The Wonderful South Tuscany Tour will bring you across some of the most unbelievable views in the Italy , with picturesque scenarios full of surprises, where you can see hidden Italy gems.

In the region that has made hospitality an art, you will enjoy a combination of charming accommodation and delightful restaurants, handpicked and personally selected by us.

The goal of this cycling experience isn't just to ensure that you challenge hard climbs or do several kilometres  but also to make sure that you enjoy the best of Tuscany.

The Wonderful South Tuscany Tour will lead you through Tuscany and Lazio in 6 days. The tour is suitable for an intermediate level, always escorted by our local expert cyclist guide cycling alongside the group as well as our minibus providing support if required.



This is an intermediate tour and requires a good level of training !


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 Siena, Toscana
What we'll give. What we won't

What is included in the tour

  • Accommodation in double rooms in a charming  farmhouses or superior bike hotel on double occupancy  . 
  • Full Cyclist Breakfast
  • 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.
  • High Quality Cycle ( Alloy , Carbon or E-Bike )
  • Expert Local Cyclist will drive you during all your cycling experience
  • First Aid / Medical kit
  • 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 )
  • Luggage Transfer
  • Arrival/departure transfers from Florence/Pisa Airports   . We will pick you up and drop you off at the required airport. If it’s a shared tour we will ask all the clients to arrive around a certain time to enable us to collect everyone and avoid people waiting for too long at airports. 
  • 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 Chianti hills
  • Reach the wonderful towns like Siena , Montalcino and Bolsena
  • Enjoy the hard Montalcino Climbs
  • Discover the Etruria wild and lush nature 
  • Experience the Tuscan famous food and wine 
Pickup point
53100 Siena, SI, Italia View on Map
Route Map
Route Map

Tours 5 Distance 383 km Elevation 6,070 m

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

Day 1 

Arrival in Siena, welcome from the staff.
Presentation of the bike tour, preparation of bikes, welcome drink and then dinner Monteriggioni Castle.
Overnight at Sangallo Park Hotel

Day 2

Our first contact with this extraordinary region takes place in the Chianti Hills area.
This area, famous all over the world, gives the name to the excellent Chianti wine.
We’ll start our cycling day directly from our Hotel in Siena and heading to Gaiole in Chianti, we’ll ride through these rolling hills, surrounded by vineyards deep in an enchanting landscape.
Once we arrive in Radda in Chianti we’ll stop for a cappuccino and cornetto in its  magnificent old square.
After our stop, we’ll keep on riding up and down, enjoying breathtaking views: vineyards and wild areas. going through historic villages.
Getting to the Hotel, we can wind down in his swimming pool and get ready for our delicious dinner in Siena.
Overnight at Sangallo Park Hotel

Day 3

After an excellent breakfast, departure towards Monteroni D’Arbia on quieter secondary roads, through the magnificent Val d’Arbia. We will then continue towards Asciano, with its splendid Monte Oliveto Maggiore abbey. Riding up and down between hills and cypress trees you will arrive at Buonconvento, in the Ombrone valley. The final stretch of the day’s ride takes us to our destination today: Montalcino. This town is well-known for the production of the famous Brunello wine, which you may be interested to know is never sold less than five years after the grape harvest, and becomes “Reserve” after at least six years . Welcoming accommodation and an excellent dinner of local food and fine wine bring this first day by bike to an end.
Overnight at Hotel dei Capitani

Day 4

A new unforgettable day is waiting for us.
Today we’ll get in touch with the unique Val D’Orcia,riding on peaceful back roads.
We’ll start our day dealing with the descent from Montalcino to Torrenieri, then we ride with continuous up and down through ancient villages, where we’ll have our inevitable cappuccino and espresso.
Then, we must absolutely visit the splendid San Quirico d’Orcia, where we can have a lunch in a typical “trattoria” to recovery energy for taking on the demanding Montalcino ascent.
This ascent is 10 km long with a difference in altitude of 500m.
An exclusive dinner in this fairy-tale village will close our fourth day.
Overnight at Hotel dei Capitani

Day 5

Another superb day through villages surrounded by breathtaking nature.
San Quirico d’Orcia is the first village we encounter, the spa in its hamlet Bagno Vignoni is famous. Radicofani, a wonderful village dominated by a castle, is waiting for us along the way. Finally, we ride into the Lazio region at Acquapendente, where we will be justly rewarded for our efforts with a visit of the historical centre and an excellent dinner.
Overnight at Sant Apollinare Farmhouse

Day 6

A change of scenery is the main feature of today’s ride: we ride back, briefly, into the Tuscany region and arrive in Pitigliano, with its characteristic historical center called “Little Jerusalem” because of the presence of an ancient Jewish community. After leaving Pitigliano we head for Lake Bolsena, a destination that coincides with our return to the Lazio region, Civita di Bagnoregio is waiting for us. Here, a very different landscape will provide the ideal setting for an evening in good company and a delicious dinner.
Overnight at Hotel Royal

Day 7

Breakfast and transfer by minibus back to Siena.





Guided Tours