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La Piazza Blog & Stories
Guest Stories: Jeff Gair
Stories
September 03, 2025

Guest Stories: Jeff Gair

Stylish male cyclist in Italy riding gear with Enchanted Castle of Neuschwanstein in the background.

Do More of What Makes You Happy: Adventures on Two Wheels

I grew up on the outskirts of Toronto and now live about 100 miles east of Toronto in the Trent River Valley. I have been an avid cyclist for over 20 years—it’s what keeps me sane. I find solace in the open road; when I get out on the bike for a long ride, all the stress of daily life just fades away. They say you can’t buy happiness, but you can buy a bike, and that is the same thing to me.

I did my first cycling tour in 2010 in Newfoundland. I thought, what better way to experience a place than by bicycle? And I was right—it is the perfect way to travel. I was hooked on cycling tours, and I did several tours in Eastern Canada and Vermont over the next few years. In 2017 I made some new friends on a tour in Arizona, and at the end of the tour they told me I was on their list. I wasn’t sure if that was a good thing or a bad thing, but it turned out to be a very good thing. Just a few short weeks later, they let me know they were doing a tour in Tuscany in 2018 and wanted to know if I was interested. I didn’t hesitate to say yes. I had been wanting to try a European tour for some time but admittedly was a little hesitant to travel solo to a country where English isn’t the native language.

Cheerful group of cyclists enjoying drinks at a cozy Italian cafe after a bike tour in Italy. So my first Ciclismo Classico tour in 2018 was Assaggio Toscana, and it was a truly magical experience. I quickly understood why people fall in love with Italy—the beauty of it all, the incredible food and wine, and the people. I got my introduction to Italian hill towns with the beautiful climb to Cortona. I had the pleasure of celebrating my birthday on that trip, and superguide Marcello made sure it was a special day.

Other Ciclismo tours I have done include Puglia, Bike Across the Netherlands, Munich to Verona, and very soon I’ll be biking across Portugal. They have all been incredible experiences. As a craft beer enthusiast, I thoroughly enjoyed the beer culture of the Netherlands and Belgium and talking about good beer with our guide Isacco Colombo. On the last night of that tour, Isacco took some of us to one of his favorite beer bars in Bruges, Le Trappiste Brugge, and bought me a bottle of the rare Westvleteren 12, the holy grail of beers for any beer nerd. It was an amazing way to end another great tour.

I would have to say my favorite tour so far is Munich to Verona with Frank and Dana, and Carlo. Traveling through three countries in a single tour is an incredible experience. From the Bavarian countryside through the Alps to Innsbruck and into South Tyrol and down the Adige River Valley to Verona, the scenery was spectacular. Starting with hefeweizen and helles in Germany and ending with Ripasso and Amarone in Verona.

My motto in life is: Do more of what makes you happy. So as long as I can ride, I will continue to explore this world by bike. I look forward to many more adventures with Ciclismo Classico!

Vibrant Italy bike tour cyclists enjoying drinks at an outdoor café, showcasing scenic bike rides and relaxed stops on an authentic Italian cycling adventure.

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