Southern Tuscany Bike Tour | 8 Days

From Pienza in the Val d'Orcia to Montalcino, the town of Brunello, and on to medieval Siena: an 8-day, 7-night cycling itinerary that crosses southern Tuscany from south to north.

Day 1 | Pienza

The Renaissance "ideal town"

Arrive at Chiusi-Chianciano station in the morning or early afternoon and make your own way to Il Chiostro in Pienza, your hotel for the next three nights.

Pienza was built almost in one go between 1459 and 1462, and it remains a rare example of Renaissance town planning. Its cobbled lanes are a joy to wander, and the town is also known for its food.

After collecting your bike, a bike fitting and a briefing on the daily routes, take a test ride to San Quirico d'Orcia, where you can stop at the town's highlight, the Horti Leonini gardens.

Distance: 22 km

Day 2 | Montepulciano and Monticchiello

Medieval streets and Vino Nobile

The day begins with a pleasant descent. Vineyards, cypresses and medieval villages make up the landscape where "The English Patient" was filmed, as you ride through the hilltop villages of Castelmuzio and Petroio.

Montepulciano is home to the red wine Vino Nobile di Montepulciano. After exploring its medieval streets, visit one of the town's traditional wine cellars: the oldest lies beneath Palazzo Ricci.

On the way back, you ride through the hilltop village of Monticchiello before returning to Pienza.

Distance: 53.5 km | Elevation: +1,068 m / -1,070 m

Day 3 | Trequanda, Montisi and San Giovanni d'Asso

To the land of the white truffle

After a descent of about 3 km, around 16 km of rolling roads bring you to Trequanda, one of the best-preserved medieval villages in the province of Siena. It grew up around a 13th-century castle, and its round tower with battlements still stands today.

Next comes Montisi, an old village linking the Crete Senesi and the Val d'Orcia. Enjoy the descent to San Giovanni d'Asso, world famous for its white truffles. Farmhouses, hamlets and castles dot a landscape with the colours of a Renaissance painting, and small hamlets lead you back to Pienza.

Distance: 54 km | Elevation: +791 m / -792 m

Day 4 | Bagno Vignoni to Montalcino

A spa village and the town of Brunello

Ride through Bagno Vignoni, a Tuscan spa village in use since Roman times, to Castiglione d'Orcia, crowned by the Rocca di Tentennano fortress.

A long descent takes you to the Abbey of Sant'Antimo. With a little luck, you may hear the monks singing Gregorian chant.

Ride on through magnificent vineyards to Montalcino, a wine town of Etruscan origin and your base for the next three nights. In the 16th century this fortified town gave refuge to the nobles of Siena; today it is known worldwide as the home of Brunello di Montalcino, one of Italy's great red wines.

Distance: 44.4 km | Elevation: +920 m / -876 m

Day 5 | The Abbey of Monte Oliveto Maggiore and the Crete

Postcard Tuscany

Today you ride through the classic Tuscan landscapes that make this one of the most photographed regions in Italy.

A scenic ridge road leads to the Abbey of Monte Oliveto Maggiore, a 13th-century Benedictine monastery known for its frescoed cloister and beautiful setting.

Then it's on to the Crete Senesi, sometimes called the "badlands of Tuscany", where green hills give way to rounded clay hills and an almost lunar landscape.

Distance: 47.3 km | Elevation: +781 m / -782 m

Day 6 | Sant'Angelo and Castello di Poggio alle Mura

An old castle and a great winery

Head to the Maremma side of Montalcino, stopping in the small village of Sant'Angelo before descending to Poggio alle Mura. Overlooking woods and vineyards, this medieval castle is said to date back to Etruscan times and grew considerably in the Middle Ages.

Today it is also known as Castello Banfi, the heart of a vast wine estate, with a museum of glass and wine, an enoteca and a taverna. On the way back you ride through the vineyards and can stop at a small Brunello winery.

Distance: 31 km | Elevation: +699 m / -700 m

Day 7 | Buonconvento, Murlo and Siena

To medieval Siena

The day starts with a descent of about 10 km, then heads north through Buonconvento towards Siena, on quiet roads and through more beautiful scenery.

In the village of Murlo you can visit the fascinating Etruscan museum. Via Ville di Corsano, you enter Siena through Porta San Marco.

Siena is often called the best-preserved medieval city in Italy, and in the 14th century it rivalled Florence for control of Tuscany. In the afternoon, take your time with Piazza del Campo, the Torre del Mangia and the Duomo. Twice a year Piazza del Campo hosts the Palio, the horse race contested by the city's 17 contrade (districts).

Distance: 55.2 km | Elevation: +880 m / -1,076 m

Day 8 | End of tour

An optional detour into the Chianti hills

The tour ends after breakfast. If you like, you can add an optional ride to Castello di Brolio in the Chianti region.