Our Bike Routes

Biking in Tuscany, a refreshing holiday or short break, visitors can reward themselves or their family or friends with. Cycling up and down the immaculate countryside, through hills and valleys, inhaling the fresh air, having a healthy and enjoyable workout, meeting up with old friends and new acquaintances, probing antiquated towns, ruins, spas and vineyards along the way are all part of the week-long bicycling holiday we offer.

This 6-day bicycling trip in Tuscany has been designed by an experienced and local biker, who has been cycling through the Tuscan countryside for the past two decades.

Day 1 - Bicycling Across Hilly Montalcino

On our first day of our biking tour, we cycle through the Tuscan farmland and cover the famed town of Montalcino, where we will take steep pathways passing through wine estates, including the renowned Brunello d Montalcino, olive groves and the Etruscan (ancient Italian) remains.

Montalcino and its surroundings are hilly and noted for its spectacular views. The cycling ride on road bikes will be refreshing and bracing as we inhale the mountain air and revitalize ourselves.

Lunch at a local restaurant located near the walls does add a genuine Tuscan flavor as the appetizing food will strengthen us to continue with the rest of the journey. Covering about 30 miles a day we will retreat late in the evening, to a beautiful 14 the century villa and relax by the pool or in the garden, and drink a glass of wine and enjoy the rest of the day.

Did you know?
Montalcino borrows its name from a species of oak trees that previously engulfed the Tuscan terrain. The very lofty spot of the region offers our bicycle tourists some spectacular views over the Asso, Ombrone and Arbia valleys of Tuscany, scattered with silvery olive plantations, vineyards, green pastures and rural towns. Even the foothills are towered over by considerably productive olive groves and breathtaking vineyards.

Day 2 - Val D'Elsa, The Seat of Tuscan Arts

Bicycling through the charming countryside amidst the mighty oaks, silvery beeches, Cyprus trees, lush chestnuts, the ubiquitous olive groves and the not-to-be-missed natural rivers and brooks as we explore the beauty of Val D’Elsa is what comprises the second day. As we explore the large river basin or valley of the Elsa, we will wade through many fascinating little towns and villages.

Halting at a town along the valley, we will have an ingenuous lunch brimming with local Tuscan delights. After an edifying meal, we will resume pedaling along the ancient route of Via Francigena through Colle.

After covering a distance of nearly 30 miles we will once again retreat to your home base, the Villa.

Did you know?
"Colle Val d'Elsa" literally translates into "Hill of Elsa Valley", where "Elsa" is the name of the river-stream which intersects it. Val D'Elsa is world-renowned for crystal glassworks, and accounts for 15% of global art production, mainly produced in the industrial lower town.

Day 3 - Bicycling Across the Fortified Monteriggioni, Tuscany

Elegantly following the natural outline of the hills and exploring the walled-city of Monteriggioni and its all but perfectly intact fortifications that reflect its medieval heritage are the main focus of our cycling tour for the third day. As we embark on our road bikes, weaving through flatlands and slopes, we reach this culturally rich city.

After a characteristic local lunch at this small but visitor-friendly town, we cycle away to sight-see nearby places including an ancient monastery, and a meticulously restored castle circled by vineyards and olive groves, which feature most of our carefully thought out biking routes.

We return to your villa and use up the final moments cycling through the natural woods and tree plantations amidst the villa.

Did you know?
The literary great, Dante, a Tuscan native himself, was so inspired with the outline and shape of Monteriggioni that he used it as an analogy for one of the rings of the inferno; he depicted it as a “ring-shaped fortress whose circling walls are crowned with towers” in his epic poem ‘The Divine Comedy’.

The town is a featured locale in the popular video game Assassin's Creed II and once again highlighted as a backdrop in the game’s 2010 sequel called Assassin's Creed: Brotherhood.

Day 4 - Bike Touring in Siena, Tuscany

Visiting Siena, a Tuscany hill town designated as World Heritage Site by UNESCO, is also an integral part of the tour. Halting for lunch at unusual and popular local taverns, restaurants and trattorias particularly at the shell-shaped Main Square at Siena, we will most certainly relish the Panforte, a delicious cake along with our meal.

A good dose of culture and a hearty meal complements the pleasure of cycling through the hills and vales surrounding the city with undulating paths and inhaling natural and clean air and this, helps us to complete a distance of approximately 30 miles intended for the fourth day.

After a mildly exhausting yet tremendously satisfying day cycling tour, we will depart, on the terrace or by the open fireplace and sip a glass of wine and enjoy the rest of the evening in this farmhouse, which is situated in a natural reserve packed with flora and fauna.

Did you know?
Siena has contributed to a lot to arts being the hometown of many artists. The list of artists from the Sienese School boasts of Duccio and his student Simone Martini, Martino di Bartolomeo and Pietro Lorenzetti. Innumerable priceless artworks of Renaissance and High Renaissance art remain even now in Siena's galleries or beautify churches in Siena. This includes Duccio's 'Madonna and Child with saints polyptych' painting found at the Pinacoteca Nazionale in Siena. Siena's twin town is Wetzlar, located in Germany.

Day 5 - Natural Hot Spas in Tuscany

Does Tuscany boast only about walled cities, Etruscan ruins, cultural heritage and delicious food? A modest little town, Bagna Vignoni, famed for its revitalizing spas and roman baths from time immemorial, has a few other sight-seeing places to visit and there is a fanciful restaurant at the site of the ancient baths.

After a day of rigorous cycling, it is heartwarming to dip one’s feet in one of the little streams that originate from the original ancient roman baths. We will take an unusual path and temporarily soak our slightly tired feet in the warm sulphur waters before venturing to explore the rest of the neighborhood.

Returning to your Villa you will spend a totally chilled evening reminiscing about the pleasant day.

Day 6 - Bicycling to Pienza, Origin of Renaissance in Tuscany

After relaxing the previous day, we will set out to explore Pienza, a UNESCO heritage town, built in renaissance style. Pope Pius II left his stamp on this tiny town where he was born by converting it into a present-day well-planned renaissance town.

Lunch is at a restaurant in the town. After we enjoy the world-famous Precorsin cheese we brace up to cycle through and explore the gorgeous Val D’Orcia, perhaps the stunning parts, and surely the most filmed parts of Tuscany. Cycling through the farmland lanes; some of which are old and gravelly, some are rough and natural, others that are concreted and well-laid may lead to the ultimate biking experience, exploring all surfaces and taking pleasure in the joys that each surface adds to biking.

Finally, we will go back to your villa to explore the environs around it that is as alluring as the rest of Tuscany.

Did you know?
Pienza is a classical example of Renaissance town design. Often seen depicted as the "utopian city", it stands for one of the well designed of Renaissance towns, where an example of perfect living and government was attempted, founded on the notion of a town competent to meet the needs of a coexisting and industrious population. Subsequently, it symbolized the so-called Utopia patronized by intellects and philosophers for centuries.

Day 7 - Cycling amidst the Towering Medieval Manhattan of Tuscany

Biking through the Tuscan landscape with us comprises exploring famous, popular trails, cycling through unusual paths in picturesque towns and valleys near Siena, including the walled town of San Gimignano, occasionally referred to as ‘Medieval Manhattan’ on account of its fourteen towers of varying height.
Exploring the vicinity and banking on the season, we possibly will see the beautiful crocus covering the fields with purple flowers and engulfing the entire town with its beauty. Many wildflowers also flourish in and around the town.
Lunch at a local trattoria, possibly some interaction with the locals, who are among the most friendly of all people, will refresh the mind, body and soul as we go ahead to see the other natural sights, including olive plantations and exclusive vineyards that produce the remarkable white wine, Vernaccia di San Gimignano.

As we return to your villa on the final day of our Tusany biking tour, you may just be tempted to sip the lovely white or sparkling red wines you may have bought along the way as bike tourists.

Did you know?
Situated in the heart of the city, the museum SanGimignano1300 presents a large-scale reconstruction of the town as it existed 700 years ago. Architects, antiquarians and a team of illustrators toiled almost three years to set up this magnificent and remarkable exhibition. This exhibition comprises 800 carefully handcrafted structures, 72 towers, street scenes, and figurines.

Recommended Reading

Tuscany Biking Overview from Travel-To-Tuscany.org

Enquire Now