Prologue

Christopher has been busy with all the things around the Esri UC, so this is Holly, here to share some recent AI shenanigans of my own.

I have written before about my evolution around using AI, from occasional email-drafter to full-on thinking partner. Recently, though, I had a new experience: a fully AI-planned road trip.

There are a few things that led to this:

1. My husband and I have been watching the show Fargo (we’re on Season 3, no spoilers!)
2. We were trying to figure out some summer plans, and making sure we use all our vacation time for the rest of the year.

Somehow, this led to the idea that we should go explore Fargo over the 4th of July weekend, which would be the first visit to North Dakota for both of us. (And yes, I get the irony that much of the movie and show both actually take place in Minnesota.)

But what to do with a weekend in Fargo? I did a few half-hearted internet searches, but Jeff decided to put it to his preferred AI friend, Gemini. He gave it some context about what kinds of things we usually like to do on vacation—interesting historical sites, hiking in scenic places, and areas with cute shops & good restaurants—and it created a whole itinerary.

At first, I thought that itinerary would be a starting point. We’d pick it apart and add in other ideas. Often, when planning a trip, I find myself pulling from random Reddit threads, travel blogs that come up in my searches, recommendations from friends, and sometimes even old-school printed travel guides. I have a whole process for this!

This time, though, we were busy with other things, and suddenly the trip was upon us. Neither of us had come up with anything besides what Gemini pulled together for us, and so… we just kind of went with it. Gemini, take the wheel! (Not literally, we still had to do the driving.)

Here’s how it went.

Fargologue

Wednesday Night (Des Moines to Sioux Falls, SD)

What Gemini said:

• The Drive: Leave home in the afternoon/evening for the ~4-hour drive northwest to Sioux Falls via I-80 W and I-29 N.
• Lodging: Check into a downtown spot like Hotel Phillips (a restored 1918 bank building).
• Evening: Enjoy a relaxing dinner or craft cocktail at The Treasury inside the hotel before getting a good night's rest.

What we did:

Well, we drove, of course. We were not as classy as Gemini with our dining, stopping instead at a Perkins in Sioux City, Iowa, because it was right off the interstate and also because pie. That was underwhelming, and we vowed we would listen to Gemini more. However, we also checked into whatever hotel we could find with the cheapest rate online for the night. So, nothing about this leg was really enhanced with Gemini.

Thursday (Sioux Falls to Fargo)

What Gemini said (slightly abbreviated here):

• Good Earth State Park (Just Southeast of Sioux Falls)
  • Start your morning right outside the city at one of the oldest locations of human settlement in the country. This peaceful site was an ancient, massive trading hub for the Oneota peoples from 1500 to 1700.
• Nicollet Tower & Interpretive Center (Sisseton, SD)
  • Stop to climb this 75-foot stone and timber observation tower, built to honor Joseph N. Nicollet, the French cartographer and astronomer who map-made the region in the late 1830s. The top offers a panoramic view across the ancient glacial valleys of three states.
• Fort Sisseton Historic State Park (Lake City, SD)
  • The Highlight: Take the scenic 30-minute drive west of the highway into the Coteau des Prairies hills to explore this beautifully preserved Civil War-era frontier outpost. Established in 1864 under the direction of Major General John Pope, it was built to protect settlers and surveyors moving through the territory.
• Evening Arrival in Fargo: Drive the final 1.5 hours north to Fargo. Check into the Hotel Donaldson, unpack among the original 19th-century timber beams and local art, and head to Mezzaluna for an upscale dinner.

What we did:

The first thing we did was go see The Falls of Sioux Falls! They are right downtown, located in a really nice park, and very cool. So, that was a bit of a miss by Gemini.

After that, we followed Gemini’s agenda. At Good Earth State Park we did a short hike and visited the museum where we learned this park is part of the larger Blood Run National Historic Landmark, which crosses over into Iowa.

We stopped, as instructed, at Fort Sisseton and Nicollet Tower on our way to Fargo. I gotta say, Gemini really oversold the cartography angle about Nicollet Tower. I was expecting to at least see some interesting signage about historic maps—maybe you had to go inside the Visitors Center for that. Regardless, we climbed to the top and checked out the views.

Upon arrival in Fargo, we checked into our Airbnb and got tacos for dinner, veering off Gemini’s agenda. Mezzaluna did in fact look amazing, but we never made it there!

Friday (Around Fargo)

What Gemini said (abbreviated):

• Fort Abercrombie State Historic Site
  • Head 30 minutes south of Fargo to complete your frontier fortification study. Established in 1858, this was the first permanent military post in the North Dakota Territory and was besieged for over six weeks during the U.S.-Dakota War of 1862.
• Lunch: BernBaum's
  • Return to downtown Fargo for a unique, mid-century modern culinary experience that blends Jewish deli staples with Nordic flavors (like house-cured lox and artisanal knishes).
• Afternoon Prairie Walk: Buffalo River State Park (Minnesota side)
  • Spend a peaceful afternoon 20 minutes east of Fargo exploring a massive block of virgin tallgrass prairie.

What we did:

At this point, we were pretty trusting of Gemini’s agenda, and we went with it without asking too many questions.

I mean, of course, we needed to complete our frontier fortification study. At Fort Abercrombie, we were pleasantly surprised to hear that our $10 entry got us into the museum AND a personal golf cart tour with their site interpreter, a college student who told us she got the job a few years ago at 16 because literally all the other jobs available to teenagers were a 30-minute drive from home. The state had then raised the minimum age to 18, so she lucked out. Anyway, I don’t know that we would have ventured to this site without Gemini, and it was definitely a good stop. There’s not a lot around here in 2026, yet in the 1860s it was part of the “gateway to the West” and also played a role during the U.S.-Dakota War in 1862. There’s a lot of interesting—and sad—history in this spot that you could easily miss.

I left in Gemini’s lunch suggestion above as a reminder that you can’t always rely on the AI (yet?). Does that restaurant sound amazing? Yes. Did it permanently close in 2024? Also yes.

Thankfully, we checked on that first, and found a different lunch spot on our way to Buffalo River State Park for an afternoon hike. I feel like a major learning from this trip was to not sleep on state parks!

Dinner was at Brewhalla, a food hall/beer hall/hotel in Fargo that Gemini missed.

Saturday (Happy Birthday, America)

What Gemini said (abbreviated):

• Bonanzaville’s 4th of July Celebration (West Fargo)
  • Explore this sprawling pioneer village of 43 historic buildings.
• The Hjemkomst Center (Moorhead)
  • Examine the incredible human story behind the Hjemkomst, a full-scale Viking ship replica that a local crew sailed across the Atlantic to Norway in 1982. Step outside on the grounds to tour the Hopperstad Stave Church, an intricate, hand-carved replica of a 12th-century Norwegian house of worship.
• Optional Evening Tradition: The Combine Derby
  • If you're up for an unforgettable slice of local culture, head to the opening weekend of the Red River Valley Fair for their grandstand Combine Demolition Derby. If you'd prefer a quieter evening, opt for fine dining at Rosewild followed by an evening stroll down Broadway.

What we did:

We started the day at a cute coffee shop downtown, which I had to find with my human skills, because our Gemini itinerary did not account for morning coffee. (Note to self: next time, prompt the AI to give me a fun coffee shop for every day; sorry Jeff.)

We flipped the order and embarked upon the 4-minute drive to the Hjemkomst Center in Moorhead, Minnesota. Nothing about the description of this museum sounded very exciting to me, but…

I was delighted to be proven wrong. The Hjemkomst Center is essentially a monument to two guys with dreams. The first, to build a replica Viking ship and sail it to Norway, and the second, to build a full-scale replica of a 12th-century Norwegian church. So yes, a replica ship and a replica church, but the stories about these coming together were pretty great.

From there, we followed Gemini’s other lead, to Bonanzaville, a museum/village of early settlement life in North Dakota. Free admission on July 4 (score!), so we just walked around, checking things out, until we were too hot and tired.

Did we go to the Red River Valley Fair for the Combine Demolition Derby? I’ll leave that one a mystery.

Sunday (Home)

What we did:

Not much to report here from Gemini or us; we took a different route home, around Minneapolis, but no exciting stops.

Maps!

Oh, right, this is a GIS audience, so I did take pictures of a couple of maps to share!

Conclusion

Would I let AI plan another vacation for me? Heck yes! Though I still do enjoy the process of researching, building a plan, and finding some hidden gems. So, I probably won’t fully hand the whole thing over to AI, the way we did this time.

I did remember that I have years of plans from previous trips saved, so I could also give them to AI for more context on the next plan!

I'm excited to see how much we'll be able to rely on AI agents to search for hotel and flight deals in the future. That’s one area that still feels pretty manual when you have a lot of variables.

Newsologue

Jaws has been writing this section, but I’m not sure what else Christopher has Jaws working on from the UC, so this is human-sourced too!

• New York becomes first U.S. state to impose AI data center ban. This is a one-year, state-wide moratorium. I also saw a one-year ban from the City of Pensacola, so it seems like this conversation is just getting started. Surveys show that in NY, the idea was popular, with bipartisan support.
• Chinese startup Moonshot AI unveils Kimi model it says rivals OpenAI, Anthropic. The report says that the new model surpasses Claude Opus 4.8 and GPT 5.5 on some benchmarks, but trails behind Claude Fable 5 and GPT 5.6 Sol on overall performance. This, of course, is according to the company, so take that for what it’s worth. Relatedly though, Morning Edition reported this week on US startups turning to Chinese AI models due to cost. Like the data centers, this is another topic that’s not going anywhere.
• Netflix revealed this week that they used generative AI on about 300 programs so far this year. Their spokespeople are saying this is a tool, not meant to replace human creatives. I am sure there’s a lot of skepticism around this, but I am also a proponent of using AI for things it can do well, while maintaining human energy/creativity/ingenuity for where that matters most—and there must be room for both in the entertainment industry. Right?

Epilogue

I, Holly, wrote this out, and then I gave it to Claude to help refine. Like Christopher, I want to keep my writing in my voice, so I usually tell Claude not to rewrite it. In the interest of transparency, I will go full Christopher and share my prompt:

I have drafted a guest post for Christopher's newsletter about my recent trip to ND. I want you to help me with line edits, not a full rewrite. The tone should be a little fun and quirky, as is. Just tell me places it could be smoother, clearer, funnier. Gemini's sections are quoted so we can't change them.

I did revise quite a few sentences with Claude’s help, but I think it still sounds like me!

Christopher [just a little] edited from there.