1.888.883.7948 [email protected]
1.888.883.7948 [email protected]

Tuscany Bike Tour

(10 Reviews)
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Why Book With Us?

  • Best value for your money
  • Groups limited to 14 guests
  • Family Business

Got a Question?

Do not hesitate to contact us. Our travel advisors will be glad to answer any questions you may have.


[email protected]

Fuji Absolute 1.1 Disc

6 Days / 5 Nights
Availability : April to October


If you’ve ever imagined of traveling through beautiful Tuscan countryside and discovering Toscana, we invite you to explore Tuscany on a DIGnGO bike tour. Cycle in the Val di Chiana amid incredible hilltop towns. Bike in the Val d’Orcia through spectacular vineyards. And go riding through an infinite sea of olive groves in Chianti. Join a DIGnGO cycling vacation in Tuscany today!


  • Apr 5 - Apr 10, 2020
  • Apr 12 - Apr 17, 2020
  • Apr 19 - Apr 24, 2020
  • Apr 26 - May 1, 2020
  • May 3 - May 8, 2020
  • May 10 - May 15, 2020
  • May 17 - May 22, 2020
  • May 24 - May 29, 2020
  • May 31 - Jun 5, 2020
  • Jun 7 - Jun 12, 2020
  • Jun 14 - Jun 19, 2020
  • Jun 21 - Jun 26, 2020
  • Jun 28 - Jul 3, 2020
  • Jul 5 - Jul 10, 2020
  • Jul 12 - Jul 17, 2020
  • Jul 19 - Jul 24, 2020
  • Jul 26 - Jul 31, 2020
  • Aug 2 - Aug 7, 2020
  • Aug 9 - Aug 14, 2020
  • Aug 16 - Aug 21, 2020
  • Aug 23 - Aug 28, 2020
  • Aug 30 - Sep 4, 2020
  • Sep 6 - Sep 11, 2020
  • Sep 13 - Sep 18, 2020
  • Sep 20 - Sep 25, 2020
  • Sep 27 - Oct 2, 2020
  • Oct 4 - Oct 9, 2020
  • Oct 11 - Oct 16, 2020
  • Oct 18 - Oct 23, 2020

Don’t see your dates of travel or want to travel with your own group of friends? Contact us today!


Day 1

Your Tuscany bicycle tour starts in Chiusi, one of the most powerful city in the Etruscan league around the 7th century BC. Then, transfer to Villa Cicolina for an authentic Tuscan lunch. Toast to the week with a glass of Prosecco, a sparkling wine, in hand. Then, set out on a loop ride through the Chiana Valley on your way to Montefollonico, an authentic hamlet. Later, join a winemaker for a wine tasting of Vino Nobile di Montepulciano. In the evening, you have dinner at an authentic trattoria so make sure to try the famous Bistecca Fiorentina.

Today’s Ride: 18 miles with 1,800 feet of climbing

Day 2

On your second day, depart for Pienza, the ideal Renaissance town and the birthplace of Pope Pius II. On the way, pass by some of the most famous hilltop towns in the Val d’Orcia: Petroio and Castelmuzio. In Pienza, don’t forget to sample Pecorino Toscano, a ewe’s milk cheese. In the afternoon, continue on to Monticchiello. Ride through an uphill stretch, famous for its cypress tree road and surrounding countryside. Later, arrive at your hotel for an authentic cooking class and lovely dinner in the gardens of Villa Cicolina.

Today’s Ride: 35 miles with 3,600 feet of climbing
Short Option: 19 miles with 1,800 feet of climbing
Long Option: 42 miles with 4,300 feet of climbing

Day 3

Gather in the hotel breakfast room for a delightful breakfast. Make your way to Rocca d’Orcia, a little hamlet, once the capital city of the Val d’Orcia. You’re on your own for lunch but feel free to ask your trip leaders for recommendations. From Rocca D’orcia, embark on a brisk downhill and a moderately challenging uphill stretch. End the day at the Castello di Velona Resort, an 11th century fortress with 360 degree views on the Monte Amiata, Tuscany’s highest peak. Before dinner, go for a self-guided visit of the Abbey of Sant’Antimo, a benedictine monastery.

Today’s Ride: 28 miles with 2,900 feet of climbing
Short Option: 19 miles with 2,000 feet of climbing
Long Option: 38 miles with 4,300 feet of climbing

Day 4

Your bike trip in Tuscany continue son towards Montalcino, a town famous for the production of the Brunello di Montalcino wine. Begin with an invigorating ascent all the way to Montalcino and its 14th century fortress. Then, wind your way through the Crete Senesi, an area with untouched rolling hills. Ride along fortified villages and ancient farming complexes, all testaments to the area’s rich history. Finally, arrive at the Borgo San Felice, an authentic medieval hamlet and your hotel for the next two nights. In the evening, explore Siena, a UNESCO World Heritage Site famous for its medieval square, the Piazza del Campo.

Today’s Ride: 34 miles with 2,500 feet of climbing
Short Option: 25 miles with 1,500 feet of climbing
Long Option: 43 miles with 3,500 feet of climbing

Day 5

Take a final ride on extremely peaceful roads and over a chain of beautiful rolling hills. Head out to Radda in Chianti, the capital of the Chianti Classico. Stroll through the medieval town before lunch on your own within its defensive walls. In the afternoon, ride back to the Borgo San Felice for some downtime. On the way, stop at a local shop for a glimpse of some traditional painted Tuscan ceramics. Before dinner, join your leaders for a guided tour of vast cellars and tasting of Chianti wine. Then, celebrate with a dinner at your hotel gourmet restaurant.

Today’s Ride: 30 miles with 2,600 feet of climbing
Short Option: 17 miles with 1,400 feet of climbing

Day 6

Your bike tour in Tuscany ends in the heart of Florence, Italy.


Villa Cicolina

Montepulciano (2 nights)

Castello di Velona

Castelnuovo (1 night)

Borgo San Felice

San Felice (2 nights)

What's Included


  • All breakfasts, 1 lunch and 4 dinners
  • Multiple daily routes
  • A fully equipped bicycle: the Fuji Absolute
  • Garmin GPS with easy to follow directions
  • Handlebar bag, helmet and water bottle
  • 1 leader for every 5 guests
  • Snack & drinks during the day
  • Gratuities at hotels and restaurants
  • Guided tours, tastings and entrance fees
  • A leader offering minivan support
  • Luggage transfers
  • Porterage
  • Minivan transfers during the trip
  • Local guides and experts
  • An email a few days prior to your trip

Not Included

  • Transportation to & from pick-up/drop-off
  • Pre or post trip lodging
  • Minibar, massages, etc
  • Alcoholic beverages
  • Road bike or e-bike
  • Gratuities for your Leaders


Tuscany cycling map


10 Reviews
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Alisdair S.

Couple Traveller

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.

August 30, 2018

Colleen S.

Couple Traveller

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!

July 19, 2018

Dino M.

Solo Traveller

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.

July 18, 2018

David U.

Couple Traveller

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.

June 29, 2018

Joseph B.

Group Traveller

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.

May 1, 2018