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Tuscany adventure
Siena-Asciano-Pienza-Montalcino-Murlo-Colle Val d’Elsa-Volterra-San Gimignano
A stunning cycle tour through the best of TUSCANY: Art towns, sunny hills covered with vineyards, and excellent food! This tour starts and finishes in the beautiful and fascinating town of Siena. The historic city is listed as a world heritage site by UNESCO and is full with beautiful and interesting places to visit. Siena’s beating heart is the central piazza known as Il Campo. Here the worldwide famous Palio, a horse race between the different quarters of town, is held every year. The Campo is dominated by the red Palazzo Pubblico and its tower, Torre del Mangia. Along with the Duomo of Siena, the Palazzo Pubblico was also built between 1297 and 1310. If you feel yourself energetic, then climb up the 500 steps and youwill reward with a wonderful view over Siena and its surroundings. Do not forget to visit the Civic Museum of Siena that contains one of the world’s most famous allegories painted on the walls: the Bad and the Good Government by Ambrogio Lorenzetti.
You will pedal in one of the most stunning landscapes of Italy: the Val d’Orcia and Val d’Elsa. This land is full with enchanting old towns, unspoilt nature, marvellous art monuments and it is a place to enjoy the pleasures of an excellent cuisine and important wines. You will cycle along well-paved dirt roads and quiet asphalted country lanes between fertile fields, woodland and among the vineyards of the Chianti area. The Chianti area is one of the most attractive areas of Tuscany, a appreciated by visitors from all over the world. The beauty of its landscapes inspired many photographs that became postcards and calendars distributed across the globe.
You will have time enough to admire the art towns of Pienza, Montalcino, Volterra and San Gimignano, and abbeys with a glorious past like the abbey of Monte Oliveto and S.Anna a Camprena, where the frescoes of Il Sodoma can be admired and the castle of Brolio.
The daily program of the 5-day tour
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 with breakfast in Siena
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.
Overnight with breakfast in Asciano
Distance: 49 km / 30,4 mi
Ascent: + 830m
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.
Overnight with breakfast in Pienza
Distance: 52 km / 32 mi
Ascent: + 800m
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.
Overnight with breakfast in Murlo
Distance 56 km / 34,8 mi
Ascent: + 750m
Back to Siena and end of tour in the afternoon without overnight stay
Distance: 45 km / 28 mi
The daily program of the 8-day tour
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 with breakfast in Siena
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.
Overnight with breakfast in Asciano
Distance: 49 km / 30,4 mi
Ascent: + 830m
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.
Overnight with breakfast in Pienza
Distance: 52 km / 32 mi
Ascent: + 800m
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.
Overnight with breakfast in Murlo
Distance 56 km / 34,8 mi
Ascent: + 750m
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.
Overnight with breakfast in Colle Val d’Elsa
Distance: 64 km / 39,7 mi
Ascent: + 680m
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.
Overnight with breakfast in Volterra
Distance: 47 km / 29 mi
Ascent: + 1110m
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.
Overnight with breakfast in Siena
Distance: 47 km / 29 mi
Ascent: + 600m
Departure after breakfast
Impressions of Tuscany
Siena-Asciano-Pienza-Montalcino-Murlo-Colle Val d’Elsa-Volterra-San Gimignano
LEVEL 3
Typical hilly landscape with uphill and downhill cycling. There are sometimes steep climbs, but short. For the biggest part, you are 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 experienced cyclists with a good physical condition.
Total km: About 202 km / 125 mi (5- day tour) and about 315 km / 195 mi (8- day tour)
DEPARTURES:
Daily from 1 March to 15 October 2025. Note that in 2024 the Palio in Siena is 02/07 e
16/08. It is more difficult to find availability and a supplement can be asked by the hotel
(price on request). During the Palio the tour might be not available.
PARTICIPANTS:
2 or more people.
START / FINISH:
Siena / Siena
Umbria & Tuscany: in the footsteps of the Etruscans and Romans
An evocative bicycle tour through the Etruscan and Roman heartlands of Umbria and Tuscany, land of art, nature, food & wine.