Two months across America, planned with AI
Five anchors, every booking, the price drops and an 80-page book.
This summer we took a two-month family trip across the US, built around the World Cup. AI handled most of the planning, and I have to say it was an amazing experience. If I’d had to plan it myself, I wouldn’t even know where to start.
It also went far beyond suggesting a few places to visit. Here’s what it actually did.
It built the route
I didn’t hand it an itinerary to polish. I gave it five fixed points:
- Start in New York (to visit family, and the flights are more convenient).
- Be at 2-3 World Cup matches in the early, not-expensive stages.
- Orlando (parks).
- Miami (for a cruise).
- St. Louis (to visit family).
That’s it. From there it started asking questions, making suggestions and building a route.
The best example is Hershey, Pennsylvania, a place I’d never have thought of going through. Lucky the AI suggested it: a town built entirely around the chocolate factory, with an amusement park and a huge water park, in an area surrounded by Amish communities.
It planned the days
Once we had a route, it suggested a plan for each day and where to stay.
It made the bookings
Every hotel, every flight and every restaurant was handled and booked by AI.
That includes the small questions you’d normally leave for later. It wrote to a restaurant in Brooklyn to ask if we could also reserve the bar upstairs after dinner (no, but there’s a waiting list you join when you arrive), and what “open until 10pm” really meant (10pm is the last reservation, and they stay open until the last party finishes).
It handled the boring parts
This is the part I’d have hated most. AI helped me with the car rental, the insurance, the tolls and fees and everything around them.
It kept hunting for better prices
Booking wasn’t the end of it. AI kept monitoring prices, and when one dropped, it got me a better deal.
Here’s one real example, five nights at a hotel in Brooklyn, with the same room type and the same dates:
| When | Where | Total |
|---|---|---|
| May 14 | First booking | $1,536.79 |
| May 25 | Rebooked after a drop | $1,509.25 |
| June 3 | Moved to another booking site | $1,408.28 |
That’s $128.51 off one stay, without me having to check anything. On June 3 the old booking was cancelled for free and the new one was confirmed a minute apart.
It did the same with flights. Our flight from St. Louis to Las Vegas, for the four of us, went from $735.92 to $499.92 when it rebooked the same flight at the lower price. That’s another $236.
Those two bookings alone saved $364.51.
It helped with the hard parts too
The parks. Orlando was going to cost a lot of money and time, and I had no energy for planning it. So that’s how Park Autopilot started.
The World Cup. AI also helped me get tickets from FIFA, which turned into its own story.
It stayed with us on the road
The help didn’t end when we left. As a rule, every route also came with a story from ChatGPT. In St. Louis, a city I’d never heard of (I couldn’t even have pointed to Missouri on a map), we spent a few days touring and learning the history and culture with the chat.
It created the book
AI created a whole 80-page book covering the entire route: what to do, anecdotes and so on. And we printed it.
If you’re considering something similar, feel free to ask.
This post started as a thread on X.