Cycling Tuscan Wine Country


Yes, there are hills to climb, but your efforts will be well rewarded with a sunny Mediterranean ambiance and a spirited flair for hospitality, Tuscany nourishes the soul and leads you to rejoice in the earthly pleasures of daily life.
Route we selected takes you along tranquil country lanes tracing the expanses between farmland crowned with walled villages, ancient monasteries in secluded valleys, and medieval forts. Staying in Pienza, Montalcino, Siena and heart of Chianti, you are sure to experience the true essence of Tuscany, where history and beauty fill the heart as water fills a well.
Strongly suggested, after spinning through rolling vineyards, golden wheat fields and chalky white hills by day, savor pecorino cheese, homemade pasta pici, fruity olive oils and sip Tuscan wines Brunello and Nobile.


  • Journey into the heart of Chianti—and back in time—to sensational Siena and Castelllina
  • Shadow the hilly course of L’Eroica, Tuscany’s internationally recognized vintage bike race
  • In ancient cellars, taste superb Tuscan wines, from Vino Nobile di Montepulciano to Brunello di Montalcino

Day by Day

DAY 1 Pienza “The Perfect Town”
Meet you at your hotel in Pienza, the purest renaissance town in the world, for welcome and bike fitting. Pienza the “perfect town” is a remarkable example of Renaissance-era town planning. If you have even the least appreciation for beautiful architecture, it is a treat to stroll around its cobblestone streets. Gift hunters will also be enthralled. Pienza is also a veritable gastronomic paradise. Optional test ride to San Quirico d’Orcia 20km /12,5 mi

DAY 2 Montepulciano & Vino Nobile. Distance 55km/ 34 mi
Cycling: Loop to Castelmuzio, Montichiello and Montepulciano the jewel of Southern Tuscany. Be sure to stop along the way to visit the remote convent where parts of The English Patient were filmed, and in the enchanting little hamlet of Castelmuzio. By lunchtime you’ll come to Montepulciano, full of Renaissance palaces. After relaxing a while, return to Pienza with a stop in the village of Monticchiello, the quintessential Tuscan hill town.

DAY 3 Montalcino Brunello Land. Distance 46 km/ 28,5 mi
Cycling: Ride from Pienza to Montalcino, with a pause in fairy-tale Bagno Vignoni, a miniature spa that is among the most unique towns in Europe. You can have lunch in Castiglione d’Orcia, then push on to the monastery of Sant’Antimo, where you might catch one of several vesper services performed by the monks. The famed wine town of Montalcino is your destination. Visit the fortress to see a breathtaking view of the entire valley you’ve just biked.

DAY 4 Siena & Monte Oliveto Maggiore Abbey. Distance 58 km/ 36 mi
Cycling: Start long downhill followed by gentle uphill to Monte Oliveto Maggiore, a Benedictine abbey built in the 13th century and famous for its frescoed cloister and stunning setting. Follow the fascinating area called Le Crete, Tuscany’s answer to the Badlands. Here the verdant hills give way to little domes of clay and Tuscany reveals another face of its identity.

DAY 5 Chianti Hills. Distance 50 km/31 mi
Cycling: reach Castellina in Chianti following the “Chiantigiana” road.Along the way you can stop at Castelnuovo Berardenga, a medieval town that marks the gateway to Chianti country. From here you will ride inside the vineyard of famous chianti classico wine. Not-to-be-missed is Castello di Brolio, a castle and winery. Arrive in time in Radda for a light lunch and enjoy the last 10 km of gentle rolling hills to get in Castellina .

DAY 6 Greve in Chianti & Panzano. Distance 52km/ 32,5 mi
Cycling: Loop to Panzano. Bike along quiet roads to the three villages that formed the Chianti Alliance centuries ago. Visit Tuscany’s forgotten abbeys and hamlets then enjoy a winery tour and taste their supple reds, fresh honeys and rich olive oil . Have a stop at Greve’s main piazza, characterized by an original formation of irregular triangular shape. Back via Panzano with preserved old walls, gate and the keep of the medieval castle.

DAY 7 Monteriggioni. Distance 30km/18,5 mi
Cycling: loop to Monteriggioni, literally a town-in-a castle.Barely two hundred yards across, its eighty residents all reside within the picture-perfect round turreted walls that crown the hilltop visible for miles around. . End of Tour

All tours offered are customizable


Cost: Euro 1290 p/person

Tour Name: Cycling Tuscan Wine Country
Tour Type: Self Guided Cycling Tour
Price based on double accommodations. Single supplement euro 350


  • Six nights in excellent four & three-star superior hotels
  • Six breakfasts
  • Route notes, maps, elevation gain and city map
  • Sightseeing, restaurant and shopping suggestions
  • All Baggage transfers
  • Pick-up of bikes and gear in Castellina
  • Keepsake Cicloposse water bottle
  • Sales taxes

Not included:

  • Bike Rental: Hybrid/Touring bike euro 140. Race bike euro 180 -all equipment is included. E-bike available on request.
  • City tax: each village charge a tax per each day between euro 0,70 to 2,50 this can be paid only in cash to hotel for local administration

Daily Mileage: 30-35 miles on gently rolling terrain with some climbs. Additional mileage available on request.
Tour Departures: Any date between 15th March to end of October
Length: The base tour is 6 nights but is possible take the first part (4 nights) or add some days.




Day 1 & 2 Relais Il Chiostro di Pienza

Il Chiostro di Pienza is housed in a 15th C convent and sits protected and quiet right in the center of this tiny town. It has been renovated but all the beamed ceilings frescoed walls and ancient tile floors have been preserved, nice garden overlooking val d’Orcia with pool. View hotel website>>

Day 3 Si Montalcino

Hotel SI Montalcino is small charming hotel completely renovated, located on the panoramic road to S.Angelo in Colle, one km away from the walls of Montalcino. It is on a natural terrace that dominates the valley overlooking Monte Amiata and from here you can admire the vineyards of Brunello. Pool Belvedere View hotel website>>

Day 4 Hotel Palazzo Ravizza, Siena

Palazzo Ravizza is a renaissance Palace, which stands in a quiet area of the historical center of Siena. It was transformed into hotel in the 1920′s and it has been recently renovated to offer modern facilities while maintaining original character. Lovely rooms and beautiful garden overlooking the Tuscan hills.  View hotel website>>


Day 5 & 6 Hotel Palazzo Squarcialupi, Castellina in Chianti

Palazzo Squarcialupi is part of the history of Castellina in Chianti. It is situated in the historical town center, on a road running along the XV century City Wall. It has medieval origins and it has been renewed becoming a luxury Palace.  View hotel website>>


Upgrade in Pienza: La Bandita Townhouse

La Bandita Townhouse is a luxury boutique hotel tucked inside the historic center of Pienza. The building is a rambling Renaissance-era palazzo where nuns have lived for over 500 years. the property itself blends in completely with the Renaissance character, is a comfortable, and stylish place.  View hotel website>>


Upgrade in Castellina in Chianti: Hotel Salivolpi

Salivolpi is an old country house recently converted into a hotel whilst keeping its original architectural features. It is located on the hills on the site of the former Etruscan Castellina, surrounded by vineyards, olive groves and cypress trees, it has a wonderful panorama stretching over the Elsa valley.  View hotel website>>

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