Planning a trip to the Olympics should feel like preparing for a global celebration. Sometimes, that celebration just requires a bit of creative problem-solving. While wearing ski mittens.
Our base for the Games was north of Venice. It was the perfect sanctuary, but also the starting line for a logistical marathon. This wasn’t just another Olympics; it was officially the most spread-out in history. Events are scattered across the map like someone dropped a box of medals from a great height. It’s an ambitious, beautiful setup, but one that definitely rewards a bit of extra homework.
Unknown knowns
You’d think a global event would have every detail set in stone months in advance. In reality, it was more of a “live” experience. Information arrived in its own time, often with the relaxed pace of a Sunday afternoon. We found ourselves balancing the excitement with a few big questions. Should we drive 6 hours via Milan to the park and ride for Livigno, or take the mountain route and hope for the best at a Swiss border crossing that didn’t take reservations?
The Claude complication
I started with Claude. I wanted specifics. I wanted a plan that didn’t involve me sleeping in a train station. Not a great choice when travelling solo, but with the family? And memories of a truly awful Formule 1 hotel in our memory bank from a few years back? Absolutely not.
What I got was the digital equivalent of a shrug. Claude was superficial. The responses were generic. “Helpful” in that way that doesn’t actually help at all. Worse than the vagueness, though, was the attitude. I’m getting a lot of sass from Claude these days. It’s like talking to a teenager who’s annoyed you asked them to take the bins out. And oh, so judgy.
Enter Gemini
So, I leaned into Gemini. We didn’t just “plan.” We “vibe coded” the entire itinerary. I needed a guide that understood the difference between a “direct train” and a “scenic detour through hell.”
Take the Ice Hockey at Milan Rho Fiera. The transportation links around Milano are legendary, but complex. Gemini helped me realise we could bypass the Milano Centrale madness entirely, finding the direct lines to Rho Fiera and avoiding the “Milano shuffle.”
And what a joy the Frecciarossa trains are. Snacks, water and a buffet car with real food. It was the perfect way to travel. Sidebar: while the venue snacks were… an experience (soggy hamburgers, anyone?), the food in Livigno more than made up for it. Local Italian food always wins in the end. Always.
The Livigno gauntlet
The real highlight was the journey to Livigno.
We weighed up the “Milan side” route versus the mountain approach. We’d been keeping an eye out for the North route park and ride updates, and when the location at Mustäir, no longer Mals/Malles, was confirmed just a week before travel, Gemini’s ability to pull that fresh info together was a lifesaver.
We eventually settled on Silandro (north of Bolzano) as our stopover. A 3-4 hour drive from our base, an actual hotel, and a real sense of progress. Gemini even flagged small details, like the fact that our parking route would take us through a pedestrian zone.
What followed was a beautiful, complex cocktail of replacement rail services and Swiss PostBuses. It was a masterclass in app coordination: SBB for the Swiss legs and Südtirol Mobil for the Italian side, all timed perfectly for the Munt la Schera tunnel.
The “secret stop” and the Olympic spirit
Then came the moment of genuine friction. We navigated the rail replacement bus. Caught the second bus. And then we arrived at the border only to find the “official” Park and Ride location wasn’t where it was supposed to be.
Total panic.
I was looking for a stop that matched my itinerary, but the physical signs were a chaotic blend of Swiss-German, Italian and Romansh. I was looking for “Müstair, Grenze” (the border), but the signs said “Müstair, cunfin.” We ended up overshooting the border stop, hopping off at the very next one in a daze.
And that’s where the “Olympic Spirit” actually showed up. A very helpful American family was already standing there, looking remarkably calm. They assured us that despite what the maps said, we were at the “secret” stop according to their hotel. The exact place we needed to be.
Sure enough, five minutes later, the Line 815 Olimpico Shuttle crested the hill. We were on our way. Within five minutes, we passed the official park and ride, which was covered in snow. The bus had to stop so we could exchange for one with chains to go up the mountain. You could see why Livigno was cut off from the rest of the world in winter until the 1960s.
Intelligence plus human kindness
In a world of automated sass and complicated/broken/lacking in info official sites and portals, the only thing that actually works is genuine, specific intelligence, paired with the kindness of strangers.
We navigated the Olympics with a plan that made sense, managing the transport of five of us across hours of travel by automobile, train, rail replacement bus, and shuttle. The curling in Cortina was intense, the ice hockey was batshit crazy (the Slovakian fans are fun!), and while the snowboarding got canned because the weather was too bad to spot the landings, we had great fun in the snow anyway.
It’s a strange new world when your travel companion is a Large Language Model, but I’ll take Gemini’s precision over Claude’s sass any day. It allowed me to stop being a stressed-out logistics manager and start being a person on a family holiday. We found our way through the snow, the language barriers and the questionable Olympic catering. Proving that while AI can give you the map, you still have to be the one to jump off the bus.
Literally.
Things have a way of working out. You just need a bit of digital logic to get you to the border, and a helpful American family to tell you where to stand once you cross it. Next time, I’ll just remember to pack better snacks and keep a little extra faith in the “secret” stops of the world.
