Giacomo Bernardi

Guide

At The Cycling House Since: 2025 Hometown: Tuscany, Italy Trips Working:

Guide

Giacomo Bernardi

I’m Giacomo, born and raised in Siena, Tuscany, where cycling, great food, and rolling hills are part of everyday life. I’ve been on two wheels since I was a kid, especially during our long summer holidays. After years of playing soccer and swimming, I got back on the bike seriously around age 30.

Working as a private driver brought me into the world of cycling tours, and that’s how I met Andrea, who I’ll always thank for introducing me to this amazing TCH family. One thing led to another, and before I knew it, I was guiding rides myself, learning from incredible guides, and sharing unforgettable experiences with riders from all over the world.

I’ve always been more of an off-road rider, gravel is my true love (after all, I live in Tuscany, home of Strade Bianche and L’Eroica), but lately, I’ve also been enjoying smooth tarmac and long road days. I’ve always loved outdoor sports and spending time in nature, hiking, skiing, or just being outside, taking pictures of landscapes and people.

I live in Siena with my wife, Paola, and our two wonderful kids, Lorenzo and Giulia, who already love their little bikes. I guess it runs in the family!

What's the best thing about working at The Cycling House?

It feels like riding with a bunch of old friends, a team that gives everything to make guests feel at home while having the time of their lives. Every ride, every dinner, every laugh… it’s a mix of joy, fatigue, and friendship that’s hard to describe unless you’ve lived it.

Do you have a favorite ride?

The Dolomites, especially the Sellaronda loop. I grew up skiing there, and riding those same mountains in summer still gives me chills (and sometimes sore legs too!).

What is the most memorable day you've had on the bike?

There are too many to count, but some of the most special are the ones close to home, riding through the Val d’Orcia, sharing a glass of Chianti with guests, and listening to their stories about life and cycling. That’s when I realize how lucky I am to call this my job.

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