So companies believe that agents and overall AI will be amazing at booking holidays for us. I see this in every demo possible and, on one hand, I understand why they present it like this, but on the other hand it's the least useful example possible.

Ask anyone you know if they ever told an agent to "Book me my next trip to Lisbon" and let it do everything, including pay for it. I'd bet that almost no one does.

But I'm getting ahead of myself.

Gemini

If you go to Gemini's website right now, you'll get this:

The idea is great in principle. You ask the intelligent AI assistant to do everything for you and it will do it. You might say these things are personal, that no two people will want to fly at the same time. Well, that's the intelligence part of the process. Gemini/Google theoretically knows you and your preferences, and even if it doesn't, you can guide it. Here's how Google pitches it:

Skip the stress of endless filters on traditional book sites by using Gemini as your personal travel app that can find cheap flights and affordable hotels near you. Instead of toggling between a dozen tabs, simply describe your ideal getaway, like a "highly-rated boutique hotel in a walkable neighborhood under $200", and Gemini will quickly pull real-time options from Google Flights and Hotels that match your specific vibe. By acting as a streamlined airfare comparison tool and trip planning assistant, it helps ensure your trip plans stay seamlessly organized and your budget on track.

By the time you finish prompting the agent, it would probably be better to go to a specialized website and do it yourself. Also, people rarely travel alone, and if you're like me and try to book a trip for the family, you always end up looking at the same screen together, looking at destinations, reviews, etc. in Booking.

Speaking of Booking.

Booking.com

Back in 2023, they launched Booking AI Trip Planner "powered in part by OpenAI's ChatGPT API", where you could chat with it to book holidays, but unless I disabled something, I just opened my Booking page and there was nothing to be seen three years later. You would think that one of the biggest booking sites in the world would be a text prompt by now if this was indeed the future, but it isn't. They understand that people like to pick, check reviews, check the photos and understand if it would be a good fit for them.

So what's the issue?

The obvious failure

In my opinion, there's always a battle going on in your head about cost vs benefit, and that's something that is hard to replicate with AI. You always want the best possible deal for what you're going to get in return, unless you're so rich that money is meaningless, but if this is the case, you would not be using these sites anyway.

When you look at a hotel or a flight, you see the price and you do the mental calculation. I'm not saying it's accurate, but it's what you "feel" is the best for you, and this greatly influences your decision. This is not something that you can ask AI for. AI can propose flights to you at 3pm, but you could think about going at 6am to take advantage of the day. For other people, a 3pm flight would be better because then you can do other stuff in the morning or arrive at the airport with time to spare.

It's highly subjective, so why is it the go-to example?

It's relatable

They do it because it's relatable. Or rather, it would be wonderful if it existed. People travel and would love not to go through the process of booking holidays. Asking an AI agent to book my perfect holiday to take full advantage of a place without me doing hours upon hours of work would be great. Plan an itinerary, book the flights, do everything for me so that I can just pack and go. Who wouldn't like that?

But, as I'm writing this, it's basically impossible to get it right, or even close to right. This doesn't mean that there aren't companies trying to do it, and the one that really cracks this code will be the one that will make a lot of money, but they depend a lot on the main providers like Anthropic, OpenAI or Google, and these companies are free to launch their own services as we've seen above with Gemini.

Apple tried to come up with better and simpler examples a couple of years ago when they introduced Apple Intelligence, and even they, with all their money, couldn't ship that correctly. Simple questions like "When is my mom's flight landing?", for example, were promised but not shipped. That's a whole other story.

Final Thoughts

Automation can get you very far, and this site is dedicated to showing you how. In this case, though, there's still a long way to go before you can stop doing it yourself.

But if you find a great site that does this properly, please let me know, and I would be more than happy to use it if it saves me time and amend the article :)

Sources

• Booking.com launches new AI Trip Planner (Booking.com press release, June 2023)
• Apple delays Siri AI improvements to 2026 (CNBC, March 2025)
• Apple is delaying the 'More Personalized Siri' Apple Intelligence features (Daring Fireball, March 2025)
• Apple delays some anticipated Apple Intelligence features (Six Colors, March 2025)

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