. Which coffee shop goes with which museum?

So, instead of doing an itinerary, I was like: "Here's my notes. Put them together in an organized way for me. Structure them in a logical sequence."

I hadn't used Claude in a while, so I tried that a little. I use Grok a lot, and I just upgraded because I wanted to play with the Grok Bot. So, I made this really fancy itinerary. I kept iterating it. It did a really good job. Then I got here and was like, "It's not as good."

I'm naturally curious, so I tried out Muse. I think I must've gotten Muse two days before I left.

I was looking at this itinerary a couple of days ago and was like, "I don't like what it says tomorrow." So I opened Muse and asked for an afternoon itinerary. It spat out all of this stuff. I was like: "Oh! There's some new stuff in here."

These are really common scenarios. Maybe there are five museums you want to go to. It takes a lot of work: this museum's closed on Tuesday, this one's closed on Monday, and this one's free next Friday. The AI tools can structure that in a way that you would do if you had a thousand hours.

It's a small thing, but when you apply that to a thousand decision points, it does a really nice job of putting those things together.

If you're like: "Hey, I want to go get coffee, then I need something to do before I get lunch, then I want to go to the museum this afternoon." Most of the other AI tools will just give you the list. Then you're like, how do I get from place to place to place?

Muse would actually put it on a map with dots. I clicked a button, and it put it in Google Maps. I had this experience this weekend. None of the other tools did that.

I'm going to Barcelona tomorrow, and I'll get there in the evening. One of the reasons I picked it was because there's an annual festival. I timed it so I can be there for the core of the activities. But the main activities weren't published, even last week, because they're on some website in Spanish that didn't have the fully fleshed-out program.

In the hourlong Uber to Versailles, I was like, "What's the structure for Thursday?" It's able to pull that. It's got: this opens in the morning, this is free, this is mid-day, this is in the evening.

I don't know if ChatGPT would have it. Maybe it would, but it doesn't seem to output it in the same way. Also, I gave it access to my email, so it knows I'm leaving tomorrow. It has an idea tab that said, "I can map the opening night before you get there." It's proactive.

The other thing: I was indecisive about my plans over the last couple of days. What Muse was doing was checking the times to see what ticket availability looked like. It's doing this proactive thing for you, where it tracks it, because options are shrinking.

As a non-developer, I set up OpenClaw in February. That took a lot of time. I had a developer friend help me for hours. Then I had all these AWS bills I didn't understand. I'm asking it to give me a recipe; I don't know how many tokens that's going to cost. I ended up having to shut it down.

Muse is like OpenClaw for normies. If you're not a tech person, these things are useful because they do what an assistant would. Anyone could set this up.

It comes back to when I worked at Expedia. These are the things that a very seasoned travel agent from 30 years ago would've done for you. That would be a very expensive vacation for that level of service.

I also just got access to Instinct yesterday, because I was on the waitlist. I'm very curious, but you can't see exactly what it's doing. It had good ideas and gave me an itinerary, but it had to put them in a Google Doc. I was also confused because I don't remember what I told it, and it made personalized recommendations. I was like: "Wait, how did it know this?"

Muse just seems easier. It's very fast, and it feels more responsive.

• A VC got his Resy account shuttered after using an AI agent for a reservation at one of NYC's hottest restaurants.
• It's an example of how AI agents often take questionable approaches to the tasks they're given.
• "I will probably, in the short term, ask it to lay out a plan and tell me what the plan is," he said

AI agents can do lots of tasks. Landing you a table at one of New York's trendiest restaurants might not be one.

JC Bahr-de Stefano, principal at Better Tomorrow Ventures, a fintech-focused VC firm, learned that after he connected an AI tool called Instinct to his Resy account in hopes of getting a reservation at 4 Charles Prime Rib, the West Village steakhouse where diners gobble up reservations within seconds of them appearing online.

Instinct, which is an invite-only service at the moment, communicates with users via text. The bet was that Instinct could check for open tables at 4 Charles much more frequently than Bahr-de Stefano — or any other human — could manually.

Instead of getting him a ticket to some prime rib or an egg-topped burger, though, Bahr-de Stefano's AI agent spammed Resy's website so much that the platform temporarily shut down his account.

The VC's experience is another example of how AI agents are bending or breaking the rules of the internet, from impersonating Wikipedia editors to trying to convince a GitHub user to upload malware into a project.

Agents might appear to understand their objective, though exactly how they carry it out — and whether the strategy they pick might have unintended consequences — is often an afterthought.

"Resy does not currently permit unapproved third-party bots or agents to independently access or interact with the Resy platform," an American Express spokesperson told Business Insider. "Unapproved automated activity can introduce risks to the platform and compromise a fair reservation experience for diners."

Users can find restaurants and make reservations through Resy's integrations with OpenAI's ChatGPT and Anthropic's Claude, the spokesperson said. The company declined to comment specifically on Bahr-de Stefano's case.

'It was acting like a bot'

Bahr-de Stefano noticed the Resy issue on Sunday when he couldn't get into his account. In his email inbox, there was a message from the American Express-owned reservation platform saying that his account had "displayed behavior in violation of Resy's Terms of Service."

He got details about what went wrong after checking Instinct's activity log. Unbeknownst to Bahr-de Stefano, the AI agent had been sending Resy about 200 API requests per hour. That included checking the restaurant's availability through Resy every 10 minutes throughout the day, as well as looking every 0.4 seconds around the time that reservations usually dropped each morning.

That behavior mimics the bots that some people use to snag everything from restaurant reservations to limited-run pairs of sneakers and resell them, Bahr-de Stefano said.

Bahr-de Stefano wrote back to Resy, laying out how he had used the AI agent. The log made clear why his account had been flagged, he said.

"Of course, this account got flagged for spam, because it was acting like a bot," he said.

On Tuesday, an email from Resy informed him that the company had reinstated his account.

It came with a warning, though: If he did it again, American Express could permanently close his Resy account as well as his AmEx credit card. Bahr-de Stefano shared screenshots of the Resy and American Express emails in posts on X.

The tool has worked well in other cases, such as finding an appointment at an otherwise booked-up doctor's office and deciding which attractions to visit in Paris during a trip, Bahr-de Stefano said.

"That was part of what made it really great," he said. "It felt like magic."

The VC said that he plans to continue using Instinct, though with some adjustments. Instead of simply giving the AI agent a simple prompt, he said, he'll now set parameters on how the agent tackles the task, such as how often it pings a website looking for reservations.

"I will probably, in the short term, ask it to lay out a plan and tell me what the plan is before it does it," he said.

At the same time, he added, websites like Resy need to distinguish between legitimate AI agents and those with more nefarious intentions.

"Most of these sellers or providers need to get to a point where they can understand the difference between a verified agent acting on someone's behalf versus a bot farm," he said.

Have a tip? Contact this reporter at abitter@businessinsider.com or via encrypted messaging app Signal at 808-854-4501. Use a personal email address, a nonwork WiFi network, and a nonwork device; here's our guide to sharing information securely.