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 A 5 or 8 days cycling tour in Tuscany


 This tour starts and finishes in the beautiful and fascinating town of Siena. You will pedal in one of the most famous landscapes of Italy: the Val d’Orcia and Val d’Elsa. This land is full with enchanting towns where there is a merging of unspoilt nature, marvellous art and the pleasures of excellent cuisine. You will cycle along good dirt roads and quiet asphalted country roads between fertile fields, woodland and the vineyards of the Chianti area. You will have time enough to admire the art towns Pienza, Montalcino, Volterra and San Gimignano, abbeys with a glorious past like the abbey of Monte Oliveto and S.Anna a Camprena with its frescoes of Il Sodoma and the castle of Brolio.







Day 1

Individual arrival in Siena.

Siena is a town we could call a masterpiece of art, full of treasures such as the cathedral with the Piccolomini Library and its frescoes by Pinturicchio, the cathedral museum ‘Museo dell'Opera del Duomo’, the ‘Museo Civico’, the ‘Palazzo Pubblico’ ,a lot of other impressing palaces and churches…and the Piazza del Campo. It is also well known for the Palio, the most famous historical horse race in the world, and for its culinary tradition with delicious plates as ‘i pici’, la zuppa ribollita served on toasted bread and cakes like Panforte, Berricuocoli and Ricciarelli. Overnight stay in Siena.


Day 2

Siena – Brolio – Castelnuovo Berardenga – Asciano

After breakfast you leave Siena and cycle surrounded by a beautiful scenery of the hills of the Chianti Senese and le Crete with unforgettable panoramas of the Chianti vineyards and woodland. Worthwhile to visit is the castle of Brolio, surrounded by vineyards, which has Lombard origins. The tour of today finishes at Asciano. It has a nice medieval centre with a famous museum: the Museo Archeologico of Palazzo Corboli is classified by the Daily Telegraph as one of the fifteen Italy’s best small museums.

Distance 49 km / 30,4 miles –differences in altitude 830 m– 13km of dirt roads


Day 3

Asciano – Monte Oliveto – San Giovanni d’Asso - Pienza 

Today you enter the Val d’Orcia with wide open skies, rolling hills lined with cypresses and meandering roads disappearing into the horizon. You pass the abbey of Monte Oliveto with its chiostro (cloister) decorated by Luca Signorelli and il Sodoma, the church renovated in Baroque style and the beautiful library. You can plan to make a stop in the medieval village of San Giovanni d’Asso, where you could visit the truffle museum. Another stop worth while is at the ex- monastery of S.Anna a Camprena, where other frescoes of Il Sodoma can be admired. Pedalling between fields with nice views you arrive at Pienza, a pearl of the renaissance.

Distance 52 km / 32 miles –differences in altitude 800 m– 12km dirt roads


Day 4

Pienza – S.Quirico – Montalcino – Buonconvento – Murlo 

A scenery with soft rolling hills, never ending grain fields, vineyards, olive groves, hay meadows and pastures for livestock will accompany you all day. Very interesting is the historical centre of S.Quirico d’Orcia with its 13th century hospital of S.Maria della Scala. This hospital offered shelter to pilgrims and travellers passing along the Via Francigena. The other two charming towns you will pass today are Montalcino, where you can enjoy a good glass of Brunello di Montalcino, and the medieval village of Murlo.

Distance 56 km / 34,7 miles –differences in altitude 750m– 15km dirt roads


Day 5

Murlo – Radi – Sovicille – Monteriggioni – Colle Val d‘Elsa  

Today’s ride is following for a big part the Via Francigena, a pilgrimage way which in 79 stages connects Canterbury with Rome, crossing France and Switzerland before entering in Italy. Already from afar you will see the impressing town walls of Monteriggioni. These walls are covering a length of 570m alternated by two town gates and 14 towers. Here you could make a lunch stop to taste some of the local specialities like Panzanella, la Finocchiona and baccelli, funghi in gratella (mushrooms) and l’agnello arrosto con piselli e patate alla ghiotta (lamb meat with peas), combined with a good Chianti. Your overnight stay will be in Colle Val d’Elsa.

Distance 64 km / 39,7 miles –differences in altitude 680m–mixture of dirt roads and asphalted roads


Day 6

Colle Val d’Elsa – Casole d’Elsa – Ulignano – Volterra

Some uphill and downhill cycling will bring you to Volterra, an Etruscan town famous for its alabaster production. From Etruscan times remain the two town gates Porta all’Arco and Porta Diana and numerous tombs. In the centre you can visit 4 museums: the Museo Etrusco, Pinacoteca Civica, Museo d'Arte Sacra and l'Ecomuseo dell'Alabastro.

Distance 47 km / 29 miles – differences in altitude 1110m– mixture of dirt roads and asphalted roads


Day 7

Volterra – Il castagno – San Gimignano - Certaldo (transfer by train to Siena)

This last day you will cycle to San Gimignano, famous all over the world for the skyline of its medieval towers. This town dominating the Valle d’Elsa was very important during medieval times because of its position along the Via Francigena. In the surrounding countryside we find the cultivation of saffron. By bike you will reach Certaldo and from here you take the train to Siena, end destination of this tour.

Distance 47 km / 29 miles – differences in altitude 600m– mixture of dirt roads and asphalted roads


Day 8

Departure after breakfast




This tour has also a 5 day version:

Day 1 Individual arrival in Siena.

Day 2 Siena – Brolio – Castelnuovo Berardenga – Asciano (48 km / 29, 8 miles)

Day 3 Asciano – Monte Oliveto – San Giovanni d’Asso - Pienza (52 km / 32,2 miles)

Day 4 Pienza – S.Quirico – Montalcino – Buonconvento – Murlo (55 km / 34,1 miles)

Day 5 Murlo – Siena, the tour ends in the afternoon (46 km / 28,5 miles)




Included in the price:

  • Standard version 8 days: in *** star hotels and one night in **** star hotel; Deluxe version 8 days **** hotels and 1 night in *** star hotel with swimming-pool in superior room

  • Standard version 5 days: accommodation in 3 star hotels; deluxe version 5 days: 3 nights in 4 star hotels and 1 night in 3 star hotel with simming-pool in superior room

  • breakfast

  • luggage transportation

  • Road book with English route instructions and maps

  • Service-Hotline

Not included in the price:

  • 8 day tour: the train ticket from Certaldo to Siena in the 8 day tour

  • Local tourist taxes



Standard version: daily from 1st March to 15th October; deluxe version from March 28th to October 10th. During the Palio the tour might not be available

Level 3

typical hilly landscape with uphill and downhill cycling. There are sometimes steep climbs, but short. For the biggest part you’re cycling on quiet dirt and asphalted roads. The dirt roads (5-15 km every day) are in a good condition. Daily rides are between 40 and 60 km A tour for cyclists with some experience.


Minimum two persons (single traveller on request)

Prices p.p. 2020

8 day Standard Tour

In double room     € 750,00

In single room € 930,00

High season supplement  (10/04-31/08)  € 40,00

Bike rental    € 135,00

Ebike rental   € 250,00

8 day Deluxe Tour

In double room     € 850,00

In single room € 1.095,00

High season supplement   (10/04-31/08)  € 45,00

Bike rental    € 135,00

E-bike rental  € 250,00

5 day Standard tour

In double room     € 465,00

In single room    € 595,00

High season supplement    (18/04-31/08)  € 30,00

Bike rental    € 110,00

E-bike rental  € 170,00

5 day Deluxe tour

In double room     € 510,00

In single room    € 655,00

High season supplement   (18/04-31/08)  € 30,00

Bike rental    € 110,00

E-bike rental  € 170,00

On request

Extra nights in Siena, Pienza