Join us and plunge into Tuscany: this bike experience will bring straight to the rolling hills and to the fortified medieval villages of unspoiled Tuscany. The goal of the road bike tour, is not only cycling , but even to enjoy the real Tuscan cuisine: fruity olive oil, pecorino goat cheese and the classic best Tuscan wine: Brunello di Montalcino, Chianti Classico and Vino Nobile di Montepulciano  . In our special event, you will taste some of our favourite producers. Travelling with a small group of adventurers and Tuscany's local expert cycling guide, you will enjoy the perfect combination of nature, culture, cuisine and fun.


Choose between  Road Bike , E-Road Bike and Gravel Bike , as you prefer !


This is a Guided Tour where you'll have the support of a local expert cyclist !


Group Bookings

Groups of 4 or more riders: can opt to make a tour private and choose their own dates.
Groups of 8 or more riders: can benefit from a 5% discount.


6 Nights 5 Days Available on request Pienza, Toscana
What we'll give. What we won't

What is included in the tour

  • Accommodation in double rooms in a Superior Tuscan resorts on double occupancy 
  • Dinner providing all the evening meals along with beer and soft drinks either at the house or hotel or out at carefully selected restaurants . Our tours aren’t just about great cycling they’re also about great food.
  • Full Cyclist Breakfast
  • Cost for 1 or 2 guides (for the group of maximum 16 cyclists so 1 guide for 8 group members)
  • First mechanical aid kit (our cyclist and support vehicle are certified in handling first mechanical aid situations)
  • Car Support with Cycle porter ( if you wish to stop your ride , a car will pick you and bring you at home )
  • The support vehicle will always make itself available to provide you with complimentary refreshments , bars, gels, sports powder + bottled water, and preferred salty/sugary snacks for feed stations.
  • High Quality Cycle ( Gravel , Road Bike or Road E-Bike )
  • Car Support 
  • Sightseeing and shopping suggestions
  • All Baggage transfers
  • Pick-up of bikes and gear in Castellina
  • Taxes and VAT

What is NOT included in the tour

  • Any meals/services not mentioned in the inclusions
  • Mandatory Travel Insurance for Cyclists and Travel Insurance Bike / EUR 50 per person
  • Any charges for video cameras, still cameras, etc.
  • Wine, alcoholic beverages , long drinks, etc.
  • Personal expenses like tips, telephone calls, laundry, etc.
  • Any costs arising out of unforeseen circumstances like landslides, road blocks, bad weather, etc.
What makes this tour special
  • Full immersion in Val d’Orcia
  • Stay in Pienza the famous renaissance city
  • Magical stay at an original medieval castle Gargonza
  • Riding through scenic landscapes where “English Patient” and “Gladiator” has been filmed
  • A private tour of the Cellar of Brunello in Montalcino, the Biodinamic Corte Pavone
  • Enjoy Chianti resort with wine & food focus, Michelin star
Pickup point
53026 Pienza, SI, Italia View on Map
Route Map
Route Map

Tours 6 Distance 322 km Elevation 5,940 m

Itinerary Route Map
Itinerary Route Map
Day 1 Day 2 Day 3 Day 4 Day 5 Day 6
Relax, Intermediate
Road Bike, Road E-Bike, Gravel Bike
5 Days

Day 1

Meet at Chiusi-Chianciano train station at 12:00 pm (stop on all major routes from Florence to Rome). Transfer to Pienza, the most complete Renaissance in the world. You'll be accommodated in a superior hotel double room, the hotel is located in a 15th century monastery in the city center. Meet your guide and get acquainted with others while there will be the bike fitting at 3 pm. Optional (depending on weather conditions and time of use of bicycle accessories) short drive to Bagno Vignoni: This ancient village is located in the heart of Tuscany, in the Val d'Orcia Natural Park.

Thanks to Via Francigena (which was the main route used by ancient pilgrims to Rome), these thermal waters were discovered and used since Roman times. The center of the village is the "Water Source Plaza", a rectangular water tank that originated in the 16th century, which contains the original water source from the underground aquifer of the volcanic source. Enjoy a welcome dinner in the wonderful La Bandita townhouse in Pienza, where you will taste special homemade pasta.

Day 2

Ring ride across Montepulciano and Monticchiello. Starting the day with a pleasant downhill, you will wind along a scenic path that winds through vineyards, cypress trees and medieval villages. This is the filming location of "English Patient". The sights you will travel through include the hilltop villages of Castelmuzio and Petroio.

Today's journey will take you to Montepulciano, famous for producing Nobile di Montepulciano wine. After strolling through the medieval streets of this village, you can stop to visit one of the typical wine cellars in town, the oldest wine cellar is located under the Royal Palace . Return to Pienza through another hilltop village, Monticchiello! Total distance 55 km / 34 miles


Day 3

Loop ride to Montalcino
Today we'll begin on a spectacular descent into the soft green hills of the Val d'Orcia: You are now at Parco Naturale e Artistico della Val d’Orcia, an Unesco site with this main reason: “ The Val d’Orcia is an exceptional reflection of the way the landscape was written in Renaissance period to reflect the ideals of good governance and to create an aesthetically pleasing pictures.” Imagine cycling up and down in a scene from painting... Along the way face the hearty uphill to Castiglione d'Orcia, with the imposing Rocca A Tentennano. After a rest, enjoy a long downhill to Sant'Antimo Abbey , your next stop: if you have luck, you will hear the monks chanting. On your way to the Etruscan village and wine town of Montalcino you’ll pedal through magnificent vineyards. It is a fortified town which was used as a shelter by Siena nobles during the 16th Century. Today it is even more famous thanks to the production of one of Italy's premier fine red wines, Brunello di Montalcino.
Let’s go to Corte Pavone an organic-biodynamic winery for wine tasting.
Back to Pienza via San Quirico d’Orcia: stop in the village at Horti Leonini Garden, the top attraction of town. Free dinner in town
Total Distance: 68 km/42,5 miles

Day 4

Le Crete, Castelmuzio, Trequanda, Lucignano
Your detailed directions will take you through typical postcard scenery of Tuscany, Italy’s most photographed region—for good reasons. Following a picturesque road, you’ll ride by Castelmuzio, Trequanda. Afterwards, you'll travel through the fascinating area called Le Crete, Tuscany's answer to the Badlands, with strange rock formations and lone farmhouses flanked by twin cypress trees. Here the verdant hills give way to little domes of clay and Tuscany reveals another face of its identity, an unusual, almost lunar landscape of chalk cliffs and gullies soaked in a primeval atmosphere. Cycle in the valley for a while and reach Lucignano, a small village that represents one of the more extraordinary examples of medieval urban planning for its system of elliptic rings arrived intact over the centuries.
Destination is a real castle restored – its magical!
Dinner at your Castello di Gargonza
Total Distance: 57 km/35 miles

Day 5

Castelnuovo Berardenga, Castello di Brolio,
Pedaling north, we'll whisk past a pair of typical southern Tuscany towns and make a 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 passing through many little hamlet. Not-to-be-missed is Castello di Brolio, a castle and winery, home of Barone Ricasoli and his world-renowned wine – where you will enjoy an amazing wine tour.
After nice gentle downhill wait for you to reach Gaiole in Chianti, a lively town located along the river Massellone and home to the annual l'Eroica vintage (pre-1987 steel frame) bicycle race the up and down and get to your Castle-hotel on the border of this hill town.
Dinner in town
Total Distance 55 km / 34 miles

Day 6

Ring ride to heart of Chianti: 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.. A few more miles bring us to Radda in Chianti and the way back on the so called via dei Castelli not to be missed the stop at castello di Ama to visit the winery and the borgo. Relax by the vanishing edge pool spilling into the countryside of endless vineyards
Farewell dinner at il Pievano Michelin star restaurant
Total Distance: 62 km/39 miles

Guided Tours