Tuscany Bike Tour and L'Eroica Gaiole

Duration

8 days/7 nights

Price

2580,00 €

Level

Active rider

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

DURATION: 8 days/7 nights

PRICE PER PERSON IN DOUBLE: 2580,00 €

WHERE: Val d'Orcia - Crete Senesi - Chianti - Siena

WHEN: from 29 September to 6 October 2025

Itinerary

26 September - Benvenuti in Toscana

Individual arrival at Siena, meet our staff 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.

30 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.

1 October - 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.

2 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 in local restaurant and accommodation in hotel located outside the city center of Siena.

3 October - Chianti Classico and Monteriggioni

53 km – Elevation gain: 750 meters

Daily ride to discover the Chianti area and Monteriggioni.
Long climb direction Castellina in Chianti, passing Fonterutoli and surrounded by beautiful views over the Val d’Elsa.
Castellina in Chianti, interesting medieval town of Etruscan origins and one of the most charming hilltop villages in the Chianti.
Monteriggioni with its walls and the ring of towers that dominate the hill.
Chianti Classico wine tour and tasting with lunch in local winery before to come back to Siena.
You’ll be back to Siena riding the Montagnola Senese region, crossing the road of the Via Francigena pilgrimage route.

Dinner and accommodation in hotel.

4 Ottobre - 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 reach the Castle of Brolio, real symbol of Chianti region, 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.
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 in hotel.

5 October - L'Eroica

Early wake up early private transportation to Gaiole in Chianti to participate at the 2022 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.

6 October - Arrivederci

Breakfast and individual departures.

Airport or train station transfer available on request with extra charge.

WHAT'S INCLUDED

7 Nights stay with breakfast
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 2025 (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 29th
Wool bike jersey of Anima Toscana

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: carbon road bike, vintage bike
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

2580,00 €
*Tour and prices guaranteed with a minimum of participants.

LODGING

HOTEL CASANOVA

Typical Tuscan structure that blends in perfectly with the nature that surrounds it, where absolute peacefulness is perceived, and that offers an all-round panorama of the Val d'Orcia and the medieval village of San Quirico d’Orcia, located at just a short distance from the Hotel.

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BORGO GRONDAIE
Borgo Grondaie is a large property built out of an old Tuscan farm, just 2 km from the historical centre of Siena. It offers an outdoor salted-water pool, and room and apartment accommodation of various sizes with free WiFi, furnished in rustic Tuscan style
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