Nicola & Aurélia
are at your service!
+44 20 3239 4967

Ride the Eroica among world famous vineyards

7 days / 6 nights
Tuscany - Leisure cycling - Self-guided road cycling - E-bike tours - Self-guided - E-bike - Self-guided
Without guide - Families - Luggage transfer

Last updated: 25/11/2023

price from 1120 € per pers.

Follow the route of the world renowned vintage bike race, the Eroica, passing through Tuscan hilltop towns, villages, vineyards and olive groves. A classic ride in classic Italian countryside, in the Tuscan region of Chianti. Follow the route of this legendary race, experiencing the "Strade Bianche" (unpaved white roads) that take you through the heart of this magnificent countryside. This is a must for all fans of cycling and all lovers of Italian countryside, food and wine. A perfect combination!

Prepare your trip

Your day by day program


Arrive in the superb city of Sienna and get settled into your hotel. This is an excellent opportunity to discover one of the most beautiful towns in the whole of Tuscany.

Sienna to Buonconvento

This is a wonderful first day's ride, immediately launching you into the typically beautiful rolling countryside of the Chianti region of Tuscany. After a relatively easy ride, you will arrive in one of the most reputed wine growing areas in the whole of Tuscany.
Night in a wonderful agriturismo with swimming pool. Excellent food made from local products and their own olice oil.
Distance: Approximately 40km.

Montalcino and the local "Brunello"

Today you are free to ride a loop which will take you to Montalcino, the point at which the Eroica culminates with an altitude of 600m. It is a pretty hill top town, with a fortress.
It is a difficult but rewarding stage. Rewarded perhaps by trying the "Brunello di Montalcino" one of Italy's most famous wines.
You will return back to the same agriturismo, to enjoy the pool and the delicious food.
Approximately 60km.

Buonconvento to Castelnuovo

This day will lead you to the village of Asciano through completely different landscapes from those previously encountered via the famous "Strade Bianche". During this ride you will discover some monuments such as the Santa Maria Abbey of Monte Oliveto Maggiore or the church of Saint Agathe. The ride is a series of small climbs and descents with some steep gradients.
You will continue your way to the village of Castelnuovo Berardenga. Your stop for the night will be in a small village nestled in the heart of the vineyards.
Environ 46 km.

Castelnuovo to Radda in Chianti

Today you will head north in the direction of Radda in Chianti, perched at more than 500m in altitude. You will need to accomplish several climbs in order to reach today's goal. But you will certainly not regret it once you have arrived, as Radda in Chianti has to be one of the most magnificent fortified villages which has been inhabited since the 9th century. This is picture postcard countryside rich in vineyards and olive groves.
Distance: approximately 35km.

Radda in Chianti to Sienna

This last day's riding is superb, alternating between tiny roads and the "strade bianche". The terrain is easier to ride than on the other days but the scenery still remains magnificent.
Once more you can enjoy all of the riches that Sienna has to offer you
Distance: Approximately 40km.

End of your holiday

Your holiday ends after breakfast in Sienna. Contact us should you wish to extend your itinerary.

Departure board

Starts any day from April to October.

Technical information

Fact sheet
Starting point
  • Start at your first hotel in Sienna
  • On day 7, after your breakfast in Sienna
  • Nights in agriturismos or comfortable hotels along the Eroica route. Some of the accommodations have a swimming pool.
Number of people
  • From two persons
Level of difficulty
  • A discovery route, open to all including leisurely cyclists. Distances between 35 and 60km.
  • Your luggage will be transferred daily so that you only need to ride with the bare minimum (camera, water, etc)
  • Bike hire (leisure bike or mountain bike) including delivery and rapatriation : 180€
  • Bike hire (electric bike or road bike) including delivery and rapatriation : 250€
  • Single room : 235€
  • July/August supplement : 30€
  • GPS tracks on USB stick : 25€
  • All nights in agriturismos or hotels (double rooms), all breakfasts, route notes and maps, luggage transfers between each stage.
Not included
  • Transport options before the trip commences and after the trip finishes, transfers not provided or foreseen in the programme, insurance, drinks or meals, the bicycles and any repairs needed, travel insurance, optional site visits, personal expenses.


Clients feedback

Felix L. 25 September 2018

Had an amazing time on our short, self-guided bike trip through Tuscany. The area is beautiful, especially the stretch from the outskirts of Florence to Radda in Chianti. Lots of wineries with consistently good wine. Everything was well coordinated in terms of bike delivery, luggage transport, and hotel booking. Had some initial difficulty with the bikes and with navigation but everything went smoothly afterwards.

Similar holidays

vélo toscane

From the Apuan Alps to San Gimignano via Florence

Tuscany - Self-guided road cycling - Culture & gastronomy - Self-guided - 8 days / 7 nights

price from 799 € View

The most beautiful Tuscan routes from Pisa to Florence in 6 days

Tuscany - Leisure cycling - E-bike tours - Self-guided - E-bike - 6 days / 5 nights

price from 825 € View
vélo toscane

Our Giro di Toscana original version with assistance

Tuscany - Elba - Guided road cycling - Private groups - Join a group - 8 days / 7 nights

price from 1490 € View
By continuing your visit to this site, you accept the use of cookies to offer you services and offers tailored to your interests.CLOSE  x
Subscribe to our
monthly newsletter