I’ve been experimenting with AI/large language models for work, mostly to see how well they handle language-based tasks. They’ve proven to be excellent at things like translation and cleaning up speech—way better than I expected. But I never imagined they could assist with something like route planning and provisioning for a trip.
I’m planning a trekking trip to Greenland this summer, exploring a couple of different areas. While communicating with local outfitters and guides, I realized that working in English was creating some challenges. I thought it’d be smart to translate all my communication to make things clearer on both sides.
So, I wrote up my detailed itinerary and headed over to Anthropics’ Claude model. In my excitement, I forgot to give it the explicit command to “translate this” and instead just pasted my entire letter to the outfitter/guide. The AI ended up processing my whole itinerary instead.
The results were both impressive and a little unsettling. Here’s what I got back:
https://claude.site/artifacts/1ca52510-de1b-443f-b96c-18a3f4c1c3fb
I’m now systematically going through the response out of curiosity, and so far, it seems surprisingly accurate. That said, it rounded the GPS coordinates to just one decimal place, which has moved some waypoints and campsites into the middle of bodies of water. Not ideal.
When I followed up to ask it to refine the GPS coordinates, things took a strange turn—it started hallucinating and generated a three-week itinerary for the John Muir Trail! No matter how I prompted it, I couldn’t get it back on track to refine the original itinerary.
I figured this might be interesting for this group—both as an example of the strengths of these tools and as a cautionary tale about the occasional weirdness they produce.
For those that are an interested, here is my original reqest that ended up being the prompt for the LLM:
I will be in Greenland during the second half of August 2025, arriving in Narsarsuaq from Nuuk on <Date time>.
My wife and I are avid solo hikers, so while we don’t require a guide on the trail, we would appreciate support with the logistics and planning. If your company offers services to assist with these aspects, we’d love to discuss hiring them..
Our initial plan is a five-day hike from Itilleq to Qaqortoq, with one night in Qaqortoq, where we’d like lodging that includes a bath and electricity (nothing fancy). We’re told the view from the top of Mt. Killavaat is spectacular, so we’re considering adding that to our route.
I would like to rent or buy bear spray, flares, and buy gas. Afterward, we’re interested in a resupply at Qaqortoq, followed by a journey to Tasermiut Fjord. From there, we’d like to hike to the col above Tasiusaq. We are still finalizing the details of this section, but Tasermiut is a priority for us. Here’s a summary of the assistance we’d need:
1. Boat transfer from Narsarsuaq to Itilleq on arrival.
2. Transporting a single bag from Itilleq to Qaqortoq for collection upon our arrival there.
3. Arranging transport to and from our hike in Tasermiut Fjord.
4. Return transportation to Narsarsuaq by <date Time>
If there are any alternative routes or scenic spots around Tasermiut that you’d recommend, please feel free to share.
We’re open to adjusting the itinerary for memorable experiences. Some have suggested changing igaliku in favor of Tasiusaq. I welcome your suggestions.

