The Drive From Milan to Cortina: A Journey of Tolls, Ink and Ice

MILAN — I’m usually up for an adventure.

But when it came to navigating the roughly 250 miles from Milan to Cortina for the Olympic Winter Games, that sense of adventure got hit with a dose of reality.

As credentialed media, the IOC assigned SportsTravel a hotel in Milan as well as one in Cortina. Or near Cortina, at least. Therein lied the potential adventure that myself and others seeking to visit multiple venues faced: How in the world do you get up there?

For SportsTravel, being in the official IOC system meant we have access to the 2026 Olympics transportation app. By and large, it has proven helpful to navigate large distances even for events within Milan, where the main venues are on different corners of the city’s map. The app allows you to plug in a start and stop point to produce several options of how best to plan your route and how long it will take to complete. Included in that list were options to take public and Olympic-specific transportation from Milan to Cortina, which is one of three mountain clusters for events — none of which are anywhere near each other.

The Milan Cortina Olympic Games transportation app.

To get to Cortina, the app showed I was in for a shocking 9.5-hour journey that included a high-speed train to Venice, another train to get closer to Cortina, a transfer to a bus and then a transfer to a van of some kind to get to my assigned hotel in the quite remote ski town of Pescul, Italy — some 75 minutes from Cortina up a winding mountain road in the Dolomites. While I embrace adventure, the most concerning part of the itinerary was a 16-minute walk between that last train and bus. The specific direction of that walk was not evident. Was I really going to bring even a small suitcase with me on this journey and walk with that piece of luggage 16 minutes in some unknown direction in the mountains? At night?

That’s when I saw the app also offered a “self-drive” option. Curious, I toggled that to discover a drive in a car would be five hours on a considerably more direct route.

Snow Tires, or Not?

That’s how I found myself at an Avis counter at the Milano Linate Airport near my Milan hotel the morning of February 8, signing a bunch of paperwork in Italian to get my Cupra station wagon that I rented to drive to the mountains (apparently the “equivalent” of a Jeep Renegade). One key decision: Did I want snow tires? Looking at the weather forecast, which looked clear in Cortina, I opted out. I live in Colorado. How bad could anything really be up there even if the weather turns?

More Olympics Coverage

Lastly, the attendant told me to return the car with a completely full or near empty tank of gas, a request I don’t recall ever hearing before.

“Nothing in between,” she said.

Did people just return the car empty and then those empty-tanked cars were given to the next person? She had planted a seed that would only grow.

Indeed, my trip didn’t start out nearly as confident as I hoped. I was told my car would be in the nearby rental garage on the fifth floor, spot 150. When I got to the spot, there was no car. But there was a car in spot 151, so I hit the unlock button on the key and sure enough, the back hatch opened. So I put my small suitcase in there to be on my way. Until I wasn’t. As I was loading the back, two very polite Chinese gentleman approached to tell me this was their car.

“That can’t be,” I said. “I just unlocked this car with my key.”

Turns out, they had approached the car behind me at the exact same time and it was their key that unlocked the car. That took us more than a minute to work through but they were right. I eventually tracked down an attendant who searched and found my car, several rows down, apologizing for the mishap.

There was no need to apologize. I was prepared for some odd stuff to happen on this trip, I was under no deadline to get to the mountains at a time certain and I figured that was the worst of it.

But there was more to come.

‘Your Tank is Full!’

Getting into my Cupra, I attempted to sync the car’s dashboard display to my navigation app for the five-hour trek ahead. After it appeared to sync, I figured out how to put the car in drive (tricker than it appeared with an odd flicking device) and off I went.

Almost immediately, everything in the car started beeping. Was I going too fast? Was I out of gas? Was the door open? It was unsettling as I curved my way down five stories on tight ramps and out the garage. That’s when I noticed my app actually wasn’t syncing and I was essentially just driving around the airport with no idea where I was going.

And the beeping. So much beeping. One of the beeps included a red number 30 that kept flashing on the dash. What the heck is 30? Messages also appeared on the dash in Italian with exclamation points, clearly trying to tell me something.

I needed to pull over to get a handle on the situation before I braved the streets of Milan. I found an apartment complex and parked to get everything situated. The first thing I did was figure out how to toggle the dash language to English, so that was a start. And I got my app synced, so all good on that front, too. But the beeping. The car wouldn’t stop beeping.

So I focused on the gas tank. I couldn’t stop thinking about the lady who told me the tank might be empty, or that’s what I believed she said. The car had a dashboard tank display I had never seen before with the number 840 km above it. My first thought: The last person drove 840 km (about 530 miles) before me and this tank is empty. There must be 30 km left to go and that’s why that number is flashing.

I need to get some gas.

So I pulled into the first gas station I passed. The readout on the pump, however, was in Italian. I did my best to figure out what it wanted me to do. But when I inserted the nozzle into my tank, it wouldn’t let me put more than a spurt of gas in there. Thankfully, someone else came in for gas and in desperation, I asked for help. Am I doing this pump wrong? Did I pay correctly? Had I even paid for gas at this particular pump? I was not myself. But the man who approached was calm, friendly and spoke just enough English to help. He reached for the nozzle, squeezed it, and we both watched in horror as gas poured out the tank.

“Your tank is full!” he said, much to his surprise and certainly more to my surprise.

As embarrassed as I could be, I thanked him as he sped off, no doubt with a story to tell his friends and family about the dumb American who tried to put gas in his completely full tank. My dash was telling me I had 840 km more to go until I needed to worry again.

Toll Booth Drama

That drama behind me, off I went. As I drove further, I figured out what the 30 represented on the beeping. My car was alerting me to a new speed limit on the road, reflected in kilometers. In fact, every time I’d enter a new speed limit zone the next few days, I would get a beep and a flashing number. So be it.

Before too long, I hit the first of several toll booths I would encounter along the main highway that would take me most of the way to the mountains. The only problem was that there was no ticket to take and nowhere to pay — just a gate preventing me from proceeding and a button on a wall for an attendant. I had no choice: I pressed the button. Out came the voice in Italian, as loud and distorted as can be through the world’s worst speaker.

“English?” I yelled back.

“Yes, are you stuck?” came a reply.

“Um, yes, I don’t see a ticket to take, I’m not sure what to do.”

“OK, when you get to the next toll, tell them your number is 377. Please remember, 377.”

Suddenly, the gate went up and I went through.

But I was fixated. 377. 377. Must remember 377. Unclear how far until the next toll, I reached in my backpack in the passenger seat for a pen. That’s when I discovered my pen had exploded and my hand was full of sticky, blue ink.

“You’ve got to be kidding me,” I muttered to no one.

With my ink-stained finger, I tried to finger paint “377” as best I could on a piece of paper I had. I then opened up a wet wipe I also keep in the bag just for such emergencies only to discover it had dried up, offering me zero relief.

Words were uttered.

(Side note: It was at this exact point of my trip that I realized my dream to appear one day on “The Amazing Race” with my wife was over. I had a vision of exactly how they would edit my appearance based on the first 15 minutes of this journey and I didn’t like it.)

I was flustered, but I reached the next toll booth about 30 minutes later, recited the number, paid my toll and kept moving.

A Stop in Verona

At about the two-hour mark of my trip — roughly halfway — the journey took me through the charming city of Verona, where I stopped midday to see the ancient arena that will serve as the extraordinary venue for the Closing Ceremony.

The ancient arena in Verona that will host the Closing Ceremony.

I walked around town and saw the 14th Century balcony that supposedly inspired “Romeo and Juliet.” (There even appeared to be a Juliet on the balcony, which — spoiler alert — couldn’t possibly be the case given the way that story ends…)

The balcony that is said to have inspired “Romeo and Juliet.”

I found a pizza place off the beaten path where a man who appeared no younger than 150 years old made me one of the best pizzas I’ve ever had. And I had a cappuccino and rather large pistachio cannoli situation that after every bite I promised would be my last. Before I knew it, the whole thing was gone.

I could have eaten every darn cannoli in town, but I did have to get to the mountains. Nourished and reset, I was off again on the highway to face more tolls. Each toll required a different method of paying, different credit cards they liked and one that was only cash, which thankfully I had in case of emergency. Each toll booth caused a slightly greater degree of angst for me and my ink-stained hands not knowing what to expect and what card to pull. But I got through them all and then took a hard left turn into the Dolomites for my final stretch.

The toll plazas that caused all kinds of angst.

Up and Up (and Up)

I had seen the map before I left and I knew this last part would be tricky on a winding road. Man alive did that road wind! For about an hour of S-shaped turns, I pushed that Cupra higher and higher, the mountains getting steeper and steeper and the views more and more stunning with each turn.

After many turns, I arrived in Pescul at the Hotel Lorenzini Ski, a pretty mountain lodge near a ski resort. I walked into the front door ready to take a load off after a comical and unsettling journey only to find no one there. I rang the bell at the desk. No answer. I rang it again. No answer. I called the hotel phone line only to hear the phone at the desk ring, which only made me chuckle. It had been a long day — a little over five hours since I left the airport — but there was nothing to do but wait. Thankfully, after about 10 minutes, someone came down, apologized in English and checked me in, handing me the physical key to Room 17, which was attached to a large wooden key ring.

When I got to the room, there was a cryptic phrase just to the side of the door: “Its the Truthful.”

I raised an eyebrow. It’s the what now?

I opened the door to a perfectly fine if bare room that had two decorations on the wall. One was a phrase that read: “Wake up Wonderful Every Morning.”

The other was an image of a bunny, which I imagine was supposed to look friendly to a child. To me, it was essentially haunting my every thought as it stared directly at the bed I’d be using — the only item on a stark, white wall. I wanted to make the next morning wonderful, I really did. But this bunny was threatening that possibility.

Getting to Cortina

One reason I chose to drive to Cortina was the unknown of whether the Olympic shuttle that was supposed to depart every 45 minutes from Pescul would actually arrive. In the event it never showed or showed at random times, I liked the notion of being able to drive into town.

At breakfast the next morning (which included an extraordinary display of random meats, some quite heavy for a morning meal), two American photographers also staying at the Lorenzini Ski assured me the shuttles were reliable. It was another relief.

And sure enough, when I was ready to go to Cortina, the small van was there. I got in and it wound its way the 70 minutes further up (and up and up) the road until we peaked and wound our way down (and down and down) to the quaint town of Cortina.

The village of Cortina, a perfect mountain setting for events.

Over two full days there, I took in sliding (luge), curling and alpine skiing, the three main sports clustered in Cortina.

And the ride back each night to Pescul was fine, except one night when a renegade driver managed to shave 25 minutes off the commute — whisking us back in an astonishing 45 minutes that made me question if I’d survive. (At the first turn, I uttered out loud, “Oh boy…” just on pure instinct.) And it wasn’t just me. At one of two stops our driver begrudgingly made on his way to the land speed record, two Italians got off and wished us all “buona fortuna!” with one adding for good measure: “Good luck everybody! I hope you don’t be sick!”

I wasn’t, but barely. Especially since the last 10 minutes included the smell of the van’s brakes burning.

Time To Return

As time went on, I was convinced I had made the right call to drive to the mountains. When I met another photographer at my hotel from Canada, I told him I had driven. He shared that he took the train/bus journey and experienced my nightmare on that 16-minute stretch of unknown. He had waited for 45 minutes in the dark and the cold for a bus to arrive not knowing if it would. “This was the stop,” he showed me in a picture, revealing a small hut surrounded by total darkness. That was enough to convince me I had made the right call.

But I still had to get back to Milan and I was hoping to make it back in time for that evening’s speedskating session.

When I departed the Lorenzini Ski at about 9:00 a.m. on February 11, an inch of snow had settled overnight in Pescul. It was nothing terrible, but I knew from winter driving experience that an inch of snow is sometimes worse than six inches of snow.

My ride down the mountains was extremely slick. Did I wish I had secured the snow tires? Yes, yes, I did. Other than a few very small skids on the ice, I made it all the way down, once again relieved to have that part of the journey complete, but knowing I had all those pesky tolls to navigate on the way back.

This time around, the toll experience was slightly easier but similarly inconsistent on payments. But I didn’t have to remember any numbers, which was progress.

I stopped once again in Verona around 1:00 p.m. and had a fantastic meal at another side-street restaurant. And I had a satisfying espresso and modest-sized ricotta cream cannoli whose only fault was that it was not 10 ricotta cream cannolis.

The final stretch from Verona to Milan was uneventful and I found the airport garage with relative ease, laughing as I passed the gas station from three days back with several dozen kms left to go in my tank — close enough to empty to satisfy that reception clerk. Pulling in around 3:00 p.m., I had made it back in plenty of time to see the events that night in Milan.