The next morning I was part of it. After fitting the bikes and distributing panniers, helmets and gel seats (soon to be my new best friend), our guide Guido led us on the first stint of our cycling holiday – a speedy downhill stretch, past grape-heavy vines and tastefully renovated holiday homes. It didn’t set the tone. After lunch came a gruelling ascent that had me cursing my lack of pre-trip training and letting the push-bike live up to its name. Perhaps I should have realised that a cycling tour of hilly Tuscany would never be an easy ride.

Still, there was plenty to urge our weary legs on, not least the chance to get up close and personal with the Chianti and Siena regions. From isolated farms and dusty churches to vineyards bursting with juicy, red grapes – biking through the countryside meant I glimpsed corners of Tuscany I’d never otherwise have seen.

For most of the trip we were treated to perfect cycling conditions: warm, with a light breeze. But as we made our way to Monteriggioni, a pretty lookout post built to alert Siena to war-mongering Florentines, the clouds began gathering. It started to rain just as a member of our group discovered a broken spoke and puncture. While our guide earned his euros the rest of us were left to wander around the small town. Through a restaurant kitchen doorway we watched a woman slice a sheet of pasta into neat squares. With our collective mouths watering, the lunch stop was brought forward and when we finally emerged, stomachs full of home-made ravioli, the sun was shining once again.

Exploring the much-disputed land between the rival cities of Florence and Siena, we’d been immersed in lush countryside broken by clumps of trees, neat vineyards and scattered olive groves. As we left Chianti for a part of the Siena region known as Crete the scene changed dramatically. Tilled earth stretched away from the roads, the furrows flattening into sweeping waves that glinted silver in the sun. Each way you looked the setting seemed too good to be true, with a lone farmhouse or elegant line of Cyprus trees that might have been air-brushed in.

As we puffed our way up to the Abbey of Monte Olive to Maggiore, a sign declaring “Pecorino a vendito” (cheese for sale) seemed a good place to stop. Our cries brought an elderly woman and her son out of their house. Smiling hello, they opened up shop and while the man went to the trouble of putting on an apron and washing his hands the woman prodded each sturdy, yellow wheel of pecorino (cheese made from sheep’s milk) exclaiming “fresco” with each poke. We left with a hefty portion of the mild, white cheese – fuel for the hill that stretched ahead.

It got us to the top and we trundled into Montalcino to be rewarded with the best-looking town so far – and the competition had been stiff. Despite its grand castle, crest-studded tower and medieval streets, Montalcino has an unassuming air that makes you feel at home immediately.

Or perhaps it was the free wine-tasting at a bar overlooking the Piazza del Popolo.

When the freebies ran out we ducked into the nearby Enoteca Osteria Osticcio. At a table by a huge wall of windows, we sipped the area’s famous Brunello as the sun slowly dimmed the ochres and sage greens of the valley beyond. Tomorrow, en route to rival Brunello producer Montelpulciano, I would be part of the view once again, but for now I was happy to admire from afar.

» Amy Adams travelled to Tuscany on a six-day cycling tour with the Chain Gang (+44(0)1392 66 22 62;

Grape expectations
Say what you like about Hannibal Lecter, he had good taste in wine. While you might want to skip the fava beans and human liver, it would be a crime to leave Chianti without getting to know the wine. Our trip took us through the heart of the region – where the wine Chianti Classico is made – to key wine town, Greve-in-Chianti. At Le Cantine, the biggest enoteca in Chianti, an unusually fresh-faced sommelier, Marco, explained the differences between Classico wines and the more experimental Super Tuscans. He also introduced us to the “King of Tuscan wines”, Brunello di Montalcino, and the delights of a machine that can fill your glass with 18 varieties of wine at the push of a button.