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A family bike tour in Tuscany doesn’t have to come with sacrifices. With DIGnGO, you don’t need to worry about the planning, we take care of all the details. You cycle through the Val d’Orcia, the Val di Chiana and the Chianti wine region. You visit Siena, Montepulciano and Montalcino. And you learn the art of pasta making. All you have to do is look out on a rolling Tuscan countryside as thoughts of regional Italian cuisine fill your mind. A Tuscany bike trip with your family is simply amazing!
6 Days / 5 Nights
Firenze Santa Maria Novella Train Station
Chiusi Chianciano Terme Train Station
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Your family cycling vacation in Tuscany starts in the city of Florence, the center of early Renaissance art and architecture. From the train station, transfer to Castellina in Chianti, a small town in the Chianti Hills. There, enjoy a light lunch and introduction to the week. Before getting on your bike, stroll through the town. Feel free to explore the church of San Salvatore and walk through the Via Delle Volte, an underground tunnel with shops and artisans. Then, ride through the Chianti Hills to your hotel, the Villa Curina Resort.
Today’s Ride: 23 miles with 1,600 feet of climbing
On your second day, ride through the Chianti wine region, famous for the Chianti wine, Italy’s most famous wine. Spin through rolling hills on your way to Radda in Chianti, the capital of the Chianti Classico. On the way, stop at a local pottery store. Before lunch, stroll through the narrow streets and admire the tower building of this medieval town with large defensive walls. In the afternoon, spin back to your hotel on a nice route, passing by Lecchi in Chianti. Later, explore Siena, famous for its central square, the Piazza del Campo and its horse race, the Palio. You’re on your own for diner in town, however feel free to ask your leaders for recommendations.
Today’s Ride: 36 miles with 3,200 feet of climbing
Short Option: 17 miles with 1,600 feet of climbing
Long Option: 44 miles with 3,900 feet of climbing
This morning, depart for Asciano, a historical town at the foothills of the Crete Senesi. On the way and depending on the time of the year, admire the green rolling hills, typical of the Tuscan countryside. Arrive in Asciano just in time for lunch. In the afternoon, spin through the Crete Senesi or join the kids at an outdoor adventure park with tarzan swings, monkey bars, climbing walls and rope bridges. Enjoy the rest of the day as you like. Feel free to take a walk through the town of Montalcino, famous for the Brunello di Montalcino wine.
Today’s Ride: 31 miles with 2,300 feet of climbing
Short Option: 18 miles with 1,400 feet of climbing
Long Option: 38 miles with 3,600 feet of climbing
Enjoy a hearty breakfast and get ready for a challenging ride. Start with a nice descent into Castelnuovo dell’Abate, passing by the Abbey Sant’Antimo before a challenging ride between the villages of Monte Amiata and Castigliole d’Orcia. For lunch, take a break at the foot of Rocca d’Orcia, a fortress high above the Val d’orcia. In the afternoon, spin through the rolling countryside, passing by Monticchiello and arriving in Montepulciano and the Albergo Duomo, your hotel for the next two nights.
Today’s Ride: 33 miles with 3,800 feet of climbing
Short Option: 18 miles with 2,000 feet of climbing
Set out on a ride to nearby Pienza, the ideal Renaissance town and the birthplace of Pop Pius II. Pedal past Castelmuzio, an Etruscan village with a watch tower and ancient arched stone gate. Pass by the Monastery of S. Anna in Camprena, the setting of the oscar winning movie, the English Patient. Later on, arrive in Pienza, the most famous town in the Val d’Orcia. Don’t forget to sample Pecorino cheese as you stroll through town. In the afternoon, ride the cypress-lined Monticchiello road, a uphill stretch with beautiful cypress trees. If you prefer, join the kids for a cooking class and pasta making lesson. In the evening, celebrate with a gourmet dinner.
Today’s Ride: 31 miles with 3,300 feet of climbing
Short Option: 18 miles with 1,500 feet of climbing
Long Option: 37 miles with 4,000 feet of climbing
Your family cycling vacation in Tuscany ends at the Chiusi Chianciano Terme train station.
Wow…we just got back from a wonderful bike trip to Tuscany with Doug and Robbie. We were blown away by the flexibility of our guides, the personal service, the lovely hotels, fantastic and interesting meals and beautiful countryside. This bike trip was customised for our family and we had a variety of levels of bikers and we all had a great time. A trip of a lifetime!
Thank you very much for a great cycling experience. From early morning to late at at night, you were with us to make our vacation a special experience. Thank you for everything.
I would like to send our family’s best recommendation to anyone who will join your tours. Our family trip to Tuscany in April was just amazing. We received excellent support by Sam and Simon. We will never forget! We certainly would like to join DIGnGO tours again!
Thank you for everything. Send all our best regards to Sam and Simon.