We propose this wonderful road bike experience with six days of intermediate cycling for those who don't want to spend the time entirely on the bike and six nights in a selected charming hotels , besides every day, there are different options to make more challenging rides , at your choice.....

Our wonderful bike experience will take part from Reinassance town Pienza to arrive magnificent San Gimignano . You'll cross the heart of Tuscany :  the lush Val d’Orcia , small towns of Pienza, Montalcino , Monticchiello,Gaiole in Chianti and more.. , the medieval castello di Gargonza where you will be guest,  you'll pass several vineyards, and afterwards you'll arrive to the beautiful San Gimignano and Etruscan town Volterra.

All together in this self guided for experienced bikers – anyway the average is 60/70 km and allow time to visit all the sights along the way..


After all relax yourself in the charming Tuscan resorts......


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


This is a Self Guided Tour where you'll have the freedom to choose your time without a local expert cyclist !


Group Bookings

Groups of 6 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 6 Days 21 Oct, 22 Oct, and 23 Oct Pienza, Toscana
What we'll give. What we won't

What is included in the tour

  • Accommodation in double rooms in a charming Tuscan resorts on double occupancy 
  • Full Cyclist Breakfast
  • High Quality Cycle ( Gravel , Carbon or E-Bike )
  • Car Support on request in case of problems ( a car will pick you and bring you at home )
  • 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
  • Take in stunning views of Tuscany Hills and Val D'Orcia
  • Reach the wonderful hills between Pienza and Montalcino
  • Visit Montalcino and Chianti Vineyards 
  • Experience the Tuscan famous food and wine 
  • Breathe the history: Magical stay in Gargonza medieval castle, XV century convent in Pienza, renaissance palace in San Gimignano.
  • The oldest town in Tuscany Volterra founded before Roman times 
  • Pecorino cheese, Brunello wine & bruschetta 
  • Homemade Gelato Tour
Pickup point
53026 Pienza, SI, Italia View on Map
Route Map
Route Map

Tours 4 Distance 180 km Elevation 6,160 m

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

Day 1

Pienza is the "perfect town", an outstanding representative of Renaissance town planning. You'll find beautiful buildings and narrow street where strolling on the cobblestone is a treat. Gift hunters will also be fascinated by the handmade shops. Pienza is also a veritable gourmet paradise. Meet and greet, we will set up your bicycle and introduce you to daily riding.

Ring ride across Montepulciano and Monticchiello , around 35 km. 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".

Your charming Hotel is housed in a 15th-century convent in a quiet, secluded location right in the centre of Pienza. Entirely rebuilt between 1459 and 1462, itself is a rare masterpiece : it was the brainstorm of Pope Pius II

Day 2

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 available longer ride via San Filippo and Abbadia  for a total ride of100km

Day 3

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 - Available extension via Asciano

Day 4

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. . 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 Total Distance 64 km/40 miles - Available extension to Monte Luco

Day 5

Going to San Gimignano: more vineyards will await for us now, but you'll be surprised at how different they seem once we get into the area of San Gimignano. Soon you pass Monteriggioni, literally a town-in-a-castle. Barely two hundred yards across, its eighty residents all reside within the picture-perfect . Soft and colourful hills, beautiful vineyards and lush sunflowers provide the backdrop to Etruscan ruines on your route to San Gimignano’s "medieval skyscrapers” and in the distance you will see the town's seventeen towers. 
You'll have plenty of time to wander through the cobble stoned streets, and buy a few last-minute Tuscan mementos for you and your friends 
Total Distance: 60 km/37 miles

Day 6

On the last day  you will leave San Gimignano and will cycle to the ancient Etruscan town of Volterra. Through a patchwork-like landscape dotted with wheat fields, olive groves and hills, you reach the base of the imposing hill upon which the town is set. Before arriving to the old town you'll face a challenging climb . The “magic and mysterious” city of Volterra has its roots in three thousand years of history. It's possible to find evidences and signs by every historical period which gives the artistic city a unique aspect.
Total Distance 60 km / 37 miles


Self-Guided Tours