How are you using AI for trip planning? | Question of the Week Ep7 | 6-27-26

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How are you using AI for trip planning? Frequent Miler reader Jared wrote in:

I recently asked the Bilt Neighborhood Concierge AI which weekends a particular Bilt Home Away from Home hotel (Kimpton Journeyman) had availability between August and December. It gave a useful and seemingly accurate response. Have you recently found any other good uses of Bilt’s or other AIs?

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Caroline Yoder
Carrie Yoder spent more than 5 years as a digital nomad, traveling to 70 countries and working behind the scenes with Drew Macomber to help build and manage the popular points and miles travel blog, "Travel Is Free". Now she uses the content management, digital media, and design skills she learned then with Frequent Miler.
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3 Comments
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N.W.

Using Gemini.Ai on my last trip to China screwed me over so many times with inconsistencies and wrong information. When I asked it to double check, it would change it answer. When I’d ask it if it was Positive, it’d change back to the first answer (which ended up wrong). Ended up costing me a non-refundable $800 wasted on a last minute flight. Gemini.ai Cost me an extra $300 on luggage it said was free. Mind you I have incredibly detailed information to get the most accurate response.

Tom

Excellent

Jo Ann

Great podcast and question! I have been using AI for my trip planning. I want to see x, y, and z. I want lazy afternoons for a short nap or a coffee break. Build me an itinerary so I ma not backtracking all over the city.

I also use it to help me pack. I am taking this number of tops, pants and dresses. Build me a day to day wardrobe based on the itinerary. I look at the list each morning and get dressed. I do adjust based on weather, etc.

It has been very helpful to me but will never replace the human component of the points and miles game!