Planning a week-long trip used to mean forty open tabs, a spreadsheet, and a sinking feeling that I'd still booked the wrong hotel. This time I handed the whole job to AI: ChatGPT did the brainstorming, Wanderlog turned it into a real route on a map, and Gemini double-checked everything against my actual bookings. Here's what actually happened — the wins, the facepalms, and whether I'd do it again.
The Brain: ChatGPT Did the Thinking
I gave ChatGPT a budget, seven days, and a vague vibe ("beaches but not boring beaches"), and it came back with a day-by-day plan that was honestly better than my own first draft. It grouped attractions so I wasn't zigzagging across the city, remembered my dietary restrictions from the first message, and even flagged that driving a certain coastal road in summer would be miserable — trains instead. The free tier handled all of this fine; Plus costs $20 a month if you want the fastest models. The catch: ChatGPT is a researcher, not a booking agent. It confidently suggested a hotel that had been sold out for months, and one flight connection only existed in its imagination. Rule number one of AI trip planning: never book straight off the AI's word.
The Map: Wanderlog Kept Me Honest
A list of days is not a trip — a trip is a map. That's where Wanderlog earned its keep. Its drag-and-drop itinerary shows every stop clustered geographically, so I could see immediately that Day 3 had me crossing the same bridge four times. The free tier covers unlimited places, live collaboration, and the map view, which was enough for my whole trip. Wanderlog Pro costs $39.99 a year and adds offline maps, route optimization, and booking-deal alerts — worth it if you travel where data doesn't reach. One nitpick: the AI suggestions on the free plan are capped at about five messages per trip, so do your chatting in ChatGPT and your mapping here.
The Fact-Checker: Gemini Knew My Inbox
Gemini (free with a Google account) did something the others couldn't: it read my Gmail confirmations and pulled my actual flight and hotel bookings into the plan. It also pulled live pricing from Google Flights and Hotels, and caught a "great deal" ChatGPT had quoted that had quietly risen by $60. If you live inside Google's ecosystem, this is your pre-trip audit. Let Gemini verify the plan before you pay for anything.
What I'd Do Differently
First, verify every price, flight time, and hotel before booking — AI still hallucinates connections and sold-out rooms. Second, book through real airline and hotel sites, not the AI's links. Third, keep one buffer day empty; the best parts of the trip were the ones no AI scheduled. Total cost of my AI planning stack: zero dollars. The verdict? AI didn't replace the travel agent — it replaced the forty tabs. The boring legwork that used to eat a weekend now takes an evening. I'm letting AI plan my next vacation too. I'm just not letting it touch my credit card.
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