The worst part of travel is the planning: the faff of finding and booking transport, accommodation, restaurant reservations—the list can feel endless. To help, the latest wave of AI agents, such as OpenAI’s Operator and Anthropic’s Computer Use claim they can take these dreary, cumbersome tasks from befuddled travelers and do it all for you. But exactly how good are they are digging out the good stuff?
What better way to find out than deciding on a last-minute weekend away. I tasked Operator, which is available to ChatGPT Pro subscribers, with booking me something budget-friendly, with good food and art, and told it that I’d prefer to travel by train. What's fascinating is that you can actually watch its process in real time—the tool opens a browser window and starts, much as I would, searching for destinations accessible by rail. It scrolls a couple of articles, then offers two suggestions: Paris or Bruges. “I recently went to Paris,” I type in the chat. “Let’s do Bruges!”
Armed with my decision, Operator goes on to look up train times on the Eurostar website and finds a return ticket that will take me to Brussels and includes onward travel within Belgium. I intervene, however, when I see the timings: It selected an early-morning train out on Saturday, and an equally early train back on Sunday—not exactly making the most of the weekend, I point out. It finds a later return option.
So far impressed, I wait to double-check my calendar before committing. When I return, however, the session has timed out. Unlike ChatGPT, Operator closes conversations between tasks, and I have to start again from scratch. I feel irrationally slighted, as if my trusty travel assistant has palmed me off to a colleague. Alas, the fares have already changed, and I find myself haggling with the AI: can’t it find something cheaper? Tickets eventually selected, I take over to enter my personal and payment details. (I may be trusting AI to blindly send me across country borders, but I’m not giving it my passport information.)