Booking.com’s new AI trip planner: I tried it and all I got was this lousy itinerary

How many times can one travel planner AI send you to the Sky Tower? Very many. Photo / Michael Craig

Greg Bruce is a senior multimedia journalist for the New Zealand Herald who has reported extensively from the front lines of the generative AI revolution.

OPINION

A few weeks ago, I received an email about the launch of Booking.com’s AI Trip Planner, which was described as “a new conversational experience to help improve the holiday planning experience for Kiwi travellers”.

As someone who has been an early and enthusiastic adopter of AI, and believes it is basically magic, I had high hopes for this app. So it was with some sadness and disappointment that I read its response to my request for a three-day itinerary for my home city.

It read less like the product of one of humanity’s greatest technological achievements and more like the half-assed thoughts of an American tourist who came here once, 20 years ago, and spent most of their time in their hotel room, reading the free magazine they got at the airport.

It suggested I visit the following, in order: Sky Tower, art gallery, domain, museum, Waiheke, viaduct, harbour bridge and Devonport.

I have nothing against any of these places, which are of course all nice in their own ways, but I was hoping to be inspired and excited by the AI’s output, not dropped directly into the soulless maw of Big Tourism.

I have used generative AI often enough to know it sometimes needs to be pushed to produce its best work, so I followed up by requesting a 21-day itinerary, figuring that would ensure I received at least a few hidden gems.

Instead, I got exactly the same insipid three-day itinerary, followed by 15 days in Rotorua, Coromandel, Tongariro and other places that weren’t Auckland. For days 19-21, it wrote: “Spend your last few days in Auckland, exploring any attractions you may have missed earlier or simply relaxing and enjoying the city.”

“Attractions you may have missed”? “Relaxing and enjoying the city”? I couldn’t believe a technology that famously has an answer for everything would meet its match with the question “What is there to do in Auckland?”

I asked it to show me the city’s hidden treasures. I wrote: “I want to explore and live life!”

This time, it at least limited its recommendations to Auckland, but they were still extraordinarily limp: The Sky Tower, art gallery and museum, followed by three-day stints in Ponsonby, Devonport, Parnell, Mission Bay and Newmarket.

I replied: “Look, I’ve been to Auckland heaps and know all this stuff and it also appears in all the tourist guides. I have come to you to be inspired and to find new, exciting, hidden treasures.”

To its credit, it suggested some out-of-the-way places: The Wintergardens, Silo Park, Western Springs Park, Mount Albert/Owairaka, Onehunga. These were pretty good suggestions for a drunken teen on a night out with friends but, still, I liked that the AI was trying.

I wrote: “This is a bit better but quite vague. While keeping in mind my imploration for you to be edgy and think outside the box, can you be more specific? Rather than just area names and landmarks, can you give me specific places and organisations and shops and attractions and people?”

It offered a few more brief flashes of inspiration: some night markets, Kelmarna Gardens, Auckland Theatre Company, the fish market. But when I encouraged it to keep going, it lost its mojo and returned to the well-trodden ground of the museum, harbour bridge, zoo, botanic gardens and – inevitably – the Sky Tower.

Again, I asked it to try to be inspiring. Again it appeared to try. It suggested Spookers, a ghost tour, a street art tour. Because I suspected some of the places and activities it came up with were either lame or defunct, I asked for contacts, but it told me that it didn’t have access to such information.

Still, I felt we had made some progress and that I had shared enough about my needs and desires for the AI to produce a genuinely decent 21-day Auckland itinerary, so I asked it to do so.

It started promisingly enough. The first three days included the night markets and Kelmarna Gardens and were followed by a pleasant-sounding spell on Waiheke, but then it all fell apart. Days 7-9 were in Coromandel, days 10-12 the Bay of Islands, days 13-15 in Rotorua, and 16-18 in Taupō. Most astonishing of all, it suggested I spend the final three days in the Waitomo Caves. Not just in the area, but actually in the caves. That sounded not just extremely boring but downright scary.

“I hope this itinerary meets your expectations and helps you plan your ideal 21-day trip to Auckland,” it wrote, apparently unironically. “Let me know if you have any other questions or if you need help finding a place to stay in any of these locations.”

I didn’t have any other questions, and if I did I would not have directed them to the AI. We hadn’t needed to spend much time interacting for it to become clear I could put in much less effort and get much better answers by talking to either a travel agent or any randomly selected foreign tourist lost on Queen St – English a bonus but not at all necessary.