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The best day trip from Florence, Italy, is on a bike to Siena

We wanted to bike in the Tuscan hills and we wanted to take a day trip to the medieval confection of a town. Research uncovered a way to do both at once.

The Duomo in Siena is one of the most important and magnificent Romanesque-Gothic churches in Italy.
The Duomo in Siena is one of the most important and magnificent Romanesque-Gothic churches in Italy.Read moreWikimedia (custom credit)

The Italian man puffed his way up the narrow road — literally.

His hands clutched his handlebars, leveraging them for power as he cycled uphill. That left only one place for his cigarette: between his lips.

He smiled in greeting as we passed. Headed in the opposite direction, I had just crested the hill and my speed was picking up. On this sunny Saturday in spring, I had already coasted past fields of gnarled olive trees, seen a pheasant scamper into the grasses, breathed in Cypress-tinged air — and encountered scads of Italians in skin-hugging bike shorts zipping across Tuscany.

“Italians are crazy for bikes,” our guide, Marco Vignoli, told me before I set off. An Italian could be broke and still wouldn’t hesitate to drop $5,000 on a road bike, he said with a shrug.

Perched upright on a comfortable hybrid bike, I began to understand: It's the best way to experience the countryside.

When planning a five-day stay in Florence, my husband and I had two side trips in mind. We wanted to bike in the Tuscan hills and we wanted to visit Siena, a medieval confection of a town with the dramatic oval-shaped Piazza del Campo at its center.

My research uncovered a way to do both at once.

"How about if we biked from Florence to Siena?" I asked, with my laptop propped open.

I’d struck on the idea after my online journey led me to the favorably reviewed I Bike Tuscany. The Florence company offers a range of cycling excursions in Tuscany and beyond, from private, guided multiday adventures designed to a rider’s specifications to small-group day trips, including a 20-mile Florence-to-Siena ride.

A different trip, however, had caught my eye and sounded even better — by 7 miles. Dubbed “Florence to Siena Soft,” it begins with a van ride to a hilltop village, eliminates all but one long climb and covers a breezy 13 miles.


The morning of our ride, we fortified ourselves with a big hotel breakfast and then headed to the meeting point. (The company couldn't pick us up because our hotel was in a pedestrian-only zone.) We knew we were at the right place when we saw a van with bikes on its racks and a lean Italian looking for us.

In March, the biking season was young, so we had a double treat: No one else had signed up, so our group tour became private. And our guide turned out to be the owner of the company, Vignoli.

A former cycling racer and longtime biking guide, Vignoli turned out to be a charmer, and not just in that iconic Italian gentleman kind of way. He splits his time between Florence, where he grew up and where his mother still lives, and the Los Angeles area, just a few miles from where my husband and I used to live.

We spent the ride to the starting point discussing his favorite biking routes from Los Angeles’ Brentwood section to the Pacific Ocean. He offered restaurant suggestions in both Siena and Florence. Tony Bennett crooned on the van’s speakers.

After a 45-minute drive, Vignoli dropped us at a coffee shop in Castellina in Chianti, a golden-hued stone village that seems to have sprouted from the hilltop eons ago. We walked down its winding main drag to a farmers market with commerce intended for locals, conducted by vendors who did not speak English.

We were tempted by cheeses, salami hanging overhead, and heaps of vegetables. Using rudimentary Italian, I bought a bag of mixed dried fruit whose names I mostly did not recognize and bottled herbs from a farmer shading himself with a yellow umbrella.

After shopping, we rejoined Vignoli at the coffee shop and headed to a parking lot, which was large and open enough for us to try out the bikes before starting our journey. Vignoli told us that he’d meet us at every stop and turn along the way and then drove ahead.

Soon, he was flagging us down at a cluster of stone buildings and led us into a sleek bar for a wine tasting in Fonterutoli, which bottles Chianti Classico and other wines. Yes, it was just 10:30 a.m., but the sips were delicious.

Our next stop was a scenic overlook, where Vignoli checked on our water supply. He later waved us on at a corner and touched base before our only significant hill. "No racing; the hill is long," he warned.

I took the gears as low as they would go, and worked my way to the hilltop hamlet. There, I rejoined my husband, who'd already finished the ascent, and Vignoli, who gave me an enthusiastic high-five. From there, he assured us, we didn't have far to go.

By the time I next saw him, I was ready to quit, my legs feeling a bit like jelly. But they had enough power left for a walk through Siena.

We rode the van to the outskirts of town, made a plan to meet Vignoli at the same spot in three hours, and tracked down lunch in the city; we'd set off from Florence at 9 a.m. and made it to Siena by 1 p.m.

We marveled at its duomo, ate heaps of pasta, and enjoyed a scoop of guilt-free gelato in Piazza del Campo, along with loads of other tourists. Siena was beautiful.

But after our cycling in the countryside, where we encountered biking Italians, but few others, Siena felt crowded.

We were content to decompress during the ride back to Florence, nibbling those mysterious pieces of dried fruit and watching the landscape pass by at a van’s pace. We’d already seen Tuscany at the best pace, by bike.