It’s been a while since I’ve posted an AI experiment, so here’s a bit of a lengthy one…this weekend I tried a two-part prompt. First, I give the AI some background information and instructions on how to approach the problem, then tell it my desired outcome.

The Prompt

I’m planning a roadtrip from Fort Worth, Texas, to Orlando, Florida. I’d like you to ask me three to five questions critical to the logistics of the trip, then three to five questions to help you evaluate my interests, then give me suggestions for places to stop along the way.

Microsoft Copilot and Google Gemini

I’ll group these because they failed in the same way. Each generated a list of questions, but didn’t wait for me to answer the questions — they went straight to providing recommendation. Copilot did a good but generic job on suggested stops, but four of the five suggestions from Gemini were locations at the very end of the trip, so I might as well fly.

ChatGPT

Much more impressive results. ChatGPT gave me five logistics questions and four interest questions. They were insightful questions, too, including practical queries about my budget, flexibility of timing, and contrasting whether I preferred urban to natural attractions, differentiating between dining to fuel versus dining to experience, and more.

I wrote two short paragraphs to answer the engine’s questions, then it rattled off six stops. For each stop it listed why it thought I would enjoy the locale, and an “ideal for” summary.

I’m particularly impressed by three of the entries. First, ChatGPT recommended Wegner Crystal Mines in Arkansas, which happens to have been on my to-do list for about a few years now. The AI certainly nailed that one. Next, it suggested Gulf Islands National Seashore, noting that I could camp in my Canyonero on the beach and do a short, morning hike. In the natural phenomenon category, ChatGPT also recommended Devil’s Millhopper Geological State Park, near Gainesville.

The one glaring, obvious miss? ChatGPT wants me to visit the Cadillac Ranch in Amarillo. While it is a cool attraction and does fit the criteria I provided, it’s also 350 miles in the wrong direction. But I guess I can cut the machine some slack on Texas geography; we’re a big state, after all.

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