Self-Guided Bicycle Tours in Italy: Bicycle Cortona, Montepulciano and Montalcino in Southern Tuscany Tour Itinerary

The Facts | Full Itinerary | Interactive Map

Day 1: Arrive at Chiusi/Chianciano Train Station, transfer to hilltop hotel

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Highlights: Fit bikes and take a warm-up ride amid the vineyards of Southern Tuscany
Arrive at the Chiusi Chianciano train station today early afternoon and we'll shuttle you to Borgo Tre Rose, your home for the next three nights. If your arrival time differs, please contact us and we will try to accommodate your travel schedule. We'll fit your bikes and suggest a short loop ride. Extra mileage is available all days. Dinner is at the hotel restaurant for the next 3 nights. Daily Mileage: 22 - 30 km (13.5 - 18.7 miles)

Day 2: Loop Ride to Cortona

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Highlights: Cortona, Etruscan Museum, gelato
We suggest a ride today to the Etruscan town of Cortona. You'll pass along the Val di Chiana, famous for the chianina steak bistecca di chianina before reaching the imposing town of Cortona on the top of the hill with its defensive Etruscan, Roman and Medieval walls surrounding the historic town. Cortona is an ideal stop for lunch and for some sightseeing. A must-see is the recently restored Etruscan Museum or the Museo Diocesano with Fra Angelico paintings. Our favorite gelateria is in the square in front of the museum. Daily Mileage: 50 km (31.2 miles)

Day 3: Loop Ride to Montepulciano

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Highlights: Medieval City Center, Vino Nobile di Montepulciano
Montepulciano is famous for the production of Vino Nobile di Montepulciano, and your ride today takes you there. After a stroll along the medieval streets of this village, you can stop to visit one of the typical wine cellars in town. Take time for lunch before returning to the hotel where the restaurant has prepared you dinner. Daily Mileage to Montepulciano: 31 - 44 km (19 - 27.5 miles)

Alternatively, you may choose to ride along the shores of Lake Trasimeno today. The lake is famous for Hannibal's defeat of the Roman army after crossing the Alps with elephants! Along the ride you'll pass close to the tiny Lago di Chiusi before reaching the fortified village of Castiglione sul lago. If you have the time you might want to take a boat ride on Lake Trasimeno to Isola Maggiore. After a stroll on the passeggiata and lunch on your own, continue back to Borgo Tre Rose. Daily Mileage to Lake Trasimeno: 34 - 44 - 54 km (21.2 - 27.5 - 33.7 miles)

Day 4: Bicycle to Pienza and San Quirico d'Orcia

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Highlights: Pienza and the UNESCO World Heritage Landscape of Val d'Orcia
Pack your bags and head to San Quirico D'Orcia today, your home for the next 3 nights. Luggage will be transferred directly to the hotel while your ride takes you to one of the first planned Renaissance towns, Pienza. With the help of a number of prominent architects Pope Pius II turned his small hometown into a piece of art in the 16th century. The Orcia River valley will be the focus for your rides over the next two days. Enjoy dinner in the hotel restaurant for the next 3 nights. Daily Mileage: 52 km (32.5 miles)

Day 5: Loop ride from San Quirico d'Orcia to Montalcino and the Abbey of Sant'Antimo

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Highlights: Montalcino, Abbey of Sant'Antimo, Bagno Vignoni
Pedal through vineyards and wheat fields this morning as you make your way to the Etruscan village and wine town of Montalcino. This fortified town was used as a shelter by Sienese nobles during the 16th Century, but today is even more famous for producing one of Italy's premier red wines, Brunello di Montalcino. Our scenic route takes you to the famous Abbey of Sant'Antimo and then on to Bagno Vignoni, a Medieval spa town. Daily Mileage: 54 km (33.7 miles).

Day 6: Loop ride to the Abbey of Monte Oliveto Maggiore

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Highlights: Trequanda, Abbey of Monte Oliveto Maggiore
Our loop route today takes you to Trequanda first and then to the Abbey of Monte Oliveto Maggiore, a Benedictine abbey built in the 13th century and famous for its frescoed cloister and stunning setting. You are back in San Quirico this afternoon in time for a swim or to enjoy the spa center of the hotel. Daily Mileage: 65 km (40.6 miles).

Day 7: Bicycle to Siena

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Highlights: Siena, beautiful southern Tuscan Landscape
The full beauty of the Tuscan landscape, from the lush green fields of the Orcia Valley to the barren, chalk hills of Central Tuscany, unfolds before you today as you leave San Quirico and pedal to Siena. Often described as Italy's best preserved medieval city, Siena rivaled Florence for dominance in Tuscany during the 1300s. You'll have time to take a leisurely stroll through this medieval art city this afternoon to visit Piazza del Campo, Torre del Mangia and the famous Duomo. There are a plethora of charming restaurants to choose from in the city center. Daily mileage: 58 km (36 miles).

Day 8: Tour ends in Siena

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Highlights: Enjoy Siena for another day or two
Your tour ends after breakfast this morning, but Siena is certainly worth another day or two. Trains are frequent and fast to Florence or south to Rome.