Travel creator Jorden Tually, who says trip planning is exhausting after 4,000+ days of continuous travel, demonstrated the AI on Instagram on Oct 16, 2026. He asked for a spontaneous weekend away under $500; the AI built a Washington, D.C.
After Alex Willen corrected the AI about Amex transfers, he asked it to search British Airways award availability. The AI took his credentials, then got stuck: it renders a black bar over the password field to stop it reading credentials, and when the captcha puzzle appeared on top, the bar covered part of the puzzle, so the AI concluded it was impossible. Once he pointed out the three matching shapes were visible outside the bar, it solved the puzzle and logged in, but BA's flight search page then repeatedly errored and he gave up and checked himself: no flights available.
This one went wrong. See what happened before you try it.
His scheduled search looks 8 days to 12 weeks out for same day return flights from Stansted under £30, and checks Eurostar promo fares too. The point is the tobacco run: 200 cigarettes cost him about £150 at home and about £50 abroad, and he gets a day in a city he would not normally visit out of it.
A screen recording shows a proactive AI message: TAP Portugal selling Montreal (YUL) to Lisbon roundtrip nonstop for $602 CAD all-in — 34% below typical best prices — noting it pairs with Manchester United's Champions League away game at Sporting CP on Wednesday, Nov 25 at Estádio José Alvalade. A user reply reads 'the AI is my new travel agent.'
Leo Batistella (Portuguese-language creator) showed a chat where his AI listed his itinerary — Oct 9 Bali to Shanghai, Oct 10 Shanghai to Singapore (early morning), Oct 11 connecting in Singapore to Toronto without leaving the airport — then questioned whether the Singapore-Toronto leg was Oct 11 or Nov 11, noting his Toronto hotel is booked Nov 11-15. Without being asked, the agent checked his ticket and confirmed the flight is in October, not November.
A commenter says he feeds the AI his booking details and complaint and lets it negotiate petty corporate disputes. For a Milan hotel stay, the AI first won a free night he rejected, then a 25% reimbursement he accepted.
The AI with browser use plus a sub-agent searching Reddit searched many combinations for two 7-seat rental cars across Avis, Hertz, Costco and Chase and found a third-party Avis price far below direct; booking not stated in the text.
This only partly worked. Worth knowing before you try it.
A traveller's the AI checked him in for his flight automatically as soon as check-in opened. It told him his boarding group and sent him his boarding pass, with nothing for him to remember or open.
His wife works for an airline, so he flies standby through an employee perks app that normal flight apps do not cover. He has the AI track every change. This weekend the AI caught his original flight at Y0, meaning no spare seat, so he switched flights and still made it to Vancouver. The AI checks more often as departure gets closer and only tells him when something changes, and it sends his wife short Messenger updates on his chances of getting on. His tally for the weekend: 2 flights boarded, 1 full flight avoided, 1 gate change caught, no app refreshing from him.
The AppleVis reviewer told the AI he knew he had unused Southwest credits and wanted to use them to book a flight to Nashville. The AI located the credits and autonomously booked the flight.