Spend a week in Tuscany, cycling rolling hills, enjoy food, and wine: from the Val d'Orcia UNESCO protected site, via Crete Senesi and Chianti region, visiting some of the most enchanting towns like Pienza, Montalcino and Siena.
This itinerary will be a special combination of the classic Heart of Tuscany enriched by some spectacular rides, taste the typical tuscan dishes and world famous wines like Brunello di Montalcino and Chianti.
Day after day, pedaling among olive groves and vineyards, you’ll be immersed into the spirit of L'Eroica vintage cycling event, where people from all over the world come to Gaiole in Chianti to ride the gravel roads of Tuscany and seek out the authentic roots of this fantastic sport, with its great, popular heart, and rediscover the beauty of fatigue and the thrill of conquest.
HIGHLIGHTS
- Ride L'Eroica, the world's greatest vintage event
- Learn the secret of Tuscan lifestyle, taste local food and good wines
- Discover the UNESCO World Heritage Sites of Val d’Orcia and Siena
- Ride the Crete Senesi and Chianti wine region, the most beautiful rides in Tuscany
This itinerary will be a special combination of the classic Heart of Tuscany enriched by some spectacular rides, taste the typical tuscan dishes and world famous wines like Brunello di Montalcino and Chianti.
Day after day, pedaling among olive groves and vineyards, you’ll be immersed into the spirit of L'Eroica vintage cycling event, where people from all over the world come to Gaiole in Chianti to ride the gravel roads of Tuscany and seek out the authentic roots of this fantastic sport, with its great, popular heart, and rediscover the beauty of fatigue and the thrill of conquest.
HIGHLIGHTS
- Ride L'Eroica, the world's greatest vintage event
- Learn the secret of Tuscan lifestyle, taste local food and good wines
- Discover the UNESCO World Heritage Sites of Val d’Orcia and Siena
- Ride the Crete Senesi and Chianti wine region, the most beautiful rides in Tuscany
DURATION: 8 days/7 nights
PRICE PER PERSON IN DOUBLE: 3180,00 €
WHERE: Val d'Orcia - Crete Senesi - Chianti
WHEN: from 28 September to 5 October 2026
Itinerary
1
28 September - Benvenuti in Toscana
Individual arrival at Siena, meet our staff at 3 pm and private transfer to the first hotel located in San Quirico d'Orcia
Check-in into your room and welcome aperitif to introduce the Tuscany Bike Tour and L'Eroica week.
Dinner and accommodation in hotel.
2
29 September - Val d'Orcia region
56 km – Elevation gain: 910 meters
The landscapes of Val d'Orcia region, one of the most beautiful place in Tuscany and UNESCO world heritage site.
Visit of Pienza, the "ideal" city of the Renaissance time, also famous for its Pecorino cheese.
A quick stop at Montepulciano, with its winding streets and squares.
Monticchiello, a small medieval and charming town.
Bagno Vignoni, cute medieval town where the main square of the village is a big thermal pool which contains the original source of thermal water.
Take a relax break from the cycling journey and enjoy the SPA before dinner.
Dinner and accommodation in hotel.
3
30 September - Montalcino and Brunello region
54 km – Elevation gain: 1180 meters
Long climb direction Castiglione d’Orcia, the beautiful landscapes will compensate the challenging ascent. Stop in the town center and discover the Rocca di Tentennano
Up and down to reach the Brunello region and Sant’Antimo Abbey, the route will take you right in front this beautiful Abbey.
The Abbey of Sant’Antimo, one of the most beautiful romanic church in Tuscany.
Enjoy a Brunello wine tasting in one of the selected wineries along the route.
Stop to visit the town center of Montalcino, a perfect place for a tuscan lunch.
Back to San Quirico riding direction Torrenieri.
Dinner and accommodation in hotel.
4
1 October - Crete Senesi region and Siena
57 km – elevation gain: 890 meters
An unforgettable ride surrounded by the beautiful views of the Crete Senesi to the edge of Chianti wine region.
Crete Senesi, where Calanchi and biancane alternate in this suggestive territory.
Passage from San Giovanni d’Asso, the center of the white truffle of the Crete Senesi.
Discover Asciano, small villages with nice churches, streets and square. We suggest to eat something and refill the water bottles before the next part of the stage.
For the photography lovers, you’ll ride very slow this segment…The Via Lauretana offer unique landscapes and you’ll stop many times to take photos.
Siena at the horizon, the visit of this beautiful city will make unique your experience in Tuscany.
Dinner and accommodation at Villa Curina Resort.
5
2 October - Chianti Classico bike tour
Breakfast and one day guided bike tour to discover the Chianti region, one of the most important wine area in the world, for the quality of its wines and beauty of the landscapes. Chianti offers a unique landscapes: gentle hills covered by vineyards and olive groves, small stone villages and farm houses.
We'll start biking in the hearth of Chianti Classico, during the bike tour we will reach the Castle of Brolio, owned by the Ricasoli family since 1141, and the small villages of Villa a Sesta.
We will then stop in a local winery for a Chianti wine tour and tasting with lunch.
Dinner and accommodation in hotel.
6
3 October - Road to Gaiole in Chianti or Eroica
Bike tour to discover part of the Eroica route to Gaiole in Chianti, during the ride you can improve your confidence with the vintage bike, also on the gravel roads. We'll ride direction Pievasciata before to reach Gaiole in Chianti.
Lunch along the road and final arrival in Gaiole in Chianti, Visit of the Eroica festival and vintage market.
Alternative program for the participants to the Eroica longest route (135 km and 209 km). Early transfer to Gaiole in Chianti, participation to L'Eroica and transfer back to the hotel at the end of the race.
Dinner and accommodation.
7
4 October - L'Eroica
Early wake up early private transportation to Gaiole in Chianti to participate at the 2026 edition of L’Eroica - Shortest routes: 106 km, 81 km or 46 km.
At the end of the race pasta party and private transportation back to the hotel fot the final dinner.
8
5 October - Arrivederci Toscana
Breakfast and individual departures.
Airport or train station transfer available on request with extra charge.
WHAT'S INCLUDED
- 7 Nights stay with breakfast in double room
- 7 Dinners, drinks not included
- Light lunch, wine tasting and lunches included day by day
- Baggage transportation between the hotels
- Maps and information for your daily stage
- Van support each day with water and fruits
- Transfer from/to Gaiole in Chianti the day of L’Eroica
- Expert bike guide
- Guaranteed registration to L’Eroica 2026 (medical certificate mandatory)
- Eroica race package and souvenir
- Delivery of the race package in your room
- Private transfer from Siena to San Quirico d'Orcia on September 28
- Anima Toscana vintage bike jersey
NOT INCLUDED
- Tourist city tax
- Drinks
- Medical insurance
OPTIONAL SERVICES (PRICES ON REQUEST)
- Medical insurance
- Eroica registration discount for non-cyclist
- Medical/baggage insurance
- Bike rental
- Activities for non-cyclist (cooking class, truffle hunting, guided tours, horse back riding, trekking and more)
- Private transfer: airport, train station or other hotels
PRICE PER PERSON IN DOUBLE ROOM
3180,00 €
*Tour and prices guaranteed with a minimum of participants.
*Tour and prices guaranteed with a minimum of participants.
LODGING
Hotel Casanova
Look at the web site
.jpg)
Villa Curina Resort
Immersed in the peace of the countryside, surrounded by the rolling hills of Chianti and just a few kilometres from Siena, stands Villa Curina Resort, a small 16th century village rich in history and charm where you can enjoy a charming and refined holiday.
Visit the web site
Villa Curina Resort
Immersed in the peace of the countryside, surrounded by the rolling hills of Chianti and just a few kilometres from Siena, stands Villa Curina Resort, a small 16th century village rich in history and charm where you can enjoy a charming and refined holiday.
Visit the web site
Share:
€3,180.00
Price per person
