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Travel

Trips, bookings and getting around · 176 ideas

After a founder left his ID on a plane, the AI autonomously arranged

In a clip from David Senra's interview with Meta's Alexandr Wang (shared on Instagram by someone), Senra recounts a billion-dollar-company founder friend who left his ID on a plane and told the AI he didn't want to be involved in the recovery process at all. The AI arranged a courier, coordinated with building security, went to the office, retrieved the ID, and got it back to him.

Plan my Montreal trip: Airbnb, direct flight and an itinerary that dodges construction

By voice, Simmons asked László for an October 15–18 Montreal trip: a central, inexpensive Airbnb, the cheapest direct flight with an aisle seat, and a plan of things to do. The Dot compared stays, caught repeated complaints about a squeaky Murphy bed at a 4.75-star listing, filled in his flight details from his travel records, rerouted the Mont Royal walk because the cross was under construction, and stopped at checkout for him to pay.

TravelWent wrong

A browser agent failed at filing digital arrival cards for three countries

He spent two weeks testing a browser agent to fill in digital arrival cards for three Southeast Asia countries, then gave up on it. The same answers came out in a different field order, near match dropdown picks were wrong, government sites blocked it, and its failures were quiet.

This one went wrong. See what happened before you try it.

Get my €900 flight refund after the airline said no

After Turkish Airlines refused his delayed-flight refund, a traveler used AI to escalate: it assembled a Turkish-language ombudsman filing with his screenshots and the rule citations, and €900 was refunded. He says he would not have had the cognitive space to do it alone.

€900

Tracked business-class flights from Los Angeles to Rome under $2,000 one-way and

A creator who flies business class but refuses typical prices named her AI 'Miles' and asked it to track business-class fares from Los Angeles to Rome under $2,000 one-way, with flexibility for SFO or SEA. Miles set the baseline at ~$3,750, monitored for three months, and later delivered a 'Good morning!' briefing with five Icelandair fares under $2k from SEA and SFO to Rome.

$2,000

Ping me at 9:20 and tell me to take the bike, not the subway

In the same Vergecast clip, a host describes the AI connected to his Google Calendar: seeing a media dinner party in his evening, the AI advised taking a city bike instead of the subway because it would be faster, and pinged him at 9:20 to leave in time for a 9:30 arrival. The hosts frame it as the AI being proactive to the point of feeling directive.

Find the refund hiding in my inbox

After SAS cancelled and rebooked his family's Oslo flight and a human agent said the dropped prepaid meal fees couldn't be fixed, a father asked the AI to pursue the reimbursement he had never filed since July. The AI searched all his SAS emails and found the airline had already reimbursed the fees the day of the change - buried under that day's notification spam.

TravelPartly worked

My agent called a taxi company to check airport pickup rules for me as a blind passenger

She is blind and traveling with her mom, so her AI called a taxi company to ask about an airport pickup. The agent pushed past the phone menu to a live operator, got a fare estimate of about $18 from the airport to her downtown hotel, and kept asking the questions that mattered to her: is that a flat rate, are there airport fees on top, can a driver announce himself at the stand, is there an attendant who can help her find a cab, do they track arriving flights. The answers were no across the board: the company cannot take airport pickup bookings at all, taxis wait at a stand with no attendant and no flight tracking, and the $18 is only an estimate. She shared the full transcript.

This only partly worked. Worth knowing before you try it.

The AI proactively caught a travel-date mismatch: questioned whether his Singapore-to-Toronto flight was

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.

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Every idea is a real post from someone who tried it, summarized in our words, with a link to the original. App names are swapped for plain words.