First Sunday in October takes place the vintage (pre-1987) bicycles, accessories, and clothing L’Eroica event that starts and finishes in Gaiole. It was still May when I freewheeled into Gaiole from the junction that a couple of days earlier I turned right on toward Radda. This time, I headed south to Gaiole and on to Siena.

The weather was still horrible, drizzling as I pedaled to the top of the ridge above Cavriglia. It was pouring as I pushed off downhill to Gaiole and I had to stop and hide under trees at the side of the road for over thirty minutes. When the rain let up, I pedaled into Gaiole, stepped in the church Chiesa di San Sigismondo and cursed the weather.

At last, an hour later, I could continue with my second climb of the day toward Castello di Brolio. The sky cleared, fog lifted, and first rays of sun soon appeared. The parking lot at the castle winery was full with tourist buses arriving for wine testing of the original Chianti recipe and well-known wine label.

As the weather improved, beyond Brolio began a spectacular downhill that only got more incredible with every kilometer. The panoramas looking west and south were sweeping, the landscape lush green and undulating. I rode past many wineries and through small hamlets, the scenery so Tuscan that I disregarded the rain that started up again, depositing me at the bottom of a climb toward Porta Pispini, the southeastern gate into Siena.

From Cycling Tuscany & Umbria

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