Days 1 and 2 were travel days. Getting from Toronto to Tirano took roughly 14 hours. Flight to Milan, train into the city and then another train into the mountains to Tirano. Here are some notes from the road:

First frustration of the trip; I bought a train ticket at the ticket desk. The girl told me where to go to board the train. Once on the train the security agent told me the ticket was not valid so he wants me to pay an additional 9€ for another ticket!! Apparently the ticket needed to be validated before boarding.

Feels very much like a shakedown as almost every person on this train car is in the same situation as me – unless they speak Italian. Strange that the folks selling the tickets don’t tell you to validate the tickets. And also strange that the security guy only takes cash…

I said I only had VISA and he said he’d be back. He never came back.


Milan Stazione Centrale is a busy station where everyone smokes. And no one seems to give a damn about anyone else.

I managed to get my ticket to Tirano, an awesome pizza, an average espresso and some sparkling water, and then get on the train all in under 20 minutes and for less than 20 €. Woo hoo.


The train ride from Milan to Tirano is pleasant with great views of the mountains and Lake Como. And as my wife reminded me, this is Clooney-country. He has a villa along the western shore. I should’ve have asked him if I could stay there seeing as he’s currently in Toronto at TIFF.


I was listening to CBC Radio last week. They were interviewing an ASMRtist. Someone who creates art that gives you that tingling feeling of being relaxed. Check out some of the videos on YouTube to better understand it… For me that happens every time I’m lying in the dentists chair but that’s about it. But sitting on the train, reading a great book, going on this adventure that’s going to be filled with physical and mental struggles, I’m feeling it.


Settled in to my hotel and out on the town looking for dinner. It’s 5:15pm. Saturday night. There’s a wine festival happening. And dinner time doesn’t start until after 7. So it’s an espresso and then some vino. And then dinner.

I’m worried that once the sun goes down the temperature plummets. The local are all in fall jackets with scarves. I’m in a golf shirt. Right now I’m overheating. But in about ten minutes the sunshine will be blocked by the mountains. More later.


We met our tour guides – Tom and Valentino – along with the other travelers in the hotel lobby at 7. It’s fun to see each person trying to rank themselves relative to the other riders. Who’s faster than me? Who’s can I easily beat? Am I in over my head? Overall it appears that we’ve got riders spanning the spectrum from “this is well beyond my skill and strength” to “I do these kinds of rides every day”. I’m not sure where I fit at this point. Likely towards the faster end but I’m hoping to really soak in the sites, sounds, and tastes without contemplating Strava segments. We’ll see how strong my resolve is once we clip in!

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