Coach Casey Kenny asked his AI 'Milo' to book a flight for an October 21 keynote in Dallas; Milo returned United options and Kenny selected option 3. The video shows the actual booking interaction for a business trip.
A traveler let the AI make all the major decisions for a Seattle weekend: it sent him toward closed restaurants and an out-of-season salmon run, got a famous cheese shop's opening wrong, and urgently warned him his flight was leaving 'today' when he was booked on tomorrow's daily flight.
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When a restaurant booking of the writer's was canceled, his dot found him alternative tables on its own initiative, part of a few days of proactive schedule and logistics management after he connected it to his Google account.
With five days' notice, her AI Romy reviewed 51 saved 'Costa rica' reels, built a 5-day itinerary (Bajos del Toro, La Fortuna, Monteverde), found and held Miami-San Jose flights without purchasing, and searched for a dry bag pending her approval; the reel ends with footage from the trip itself.
Stuck in Manhattan with three hours after a drop-off, Eric planned aloud with Jarvis while driving: they weighed a museum, galleries and an observation deck against the mood he wanted, and Jarvis produced a Chelsea gallery walking route. At the end of the call he told it to put the plan in his calendar, and it did.
Ahead of a Nov 14 Disney cruise, he credits the AI with tracking the staggered booking milestones — excursions opening in August, online check-in, and a late-night Royal Gathering character meetup — so none of the windows are missed.
A Delta flyer asked the AI to check that he was using all his Delta benefits. The AI could not get past the robot check screen on delta.com, even when he took over the browser and clicked it himself. Every login try was blocked.
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A first-person account of testing the AI to fully plan and book a spontaneous trip without doing research: an open-ended goal (good food, beautiful stay, minimal effort). The AI compared destinations, flights, and hotels, noticed the author's saved Instagram folder for Mexico City, suggested ways to use points and travel benefits, and organized everything into a bookable plan — presented as Part 1 of a series.
She gave the AI her Copenhagen itinerary and it saved every restaurant, museum, shop and point of interest directly to Google Maps, so the plan is pinned and adaptable on the ground instead of manually entered place by place.
In a skit-style demo, her AI Aaron P offered three date options (a wine bar, a BeltLine stroll plus Ponce City Market, a brewery with games); she picked the BeltLine plan and it was locked to her calendar for Sat Sep 26, 4:00-7:00 PM with parking tips and a reminder offered.