tuscany hill towns bike tour, central italy

Bike Tour Tuscany, Hilltown of Pienza

Day 1: Saturday - Cortona

Meet at the Cortona train station and transfer to hotel to set up bike and introduction to the week of riding.  

Day 2: Sunday - Cortona to Montepulciano

From the Cortona we head across the valley to Montepulciano, home of Vino Nobile – famed as “the king of wines” since the 8th century.
Destinations visited: Montefollonico & Montepulciano
Distance cycled:40.2 km/27.50 miles

Day 3: Monday - Montepulciano - Monticello - Pienza - Montepulciano

Embark on a loop ride to the town of Pienza, an architectural gem thanks to its namesake, Pope Pius II, who made it a pet project to turn his hometown into the ideal Renaissance city. The result is often described as the most beautiful village in Tuscany. In Pienza you will have time to meander the cobbled streets, practice your Italian at a local café, people watch, and taste the local wine-soaked or truffle-dusted pecorino cheese. Leaving Pienza, you’ll feel like you’re riding through a movie set, and you won’t be far from the truth. Gladiator and the English Patient were both filmed here. We’ll head past the monastery of Sant’Anna in Camprena and the villages of Castelmuzio and Petroio on cypress-lined roads.
Destinations visited: Montefollonico, Pienza, St. Anna in Camprena & Petroio
Distance cycled: 37 km/23 miles

Day 4: Tuesday - Montepulcaino - Montefollonico - Montalcino

Today it’s off to the land of the Brunello wines, renowned as some as the world’s finest. The cycling route is stunning, beginning with rolling terrain through pastures and forests on the way to the sleepy village of Montisi where we will ride down the medieval streets. After Montisi, enjoy the panoramic views stretching from Mt. Amiata to Chianti as you cruise past poppies and sunflowers down the ridgeline to San Giovanni D’Asso and along the Asso River valley to Torrenieri. The road to Montalcino takes us right past some of the most famous Brunello wineries, including Casa Nova Dei Neri. Upon arrival, we’ll check into your hotel, with Montalcino’s many cafes, wine bars and pizzerias there are plenty of places to eat lunch up to you. After lunch you can join our guides for the 18km roundtrip ride down to the Abbey of Sant’ Antimo to hear the monks chant a Gregorian mass or spend the afternoon exploring Montalcino or relaxing by the pool. Montalcino is a picturesque town famous not only for its Brunello wines, gourmet honey and pecorino cheese, but also for its outstanding medieval architecture.
Destinations visited: Montefollonico, Montisi, San Giovanni D’Asso, Torrenieri,
St. Antimo Abbey & Montalcino.
Distance cycled: Shorter Option: 40 km/25 miles. Longer Option: 58 km/36 miles

Day 4: Wednesday - Montalcino - Siena - Montalcino

Enjoy an early-morning stroll around town, a sunrise visit to hear the chanting at Sant’Antimo or sleep in before another gorgeous day of cycling through the Tuscan countryside. We’ll spin to the 14th century Abbey of Monte Oliveto Maggiore to visit its outstanding Renaissance frescoes. After a gourmet Tuscan picnic featuring local pecorino cheeses, prosciuttos, and pates, washed down with a suitable regional wine, you can choose to take the van directly to the hotel in Siena or continue riding. Riders will cruise along the bare ridges of the Crete Senesi through Asciano and Vescona to Arbia, where we will once again have the option to take the van to the hotel. For truly ambitious cyclists, the final 11 km to the hotel is a real treat as we follow timeless back roads up a series of challenging hills to enter Siena in truly evocative fashion. Siena is gem of a medieval city with beautifully preserved Gothic architecture. The city is built around the Piazza del Campo, regarded by many as the most beautiful piazza in all of Italy. Here you’ll have, time to shop while exploring the many hidden medieval walkways. The night is yours and your guides will be happy to point you to a favorite local trattoria for dinner.
Destinations visited: Abbey of Monte Oliveto di Maggiore, Asciano, Vescona, Arbia
Distance cycled: Shorter Option: 22 km/14 miles. Standard Option: 52.5 km/32.50 miles. Longer Option: 64km/40 miles.

Day 5: Thursday - Montalcino - Siena – Radda in Chianti

From our hotel, we’ll transfer to Arbia, and then ride deep into the hills of Chianti. Passing rows of olives and cypresses, we’ll climb a ridge and break out of the trees as we ride through the gorgeous Chianti Classico estates of Bossi and San Felice before continuing to the Castello di Brolio. A Tuscan landmark for 1000 years, this imposing castle and the surrounding vineyards were given a facelift in the 19th century by the stern Baron Ricasoli who not only modernized local winemaking, but served as one of Italy’s first prime ministers.
Destinations visited: Arbia, Monteaperti, Castello di Brolio & Radda in Chianti
Distance cycled: 40.5 km/25 miles

Day 6: Friday -  Radda – San Gimignano - Florence

On the last morning, ride through the hills of Radda and Castellina on your way to visit San Gimignano, with its beautiful medieval towers and frescoed church of Santa Fina, a local saint. Shop for linens, ceramics, hand carved wooden ornaments, or perhaps a cycling jersey with the Chianti Classico black rooster. Be sure to stop at the gelateria in the main piazza, international gelato champions. After San Gimignano the ride continues on to Florence where we will end our tour.
Destinations visited: San Gimignano and Florence
Distance cycled: 50 km/31 miles

TRIP TOTAL: 250.9 KM/ 145 MILES, averaging 40-50 km/ 25-30 miles per day. Optional longer rides available each day.
Tuscany is hilly. The Tuscany Hilltowns Ride is a strenuous bike tour, and you will have several challenging riding days. You do not have to be an expert rider but you need to enjoy the challenge of hills, and be healthy.

This is a suggested tour option, if you are interested in doing this tour as a private trip or modified to fit your riding needs contact: McClure's Bike Italy

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