The sun shines differently on Tuscany! It illuminates the meandering back roads over the cypress-lined hills leading to a sea of Chianti vineyards. So engulfing, time appears to stop or perhaps rolls backward.

The bicycle changed transport and further connected Italy’s villages and cultural centers of Florence and Rome. They helped locals build a nation in the Industrial era and Tuscans to reach their neighboring villages. Once only locally-known dishes, olive oils, and wines spread abroad.

Cycling through these villages today, you slowly connect the dots of the past with the present, the wines with their laborers, and the food with the earth. See a vineyard, stop and put your foot down to smell the Tyrranian air blowing over its rows of vines, or spot a local smile, take a break to shake his hand and hear his story.

Local in Monteriggioni

Spot a local smile, take a break to shake his hand and hear his story

Plan a week’s trip of South Tuscany and Val d’Orcia and cycle through Tuscany’s countryside pedaling through time.

The rolling hills south of Florence towards Siena and Tuscany’s border with the Lazio region flow like a sea of green and golden waves. A challenging hill rewards you with a breathtaking view and descent to another famous wine valley. Cyclists here call these efforts and rewards “mangia e bevi” or “eat and drink.”

The Crete Senesi and the neighboring Val d’Orcia, south of Siena, provides a proper taste of Tuscany. The lunar-scapes of clay producing famous white truffles span to the green hills dotted with vineyards yielding Sangiovese and Trebbiano-based wines, and the Brunellos from Montalcino.

Cycling on the road to Siena

Cycle through Tuscany’s valley pedaling through time

Often only the sheep passing in the meadows break the silence in the air. Siena sits off in the distance, to the south the sun shines on a lonely tree perched on a hilltop and Asciano, Buonconvento and Montalcino cradle the lands below. The road leading out of Asciano, wraps its way through Etruscan and Roman settlements. To the south, you find the Abbey of Monte Oliveto Maggiore. Its red bricks stand out above the grey-blue Crete hills. Beyond a fish pool, the Abbey holds some amazing, yet relatively unknown, wooden inlaid work by Fra Giovanni da Verona.

Gravel paths once walked by Saint Francis and small farm houses or “podere” lead towards Montalcino in the Val d’Orcia. The valley itself is not as well-known as Montalcino, but it holds such value that UNESCO named it a World Heritage Site. On any given day, you could be joined by a fellow cycling tourist or a local pedaling on his way to the next farm between Pienza and Montalcino. The roadside transitions from grain to sunflowers to the renowned Brunello vineyards.

Montalcino sits on a hilltop protected by a wall. Tucked in its streets, you can find several small restaurants to park your bike, lunch and reflect on the travels. The wine, of course, will come from the famous vineyards like Biondi Santi and Il Palazzone. These dark and full-bodied Sangiovese wines from the nearby farms some of Italy’s best known and most expensive wines, but a deserved treat on any Tuscan tour.

Val d'Orcia

Val d’Orcia, south of Siena, provides a proper taste of Tuscany.

The rewards are endless after a day cycling. Italy, and especially Tuscany, prides itself on food and hospitality. Several farmhouses-cum-hotels dot the landscape between Montalcino and Montepulciano. Once near, you will be pulled in by the smell of a ribollita – a Tuscan vegetable and bread soup – or a wild boar cinghiale ragu topping fresh pasta. Conversation may vary from the villages visited to the roads cycled to the locals met. Do not expect any sort of fast food because dining here is like the endless long and slow rolling roads of Tuscany.

A perfect vacation for the cyclist looking to discover the colors and flavors of Tuscany.


“Ribollita” is a Tuscan vegetable and bread soup

Article by Gregor BrownTravelPostBlog.com