We organise this unforgettable road bike experience with three days of relaxed cycling for those who don't want to spend a holiday entirely in the saddle and four nights in a selected charming hotels , besides every day, there are different options to make easier and shorter rides or more challenging ones , at your choice  . The hills of Tuscany, whether crowned by enchanting villages covered by vineyards and olive trees or immersed in the nature and full of wildflowers, have one thing in common: they are perfect for road bike rides with your friends !! 


Step into the unspoiled small towns, through wide valleys, along winding country roads, past cypress-lined paths and quiet woodlands. Ride a bike, explore the unforgettable Renaissance art and architecture, visit wineries and cellars: you will be in the heart of the Brunello wine region and taste gourmet cuisine made with fine local ingredients .


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.


4 Nights 3 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
  • Enjoy the Montepulciano Climb
  • Visit Montalcino and Montepulciano Vineyards 
  • Experience the Tuscan famous food and wine 
Pickup point
53026 Pienza, SI, Italia View on Map
Route Map
Route Map

Tours 4 Distance 180 km Elevation 3,230 m

Itinerary Route Map
Itinerary Route Map
Day 1 Day 2 Day 3 Day 4
Road Bike, Road E-Bike
3 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. The warm-up start soon going to San Quirico to test bikes and equipment , around 20 kilometers  ! You'll stop in the most attractive village of Horti Leonini Garden in town. 

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

Enjoy the ring  Montepulciano - Monticchiello. Start your day with a pleasant downhill, you will wind along a scenic path winding through vineyards, cypress trees and medieval villages... In the place you are going to traverse, you will encounter Castelmuzio And the hilltop village of Petroio. Today's journey will take you to Montepulciano, famous for producing Nobile di Monpulciano wine. Visit one of the typical wine cellars in town, the oldest wine cellar in town is located under Ricci Palace. Across Monticchiello back to Pienza

Day 3

Today's journey will take you to Bagno Vignoni, a spa town that dates back to Roman times before reaching the beautiful Castiglione d'Orcia. Enjoy the long downhill road to the monastery of Sant'Antimo, where you can receive one of the several church services performed daily by the monks. On the way to the Etruscan village and the wine town of Montalcino, you will set foot through magnificent vineyards. Montalcino is a fortified town that was used as a refuge by the nobles of Siena in the 16th century, but nowadays, thanks to Brunello di Montalcino, Italy’s premier wine production, the town is even more famous. Visit the fortress and admire the magnificent views of the entire valley where you just rode your bike, then reward yourself with dinner in our favourite wine cellar.

Day 4

From Montalcino to Siena  On the way,  you will cycle along the peaks of the forests, where the famous monastery of Monte Oliveto Maggiore is located. Stop here to visit the beautiful buildings and maybe have lunch in the restaurant. Afterwards, you will travel through the charming Le Crete region.  Easier: Start by descending 10 kilometers, passing Buonconvento. Head north towards Siena and you will ride a  gorgeous route along the secondary road. In the village of Murlo, you can visit the charming Etruscan Museum. Continue to admire the picturesque Ville di Corsano, and finally arrive at the Arch of Siena, Porta San Marco.

In the afternoon, you will have time to take a leisurely stroll in this medieval art city and visit Piazza del Campo , Torre del Mangia and the famous Duomo Cathedral. Piazza del Campo is famous because of the controversial "Palio" horse race held twice a year, which is the challenge of the 17 "trades" of this charming city



Self Guided Tours