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Self-Guided Bicycle Tours in Italy: Cycling Southern Tuscany: Lucignano to Chianciano Terme

Southern Tuscany is the poor step-daughter of Central Italy dressed up in pearls and emeralds. The soils here are arid clay but the occasional outcropping of volcanic soils allows for pockets of fine wines in places like Montepulciano and Montalcino. Pedal through the stark, though beautiful Val d'Orcia, the valley of the Orcia River near Pienza and San Quirico. Visit the Medieval Monastery of Monte Oliveto Maggiore in the famous, eroded Crete Senesi, and enjoy gelato in the ancient Etruscan town of Cortona. This is the Tuscany of flaming cypress trees on the ridgeline and lonely shepherds grazing their flocks after the wheat harvest. Enjoy a loop ride into Siena.

Day 1: Arrive in Medieval Lucignano Today

Highlights: Perfectly preserved Medieval village

Lucignano is unique in Italy as it preserves the nearly perfect oval shape of the typical 13th century Medieval village. Your hotel is in the center of this historic settlement. Plan to arrive mid afternoon as we'll fit bicycles around 4 p.m. so you'll have time to go out for a short ride to the nearby town of Monte San Savino, famous locally for its ceramics. This evening you'll want to stroll through Lucignano and say hello to your neighbors. Daily Mileage: 18 km (11 miles).

Day 2: Bicycle to Cortona

Highlights: Val di Chiana (Valley of the Chiana River) and Cortona

Today's loop ride takes you to the town of Cortona, once a major Etruscan settlement across the valley of the Chiana River. Take time to explore the modern Etruscan museum in the main square in Cortona and to have ice cream (gelato) at our favorite gelateria. Your loop take you back to Lucignano through Foiano della Chiana. Daily Mileage: 60 km (37 miles).

Day 3: Cycle from Lucignano to Asciano

Highlights: Sinalunga, Asciano and the Crete Senesi

You leave Lucignano by bicycle today for Sinalunga and Trequanda on your way to Asciano, located in the midst of the unique "Crete Senesi." This unusual geographic area is comprised of eroded clay deposits that support simple wheat farming and sheep grazing. The ridge tops are often marked by the famous Tuscan cypress trees. Asciano is another well-preserved Medieval village with the 14th century walls, built by the Sienese, still encompassing the town. Daily Mileage: 44 km (27 miles).

Day 4: Loop Ride to Siena

Highlights: Crete Senesi, Siena

We suggest pedaling to Siena and back today so you can visit one of Italy's major Renaissance attractions. Alternatively, trains are frequent and accept bicycles so you could pedal one way and take the train the other (or, if you'd like a day off the bikes take the train both ways). There are also many roads to explore around Asciano if you'd prefer to ride rather than visit Siena. Daily Mileage: Your choice up to 70 km (43.5 miles) if you ride to Siena and back.

Day 5: Asciano to San Quirico d'Orcia

Highlights: Monte Oliveto Maggiore, Val d'Orcia, San Quirico d'Orcia

Heading south you'll follow the "Crete" to the famous Abbey of Monte Oliveto Maggiore. This is one of the most important religious sights in all of Tuscany. The first American bicycle tourists in Italy, Joseph and Elizabeth Pennell rode their tandem tricycle here in October of 1884 and spent several days as guests of the Abbey. Unfortunately they don't take guests any more but you should plan to stop and visit anyway. The Abbey has frescoed walls, an historic library and a Renaissance era pharmacy. Your ride ends in San Quirico d'Orcia today, overlooking the Orcia River Valley. Daily Mileage: 40 km (25 miles).

Day 6: San Quirico d'Orcia Loop Ride

Highlights: Montalcino, Sant'Antimo Monastery, thermal spa of Bagno Vignoni

You can spend the day by the pool (depending on the month) or you can enjoy a loop ride to the Roman spa of Bagno Vignoni and on to Castiglione d'Orcia and Montalcino. This latter village is one of Tuscany's most famous wine towns, known for its "Brunello di Montalcino." On this route you'll pedal past the solitary Benedictine Abbey of Sant'Antimo amidst the olive trees. The Abbey was founded by Charlemagne in the late 8th C., abandoned in the 13th C., and reclaimed by the Church after 1870. Arrive here during vespers on a quiet morning and you'll be struck by the genius of the place. Daily Mileage: 52 km (32 miles).

Day 7: Bicycle from San Quirico d'Orcia to Chianciano Terme

Highlights: Pienza, Montepulciano and the Val d'Orcia

Your ride today takes you to two of the most famous destinations in southern Tuscany: Pienza a small village made into a Renaissance gem by Pope Pius II and Montepulciano, famous for its "vino nobile," a red wine made from the Sangiovese grape. Plan at least on coffee in Pienza and, maybe, picking up picnic supplies for a lunch on the road. Alternatively you can have lunch in Montepulciano. The shops in both towns feature savory "wild boar sausage" and local "pecorino romano" cheeses of varying ages. Your ride today affords views over the expansive and barren Orcia Valley, save the soaring cyprus trees along the ridge tops. Your hotel this evening is in Chianciano Terme, one of many small thermal spas found in Tuscany. Daily Mileage: 40 km (25 miles).

Day 8: Tour ends in Chianciano Terme


Your tour ends today. Stay and relax for another day or head on to Florence or Rome to join the tourist circuit. The main train line will take you north or south. Enjoy your remaining time in Italy!
  • Highlights
    The Medieval village of Lucignano, Cortona, Renaissance Siena, The Abbey of Monte Oliveto Maggiore, Wine towns of Montalcino and Montepulciano , The planned Renaissance town of Pienza, Bicycle the UNESCO World Heritage Landscape of the Val d'Orcia
  • Includes
    7 nights accommodation in 3 or 4 star hotels; 7 breakfasts; use of a quality 24-27 speed racing or hybrid bicycle); detailed route descriptions; map; optional rides daily; suggestions for dinners and lunches; luggage transfers
  • Countries
  • Begin/End
    Lucignano/Chianciano Terme
  • Arrive/Depart
    Rome, Florence or Bologna
  • Total Distance
    324 km or more by choice (201 miles)
  • Daily Distance
    0 to100 km (0 if you don't ride on rest days)
  • What to Expect
    Hill rides through olive groves, vineyards, Medieval and Renaissance towns and villages; lots of extra rides for those who can't get enough
  • Rating
    Medium level rides for those in moderate shape; aggressive extra rides available for those who can't get enough
  • Notes
  • Terms
Dates Price Single
Begin any Saturday; A single supplement of 300 euros is applied for just one traveler alone. A single room supplement for cyclists traveling with others sharing a room is 200 euros for the week. €1225 250 Euros (singles traveling with others pay a 200 euro supplement) Request space on this tour now!

Click on the "pins" for details about each day's highlights.

Map Key

Green pinStart
Yellow pinCity (on route)
Red pinEnd
Other city dotCity (not part of route, provided for reference)
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