AI Planned My Vacation-Here’s What Happened

▼ Summary
– AI travel agents like OpenAI’s Operator and Anthropic’s Computer Use aim to simplify trip planning by handling tasks like booking transport and accommodations.
– The author tested Operator by requesting a budget-friendly weekend trip with good food and art, preferring train travel.
– Operator suggested Bruges after the author ruled out Paris, then searched for Eurostar tickets and adjusted timings based on feedback.
– A session timeout forced the author to restart the booking process, revealing a limitation where Operator doesn’t save progress between tasks.
– While impressed, the author manually entered payment details, showing reluctance to share sensitive information with the AI.
Planning a vacation can be exhausting, scouring websites for flights, comparing hotel prices, and mapping out itineraries often feels like a second job. To test whether artificial intelligence could handle the heavy lifting, I put one of the newest AI travel assistants through its paces. The goal? Organize a last-minute weekend getaway with specific parameters: affordable, culturally rich, and accessible by train.
Using Operator, an AI tool available to ChatGPT Pro users, I outlined my preferences, good food, art galleries, and rail travel. Watching the system work was intriguing. It opened a browser window, mimicking human behavior by scanning travel articles before suggesting two destinations: Paris or Bruges. Having recently visited Paris, I opted for Bruges. The AI then pulled up Eurostar schedules, locating a round-trip ticket to Brussels with connections to Bruges.
There was a hiccup, though. The initial itinerary included an early Saturday departure and an equally punishing Sunday return, hardly ideal for maximizing weekend relaxation. After pointing this out, the tool adjusted the schedule, offering a more reasonable afternoon train back. Just as I prepared to finalize the booking, the session expired. Unlike standard ChatGPT, Operator doesn’t retain conversations between tasks, forcing me to restart the process. By then, ticket prices had shifted, leading to a back-and-forth negotiation with the AI to find a better deal.
Once the logistics were settled, I took control to input payment details manually. While comfortable letting AI book transportation, I drew the line at sharing sensitive passport information. The experience highlighted both the potential and limitations of AI travel planning, impressive efficiency paired with occasional frustrations. For now, human oversight remains essential, but the technology is undeniably inching closer to becoming a reliable travel companion.
(Source: Wired)