Adventures in Trip Planning

Testing AI for my 2026 Wyoming Cutt-Slam

I love trip planning. Researching details, timing routes, meals, accommodation, and all the hundreds of other details involved in a successful outing — that's half the fun. And with the increasing power of online resources, software tools, and yes, even AI, planning is easier and more precise than ever. My upcoming Wyoming Cutthroat Slam attempt is a perfect example.

I've always been a fan of maps and guidebooks, and chatting with friends and officials for beta. I got more proficient after taking Andrew Skurka's Plan Like a Pro course before my 2012 Escalante Adventure — that, combined with going down the ultralight backpacking rabbit hole, set the foundation for my process today.

The Wyoming Cutthroat Slam was developed by the Wyoming Department of Fish and Game to promote awareness of the state's four native cutthroat subspecies: Bonneville, Yellowstone, Colorado, and Snake River Fine Spot. More awareness means more support for conservation. The fish are found in four distinct watersheds, predominantly in remote southwest Wyoming.

There's no required timeframe for completing the slam, but I thought it would be fun to attempt it in a single season over two weeks. Fishing all the watersheds surrounding the Wind Rivers from my home in Washington takes serious planning — stream flows, access, hatches, flies, public land, and more.

I started plotting rivers and routes in CalTopo, then paused: Can AI play a supporting role here? Turns out the answer is yes — in spades. I developed this prompt:

"Starting {date} I will take a 14-day fishing trip traveling from my home in Vancouver to SW Wyoming, where I will fish {the target rivers}. I want to spend two full days fishing each river. I want to drive only during daylight hours, from 6 AM to 8 PM. I will drive mainly on improved highways but will travel on gravel roads adjacent to the rivers I fish. I will camp (boondock) on BLM and state land. Create a travel itinerary that minimizes driving time and miles as much as possible, and optimizes for maximum fishing time."

I fed it to Claude, ChatGPT, and Gemini, then fact-checked the outputs with Google Maps and CalTopo. My verdict: these dogs are ready to hunt. Follow-up prompts generated a matrix of the top five flies for each river, and I'm now at the vise stocking the box for my 2026 Cuttslam.

Will AI replace my trip planning process? No — leaning on it too heavily would be risky, much like how Instagram has become a hazard for the inexperienced. But it's a great tool, and it'll definitely have a place in my future adventures.