#96. Dolomites (Thursday, June 26, 2025)

What was your best day…of a trip being special just because of how normal it was?

As physically impossible as it is for ten days in the sequestered, scenic Northern Italian mountains to be uneventful, this summer trip to the Dolomites was as by-the-book as it came. And at that point in my life, that was exactly what I needed.

I won’t claim that I was facing any kind of real crisis at this point. But in the months leading up, I had been dealing with the carry-over emotional effects of a standard personal situation that was nevertheless unprecedented for me. And this translated into some uncharacteristic frustration at work, as well as falling mentally off track with my previously disciplined novel revisions (#121). A mental reset was nowhere near necessary, but it was definitely welcome.

I went with my mother, my brother, and his girlfriend Lysa (for the first half¹). And for each day, I only have one real highlight worth sharing:

• Sunday flight: A flight delay forces us to solve a real-time optimization problem between a dozen potential stopover cities to get to Venice on time. On the positive side, it also means our layover in Toronto coincides with the second half of Game 7 of the NBA Finals, which I watch over beers with some random guys at the bar.
• Monday landing in Venice, castle hotel to the north: What stands out to me during the two-hour drive into the mountains is how few truly empty stretches of highway there are. It feels like every ten minutes, we come across a different picturesque village with its own community and distinct character.
• Tuesday in Cortina: This small town is jointly hosting the upcoming 2026 Winter Olympics with Milan, so as we take the gondola up the mountain, I can see the long network of bobsleigh tracks in a state of alarming half-completion, seven months away from competition.
• Wednesday, Tre Cime: This is our one mountain hike on the trip that’s actually semi-dangerous. There’s a long stretch where we’re walking on a narrow path along the side of a cliff, except the path itself slopes slightly toward the vertical drop a few feet away.
• Thursday, Tyrol: We have lunch at this legit, extremely pricey² farm-to-table restaurant (inside a farm) near our Cortina hotel, where the grass-raised beef and the special cream (delivered on a rock) stand out. At night, we get stuck waiting in a tunnel for two hours because of a major lightning storm—which thankfully starts before our thirty-minute trek up to our mountain hotel.
• Friday, up in the mountains somewhere (my mom did all the planning): Here, I’ll note that driving in the mountains in Europe is very much at your own risk. The roads are extremely narrow, it’s all sharp turns where you can’t see oncoming cars until a second or two before, the drivers don’t bother slowing down, and there are tons of bikers that go half the speed and you can’t pass unless you’re willing to risk a head-on collision.
• Saturday, another Tyrol town: We get up at five a.m. to walk across this long series of fields and valleys to get to this special sunrise view spot. It’s not that special (to anyone but my mom), but the arduous, scenic, likely unnecessary journey to get there forces us all to recognize it as such.
• Sunday, rest day: On our hotel balcony this afternoon, my brother, mom, and I have our one serious conversation of this trip, when the aftermath of my “personal” situation gets dissected. But before it gets too serious… the largest hornet I’ve ever seen flies by us and forces us inside (ending the session).
• Monday, down to Malcesine: After an afternoon of doing cannonballs at the beach, and after a giant wasp derails our evening hotel pool plans³, my brother and I just have beers for two hours on the terrace with a rare mature-but-casual conversation about our jobs: solving the mysteries of hedge fund strategies (#121), and estimating bone cancer probabilities from X-ray imaging.
• Tuesday, through Verona, to Venice: It’s my first time in Venice, and I find the narrow canal system integrated with the smaller side streets pretty cool; even cooler than the chaos of speedboats and water taxis and rip-off gondolas on the main waterway.
• Wednesday, half-day in Venice: The extreme heat causes my mom and brother to bail early in the afternoon, though I was fine since I had spent half the day inside exploring the Doge’s Palace and immersing myself in the artifacts and architecture from centuries back when this little island city was its own powerful civilization.

Between those mostly ordinary adventures, spending an extended stretch in the mountains put me into a strange baseline state. Waking up every morning to a different high-elevation backdrop made my whole life feel slightly removed from the normal plane I had been occupying at home.

And, during this particular period, that slight separation was all I needed.

1. Before she took the short train to Germany to spend the rest of the vacation with her family.
2. The price is highly dissonant with our experience when we visited the evening before. No one was around, even the cows. Then, suddenly, a shirtless guy in a towel emerged from a one-story shack outside the farmhouse asking if we wanted to book a reservation for tomorrow.
3. This one only triggers my brother’s terror—he’s the one with the actual phobia.