In Tuscany, I learned to roll with the ups and downs on a cycling adventure | Canada Voices

My Italian cycling guides were fond of saying “allora ...” This multipurpose Italian opener relies on tone and body language to interpret it, like “so” or “well” in English. What you hear after “allora” can be good news or not what you had hoped to hear.

It became my favourite souvenir of the trip. So here goes: Allora … there is a story that I want to tell, and another that I need to tell. I also wonder if my cycling adventure in the Tuscan countryside was more memorable because it didn’t go as planned?

Long-distance cycling was never in my wheelhouse, but my friend loves it and has bugged me for years to give it a shot. How many times can you turn down a good friend? So last October, when a chance came up to explore the rolling hills of Tuscany on two wheels, I looked into it.

Butterfield & Robinson runs active, superluxurious trips around the world. The 60-year-old Canadian company was one of the first in this rarefied world of small, bespoke group tours. Tuscany is one of its most popular destinations and connections there run deep.

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After a day of cycling and eating well at every stop, where locals would share their love of olive oil or wine or local legends, the night’s lodgings always blended historical wow and five-star delights. Even better? My friend could ride a carbon-fibre performance road bike and I could try to keep pace on an e-bike.

But you still have to train, Irene said. During our (almost) weekly 22-kilometre rides in Toronto during the three months leading up to the trip, I was schooled about toughening up my “saddle area.” Wearing padded cycling shorts was not enough – I had to ditch the underwear. And did I slather on the anti-chafing cream she’d given me? Irene was pleasantly relentless on the topic, so I pushed squeamishness aside to harden this sensitive spot. Dreams of Italian food and wine in the coming Florence-Chianti-Pienza-Cortona adventure helped greatly.

We arrived in Florence before the tour started. Late October is a good time to visit this living museum of a city, as it was busy with tourists but not packed. Our hotel – Tivoli Palazzo Gaddi Firenze – was right in the centre.

I was charmed by its grand interiors, where modern colours accented historic ornamentation and where Pilates classes are held in a ballroom under 18th-century frescoes. The rooftop bar allows you to watch the sun play on the famous Duomo, and note how the cathedral’s ochre roof and cream, pink and green marble glow gorgeously in the late afternoon.

We met our B&R guides and the rest of our group the following morning. Marella Iodio picked us up in a comfortable van to bring the group – all six of us dressed to ride – to a countryside villa. Tall iron gates swung open and we walked down a cypress-lined drive to meet our cycling guide Luca Cedroni. He welcomed us with espresso and pan co’ santi, a local raisin and walnut bread.

When he walked us to our bikes, I noticed his enormous, extremely defined calves and wondered if these Tuscan hills were going to be more than I bargained for. I nibbled my bread and listened to the rundown on the day’s ride as he pointed to a map he had drawn in grease pencil on the window of the support van.

Today would be an easy start through Chianti, he reassured us: 17 kilometres until lunch, with one wicked valley in between. Then, three kilometres after lunch till we reached our hotel. It was inside a 12th-century castle. I already couldn’t wait.

Cedroni made sure us e-bikers understood one thing: “You have to pedal to get a boost up the hills.” Iodio pointed out the route map on a phone attached to the handlebars. “It’s easy, no?” she said. “Follow the blue line and make sure it turns red.”

Irene busied herself attaching her own shoe-clip pedals to B&R’s sleek bike. I noticed she ditched its padded seat cover. I cherished mine.

“Andiamo!” Cedroni cried: Let’s go.

As we all found our stride, the group soon split into pairs along the two-lane highway. The sun was strong and we pedalled past olive groves and old stone churches, through the atmospheric streets of medieval villages and past vineyards that stretched out for days, leaves golden and grapes harvested. Irene and I kept stopping to take pictures. It was hard to believe we were here at last.

I chugged up hills – priding myself on never using the bike’s easiest “turbo” mode – and relished racing down. The wind whistled through my helmet and whipped the laughter right out of my mouth. Had I ever felt this free?

When we arrived on shaky legs to lunch, La Fattoria was full of families sharing roast pig on this Sunday afternoon. Our group were the only tourists. Here I had my first Tuscan steak: bigger than my fist, flame-grilled just enough to take the moo out and served on a cutting board, flaky salt the only accompaniment. I inhaled it. Then picked at the family-style plates of wild boar pappardelle, salad and the region’s traditional unsalted bread. Cedroni told us the bread’s history (baked this way to avoid salt taxes in the Middle Ages) as Chianti reds were poured.

There were still more hills and dales to conquer before day’s end, and one heart-in-your-mouth downhill switchback. But the beauty of a B&R trip is that our hotel was the five-star Como Castello del Nero, surrounded by vineyards with an enormous spa, and that was motivation enough.

Cycling was a new way for me to explore a destination. I enjoyed the daily exercise and camaraderie of exertion our group shared. Irene and I might cycle together or power up inclines solo when there was no energy left to comment on the stunning row of cypress trees to the left or the rolling vineyards and villas to the right. I learned a lot about my own endurance, too, even when I thought there was nothing left and I wished I had smeared on more of that Chamois Butt’r.

I also learned that when Cedroni reassured us that our day’s ride was “flat,” he really meant “Tuscan-flat,” which wasn’t really flat at all.

One day, the three of us were way behind the rest of the group, so Cedroni asked if we wanted to take a detour. Of course! We followed him up one more hill into the pretty medieval village of San Donato. The stone streets were quiet and we stopped to fill our water bottles at an ancient fountain. Cedroni explained the village was often a prize in the old battles between Florence and Siena. The extra exertion was worth it and this off-itinerary bonus gave us something to humblebrag about at dinner.

When rain wiped out plans to ride on the fourth morning, Iodio and Cedroni drove us to a 14th-century Benedictine monastery where monks still live and work. We walked through its frescoed corridors and explored the forested grounds. When the weather cleared, Cedroni had our bikes ready to go.

Now in Tuscany proper, the landscape rolled luxuriantly and gloriously on either side of the road. On one descent, I had kicked out my feet and coasted with joy. Saddle-sore no more, I felt like a kid again.

Allora … now this is the story that I need to tell, because when I fell off my bike the next day, I learned that good guides know how to pivot, and quickly.

I was coddled and cared for. I never felt like a liability that threw their planning out of whack. Iodio kept me company and advocated in Italian for me in the ER. And the fellowship that our guides fostered between their guests paid off too. I was restored with a motherly hug when still in shock, and the pharmacists in our group had expert painkiller and icing instructions. That same night, I was on the phone with a hotshot orthopedic surgeon in Britain since a fellow e-biker wanted to make sure I had the best medical advice.

Accommodations for my injury were seamless, not strained. While I could no longer ride, I could walk. Iodio and Cedroni gave me time to explore Pienza on my own (I had missed the tour), made sure I knew the European name for Tylenol and arranged for a driver take me (and everyone’s luggage) to the next stop. In Cortona, I got to explore more of the hilltop town with a local guide since the cyclists took longer than expected. It was a tough three-kilometre climb on the bikes and I can’t say I missed that too much.

Cycling through the Tuscan countryside helped me get to know its history and beauty. Being injured taught me more about the people there, through the help and kindness I received. (Wearing a sling, however, does not get you a pass in Cortona if you order a coffee by its Spanish name instead of Italian.)

Eventually, I found a way to drape my scarf over the sling and dressed up for our last dinner. We were staying at a hunting lodge that dated back to the 15th century and had ties to the Medici family. Villa di Piazzano’s restaurant was full of regional favourites such as prosciutto toscano, pecorino cheeses and hearty red wines. Good food, lots of laughter and even better wine will cheer anyone up.

Allora … I was still enjoying myself. I wasn’t ready to go home.

If you go

Butterfield & Robinson’s six-day, five-night Tuscany Wine Country biking trips have regularly scheduled departures June through October. Rates start at US$6,995 a person. Self-guided trips start at US$6,395 a person. butterfield.com

Tivoli Palazzo Gaddi Firenze is located in the old town, less than a 10-minute walk from the train station. Make sure to order a drink in the lobby bar inspired by poet John Milton, who began writing Paradise Lost while he was a guest here centuries ago. Rooms start at €300 ($479). tivolihotels.com

The writer was a guest of Butterfield & Robinson and the Tivoli hotel. Neither reviewed or approved the article before publication. Stories are based on merit; The Globe does not guarantee coverage.