“Buona sera, signora,” a cheerful white-haired man greets me as he takes my luggage and shows me to my sleeper cabin on the Espresso Cadore. After the train departs Roma Termini station, I head to the train’s bar car to grab a glass of prosecco to kick off my trip to the Dolomites—to ski on Italy’s famed Olympic slopes.

As I pass through the red plush-carpeted hallways, I look back at a time well before my first experiences taking trains in Italy 20 years ago while studying abroad in Florence. I pass photos adorning the walls of passengers decked out in 1980s and ’90s colorblock ski suits, skis-in-hand as they emerge from train cars and step out onto fresh snow.