Guest Stories: Trent Davis

How Ciclismo Classico Turned My Love for Cycling Into a New Life in Europe

Twenty years ago, I joined a bike tour in France with the Boston Ski and Sports Club. While the scenery was stunning, the experience fell flat. The group was split between hybrid and road bikes, and we rode at very different paces. I was left feeling disconnected—and a little let down. Still, I loved the places we visited: charming villages, peaceful lakes, and picturesque towns that stirred something in me. I knew I wanted a “re-do”—but with a more professional company.

That’s when I found Ciclismo Classico.

My first tour with Ciclismo took me through Toscana, and it was wonderful. I rode alongside cyclists who matched my pace and spirit. The guides were attentive and organized—taking care of every detail. The villages felt like stepping into a foreign film—quaint, antique, full of soul. We visited wineries, of course, and even toured an olive oil farm using a 500-year-old stone press. One evening, we made our own pizzas outdoors under the stars. One of the most memorable touches? A picnic lunch set at the very spot where the Mona Lisa was painted.

The next Ciclismo experience brought me to Venice. That was my first visit there, and I was deeply moved by the uniqueness of the city. As I entered Piazza San Marco, following the group with no expectations, I was suddenly overcome. The basilica. St. Mark’s Bell Tower. The statues. The Bridge of Sighs. It all stopped me in my tracks. Later that evening, it happened again—this time it was the sound of opera drifting through the narrow streets. It was haunting, beautiful, and unforgettable.

Whether in Italy, Switzerland, and France have been uniquely memorable. Cycling with new, like-minded friends; multilingual, fun guides; the gourmet meals and picnics; European wines and pastries; and interesting, posh hotels are what we’ve come to expect with Ciclismo.

Ciclismo opened my heart to Europe in a way I never expected. So much so, in fact, that I eventually decided to move to Spain. Today, I live on the coast, still riding, still exploring—still grateful for the path that got me here.