Spend a week savoring Tuscan roads, food, and wine: from the Val d'Orcia UNESCO protected site, via Crete Senesi and Chianti area, visiting some of the most enchanting medieval towns like Pienza, Montalcino and Siena.
The Tuscany Bike Tour will be a special combination of the classic Heart of Tuscany enriched by some spectacular rides, taste the fantastic tuscan dishes and world famous wines like Brunello di Montalcino and Chianti Classico.
Discover by bike all that Tuscany has to offer, with the people who know it best.
On the first part of the week you will cycle surrounded by the beautiful landscape of Val d’Orcia, UNESCO protected site, and you can visit some nice towns including Pienza, Montepulciano and Montalcino.
On the second part you will cycle through the Crete Senesi region to Chianti, famous for its wine.
DURATION: 7 days/6 nights
PRICE PER PERSON IN DOUBLE ROOM: from 2980,00 €
WHERE: Val d'Orcia - Crete Senesi - Chianti
DATES: private request from April to November
SCHEDULED DATES 2025: 28 April-4 May | 8-14 September | 13-19 October
Itinerary
1
Day 1 - Benvenuti in Toscana
Meet our staff in Siena and private transportation to Hotel Casanova, typical Tuscan hotel that offers an all-round panorama of the Val d'Orcia and the medieval village of San Quirico d’Orcia, at just a short distance from the Hotel.
Check-in into your room and welcome aperitif to introduce the Tuscany Bike Tour before the first delicious dinner in typical restaurant of San Quirico d’Orcia.
2
Day 2 - Pienza, Montepulciano and Monticchiello
56 km – Elevation gain: 910 meters
The landscapes of the 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, Bagno Vignoni, a small medieval village developed around its hot springs that were used by the Romans centuries before - Take a relax break from the cycling journey before dinner.
Dinner and accommodation at Hotel Casanova.
3
Day 3 - Montalcino and Bagno Vignoni
53 km – Elevation gain: 990 meters
Climbing towards Castiglione d’Orcia and Rocca d’Orcia, the beautiful landscapes will compensate the challenging ascent - We'll reach the Brunello region and visit the Abbey of Sant’Antimo, one of the most beautiful romanic church in Italy - Wine tour and tasting in a Brunello winery before to climb up to Montalcino - Visit of Montalcino, medieval town surrounded by vineyards and beuatiful view on the valley - Back to San Quirico d'Orcia and rest ot the day in relax.
Final dinner in Val d'Orcia before the Chianti region.
4
Day 4 - Crete Senesi region
60 km – Elevation gain: 980 meters
An unforgettable ride surrounded by the views of the Crete Senesi to the edge of the Chianti - The Crete Senesi region, where badlands and biancane characterize the landscape in this part of Tuscany - A short break at Asciano with its churches and museums - 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. - Light lunch along the route and final arrival in Siena.
Dinner in local restaurant and accommodation at Hotel Athena.
5
Day 5 - Chianti region and Castello di Brolio
60 km - Elevation gain: 1160 meters
Tour loop to discover the Chianti wine region and Castello di Brolio.
In the first part of the stage you’ll leave Siena and reach the Chianti region at Geggiano and Pievasciata, where you can discover also the Chianti Sculpture Park, a permanent exhibition of contemporary sculptures.
Castle of Brolio, symbol of Chianti and excellent wines to taste. Before to ride the second part of the tour you will have the opportunity to visit the Castello di Brolio, dating back to the 11th century and owned by the Ricasoli family since 1141.
Villa a Sesta and Castelnuovo Berardenga, little jewels in Chianti region.
Enjoy the famous Chianti Classico wine in one of the selected winery along the route before to come back to Siena, riding a mix of gravel and paved roads along the Eroica route.
Dinner in local restaurant and accommodation at Hotel Athena.
6
Day 6 - Monteriggioni and Castellina in Chianti
58 km - Elevation gain: 940 meters
Daily ride to discover Castellina in Chianti 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. - Duirng the ride we will stop in a winery for a Chianti Classico wine tour and tasting with lunch.
Back to Siena riding the Montagnola Senese region, crossing the road of the Via Francigena pilgrimage route.
Dinner in local restaurant and accommodation at Hotel Athena.
7
Day 7 - Arrivederci
Check-out and transportation at Siena train station. Other destinations available on request with extra charge.
Otherwise you can decide to add more days at your stay.
WHAT'S INCLUDED
- 6 Nights stay with breakfast in double room
- 6 Dinners, drinks not included
- Light lunch, wine tasting, cheese tasting and lunch included day by day
- Baggage transportation between the hotels
- Maps and information for your daily stage in PDF file
- GPX tracks for GPS
- Van support during each stage
- Water and fresh fruits for your daily ride
- English speaking guide
- Bike rental for 5 days
- Private transfer on day 1 and 7
- Anima Toscana bike jersey
NOT INCLUDED
- Tourist city tax
- Drinks
- Medical insurance
OPTIONAL SERVICES (PRICES ON REQUEST)
- Medical insurance
- Flights
- Activities for non-cyclist (cooking class, truffle hunting, guided tours, horse back riding, trekking...)
PRICE PER PERSON IN DOUBLE ROOM
2980,00 €
*Tour and prices guaranteed with a minimum of participants.
*Tour and prices guaranteed with a minimum of participants.
LODGING
HOTEL CASANOVA
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HOTEL ATHENA
Hotel 4 stars located in the town center of Siena, very close Piazza del Campo and the Duomo di Siena. The perfect place to enjoy Tuscany by bike.
Visit the web site
HOTEL ATHENA
Hotel 4 stars located in the town center of Siena, very close Piazza del Campo and the Duomo di Siena. The perfect place to enjoy Tuscany by bike.
Visit the web site
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