Uncover the best of Tuscany as you take an Italian bike tour on cypress-lined roads. We will explore the breathtaking landscapes of the Val d’Orcia and the Valdichiana, ride over the rolling hills of Crete Senesi, sample Chianti Classico in Chianti, and perfect our cooking skills with a local chef. With rolling hills, endless vineyards, and olive groves at every turn, Tuscany boasts incredible natural scenery. From breathtaking countryside and gorgeous terrain to beautiful hilltop towns and Renaissance palaces, a cycling vacation in Tuscany is the best way of experiencing « La Dolce Vita » (« the sweet life »).
Welcome to Tuscany, regarded as the birthplace of the Italian Renaissance. | Start your journey through Toscana with a light lunch served amid olive trees and flowers in the Tuscan garden of our hotel. | Enjoy authentic local specialties including bruschetta, Fettunta, and Tuscan Pecorino. | Bike through the Valdichiana past endless vineyards and olive orchards. | Pause at the Sanctuary of the Madonna di San Biagio. | Explore the medieval hill town of Montepulciano, home to the Santa Maria Assunta Cathedral. | Learn the nuances of Vino Nobile red wine with a local winemaker. | Gather at a local restaurant for typical Tuscan meal. | Pedal to Petroio and Castelmuzio, cruising by the monastery of Sant’Anna in Camprena, where scenes of the Oscar-winning film The English Patient were filmed. | Arrive in Pienza, known for its amazing UNESCO Historic Centre. | Spin into Monticchiello, an ancient village situated at the foot of an uphill stretch that is world famous for its beautiful cypress trees. | Relax while you take in the spectacular views from our hotel’s swimming pool. | A local chef invites us over for a private pasta making lesson.
Montepulciano | 3-star hotel
With just 11 rooms, Villa Cicolina embodies Tuscany with its rustic charms and fresh décor.
Ride through the rolling hills of the Val d’Orcia to the tiny hilltop village of Rocca d’Orcia, and the fortress of Rocca di Tentennano standing on a pinnacle high above the valley. | An exhilarating downhill ride followed by a challenging climb leads to our 5-star hotel, Castello Di Velona. | Admire the views of Mount Amiata, Tuscany’s highest peak, from the terrace of our hotel. | Take advantage of your hotel’s amenities including thermal spa, winery, and numerous pools. | Visit the Abbey of Sant’Antimo before enjoying a gourmet meal with spectacular views of the Val d’Orcia.
Castello Di Velona
Castelnuovo | 5-star hotel
The Castello Di Velona was built by a noble family during the Middle Ages. The hotel sits on a hill and offers amazing views over the rolling hills of the Val d’Orcia.
Take on the challenging climb to Montalcino, home to one of Italy’s most famous and prestigious wine, the Brunello di Montalcino. | Pass through the rolling hills of the Crete Senesi, an area often described as a « lunar landscape ». | Enjoy a lunch of local specialities at a restaurant in the town of Asciano. | Ease into an authentic medieval hamlet and our hotel. | Explore Siena, a medieval city known worldwide for the Palio di Siena, Italy’s most important horse race. | Stroll the medieval streets, lined with high-end boutiques, quirky gift shops, and traditional trattorias. | Set out on a ride through the dense vineyards of the Chianti, a region of Tuscany famous for its namesake red wine. | Hop off the saddle to explore Radda in Chianti, the capital of Chianti Classico. | Cycle through a region dotted with vineyards, chestnut forests, picturesque villages, and charming castles. | A wine expert invites us over for a cellar tour and tasting of some of the region’s best vintages. | Enjoy a farewell dinner at Michelin-starred restaurant, Il Poggio Rosso. | Head to Florence, the perfect place to extend your vacation in Tuscany.
Borgo San Felice
Castelnuovo | 5-star hotel
Situated in the beautiful medieval hamlet of Castelnuovo Berardenga, Borgo San Felice sits high on a hill among the vineyards and olive groves of the Chianti hills, not far from Siena.
See our booking form section on this page for all departure dates.
Get together with your traveling companions and share a great DIGnGO adventure. You can take over any of our guided tours and make it your own private cycling tour. If your departure date is not available, we’ll set a date for you, your family, and friends. Call us at 888-883-7948 to start planning your trip.
We’ll make it happen! Tell us what your ideal cycling experience would be and we’ll work closely with you to put it together. Our travel agents will arrange a bike trip that fits your needs, interests, schedule and budget. Call us at 888-883-7948 to speak with a custom tour manager.
We planned a trip together to enjoy the things that we both love – food, wine and travel.
After much research, you stood out relative to the other companies with your personalized approach, the nature of your trips, and the relatively small group sizes. You were very open and honest about questions put to you before we booked. You sold us with your honest and customer focused approach.
We couldn’t have asked for better customer service, attention to detail and special little surprises. We loved every hotel, every restaurant, and each day’s riding tour. You made sure, we had a special vacation.
We had an exceptional time and we highly recommend a trip with you. Upon our return to Canada, we received a very special photo album that captured our incredible memories.
Thank you – we will be back for another ride.
This cycling trip in Tuscany was the perfect first time experience for a bicycle tour for us. I’d like to try it again–maybe more suggestions next time!
The good – We had great leaders. Fun and attentive yet always professional, we came first. I always felt safe even being thousands of miles from home, knowing no one and unable to communicate due to language barriers. I really can’t stress how good they actually were.
You chose 5 star plus accommodations and restaurants. We used GPS which was a plus. We saw some other tours out with printed directions. I loved the GPS as I never went off course preventing me from wasting energy and time backtracking.
The bad – not much, but you really should explain that you should be in good enough shape. I am moderately athletic and ride for daily commutes and even I wish I had been more prepared. Overall, I loved it. You just better be ready and in shape for it.
We traveled with very friendly and likeable people. Made the bike tour always a pleasure and solved any problem promptly and courteously. Helping all the guests whenever a problem occurred. Generated a sense of belonging to the group.
We just wanted to let you know that we had a wonderful bike trip. You have excellent tour guides and we were lucky to have them. We arranged outstanding hotels and restaurants. We loved the cooking class and also enjoyed the wine tasting opportunities. Thank you again for a wonderful trip.