Permanent route of L'Eroica in 4 stages - Self Guided

Permanent route of L'Eroica in 4 stages - Self Guided


  6 days/5 nights


660,00 €


  Active rider

The Permanent Route of L'Eroica is a unique experience where you can live the adventure of L'Eroica all year round. The permanent route is long 209 km in the heart of the Terre di Siena region, through Chianti, Crete Senesi and Val d'Orcia. It’s a journey into the essence of the legendary Tuscan landscape, characterized by challenging and technical segments that make this route a great opportunity to practice cycling. The route alternates paved and gravel roads and has a total elevation gain around 3800 meters. Gravel roads cover approximately 112 km on 209 km. The route will be divided in 4 stages long between 45 and 60 km with more than 800 meters of elevation gain each day.
The package can be organized starting from Radda in Chianti or Gaiole in Chianti.  
DURATION: 6 days/5 nights
PRICE FROM: 660,00 €
WHERE: Chianti - Siena - Montalcino - Val d'Orcia - Crete Senesi
WHEN: all year long



Day 1 - Benvenuti in Toscana

Individual arrival in Siena, dinner on your own and accommodation in 3 stars hotel. Hotel 4 stars available on request with extra charge.

Meet and greet with our staff, delivery of the maps and briefing where we'll explain the bike tour.


Day 2 - From Siena to Montalcino

56 km – elevation gain: 1150 meters

Just leaving the city of Siena you’ll ride through a very typical segment of the route, located between “Colle Malamerenda” and Radi, deep in the gentle hills of Siena, studded of farmhouses, medieval villages, merging your ride with the Via Francigena itinerary. The village of Murlo will be the landscape of the easiest segment of the whole permanent route.
Climbing Castiglion del Bosco, one of the most engaging segments of L’Eroica permanent route, you will reach Montalcino over the beautiful and panoramic lands of the Brunello of Montalcino. Montalcino, also famous for olive oil and honey, it’s a nice village that merits a visit, even to admire the incredible panorama opening on the Val d’Orcia area.

Dinner on your own and accommodation in 3 stars hotel located in the town center of Montalcino.


Day 3 - Val d'Orcia and Crete Senesi

63 km – elevation gain: 1030 meters

The descent from Montalcino will be a dive surrounded by the Brunello vineyards and will take you to the Val d’Orcia and Lucignano d'Asso, where you can take a rest with a typical snack or just to refill your water bottle. The gravel road between Torrenieri and Lucignano d’Asso it’s one of the most fascinating and characteristic of the Eroica route. Pedaling surrounded by the landscape of Val d'Orcia region is a privilege for the eyes and mind that restores the fatigue caused by the up and downs roads.
From the vineyards and rolling hills to the suggestion of the lunar landscape is a short step. Left the villages along the Cassia you’ll immerse in the Crete Senesi region, with the characteristic gullies. The oak and cypress indicate isolated farms where they produce cheese and tables are enriched by the diamond of Crete Senesi: the white truffle.
An alternative route will take you to visit the Abbey of Monte Oliveto and the small village of Chiusure, before to reach Asciano.

Dinner on your own and accommodation in agriturismo.


Day 4 - Monte Sante Marie and Chianti

53 km – elevation gain: 1230 meters

The first part of the stage includes the challenging gravel road of Monte Sante Marie, very famous sector of the Strade Bianche pro race that will take you back in the Chianti area.
You will reach the Chianti wine region through Castelnuovo Berardenga, the village on the border with the Crete Senesi.
A kind of summary of what you saw and what you will see is the road to Pianella that presents different landscapes. The road to Radda in Chianti will be a sequence of vineyards and woods, passing through pretty villages and farms, that could offer you a wide range of typical products, wine and olive oil tasting, temptations that will delight your itinerary and your senses. You’ll finally arrive Radda in Chianti that merits a visit to its historical village.

Dinner on your own and accommodation in 4 stars hotel.


Day 5 - Gaiole in Chianti and Castello di Brolio

47 km – elevation gain: 800 meters

After Radda in Chianti you’ll be headed to Gaiole, town where L’Eroica was born on 1997, going down through Vertine, a nice little pearl of the Chianti.
The official Eroica route starts in Gaiole in Chianti, winding among historical vineyards that lead you to Castello di Brolio, with its cypress-lined entrance. The breath-taking panorama below the walls, over the vineyards, represents one of the most wonderful parts of the cycling holiday. You can decide also to visit the Castle, owned by the Ricasoli family since 1141, or taste a glass of Chianti Classico at the enoteca.
After a few kilometers, near San Giovanni a Cerreto, Siena will appear on the horizon. The visit to this wonderful medieval city with its Dome, Piazza del Campo and the perfect medieval city center will make your trip special. The ordinates cultivation of vines is fading into a more various landscape, painted with terra di Siena color.

Dinner on your own and accommodation in 3 stars hotel. Hotel 4 stars available on request with extra charge.


Day 6 - Aarrivederci Toscana!

Breakfast and individual departure.

  • 5 Nights stay with breakfast in double room
  • Baggage transportation between the hotels
  • Informations for your daily stage
  • Maps with altimetry of each stage in PDF file
  • GPX tracks for GPS or mobile App.
  • Phone assistance by Anima Toscana staff
  • Tourist city tax
  • Medical insurance
  • Medical insurance
  • Upgrade in 4 stars hotels
  • Discount baggage transportations
  • Activities for non-cyclist (cooking classes, wine tours, trekking)
  • Bike rental (Road, hybrid, MTB, Gravel, vintage bikes or electric bikes)
  • Bike guide in english, french, spanish or german language during each stage
  • Van support during your daily stage, to let you enjoy your Tuscan vacation
  • Extra intervention of technical assistance
  • GPS rental
  • Guided tours of cities and villages
From 660,00 €