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!


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Bike ride in Tuscany.


  • 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 24 - May 29, 2020
  • May 31 - Jun 5, 2020
  • Jun 7 - Jun 12, 2020
  • Jun 21 - Jun 26, 2020
  • Jul 12 - Jul 17, 2020
  • Jul 26 - Jul 31, 2020
  • Aug 2 - Aug 7, 2020
  • Aug 16 - Aug 21, 2020
  • Aug 23 - Aug 28, 2020
  • Aug 30 - Sep 4, 2020
  • Sep 13 - Sep 18, 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 unforgettable adventure in gorgeous Tuscany begins with your arrival by train in Chiusi. We transfer you seamlessly to nearby Villa Cicollina, where you start your vacation off properly with a sumptuous, but light Tuscan lunch – including authentic fare like bruschetta – and a toast with a glass of the region’s most refreshing sparkling wine, Prosecco. While you’re at the villa, be sure to take some time to admire the view from the terrace of beautiful neighboring Val di Chiana.

Leaving the villa you start the week with a nice a simple loop touring the surrounding area passing through the town of Montepulciano, the perfect picture of an authentic Tuscan town. The aristocratic families of the region once summered at this very destination, leaving their very own unforgettable stamp on the beautiful ceiling frescos, period artwork, and furniture.

Later that day, you join a local winemaker for a tasting and tour. Don’t forget to sample the signature Vino Nobile, as well as the Vin Santo.

Dinner is at an authentic trattoria in one of the villages nearby.

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

Day 2

Your second day in glorious Tuscany starts with a simple, but delicious breakfast before you prepare to bike your way from Villa Cicollina to nearby Pienza. On the way, you ride into nearby Petroio and Castelmuzio where you see Sant Anna in Camprena (where scenes of the Oscar-winning film The English Patient were filmed) before arriving in Pienza.

When you arrive in Pienza, you may choose a trattoria for lunch on your own before exploring the town in more detail. Beautiful Pienza is the birthplace of one of Tuscany’s most famous cheeses, Peccorino. It is also the birthplace of the illustrious Pope Pius II. Today, it is a shining example of a rustic town that exemplifies the ideal of the Renaissance period to this day.

In the afternoon, coast through the town of Monticchiello. Next, you must prepare for a truly lovely experience, as the following leg of this route takes you through a uphill stretch that is world famous for its beautiful cypress trees and surrounding countryside. If it looks familiar, it could be because it’s appeared in many movies and magazine photo shoots over the years!

Later, arrive at your hotel for an authentic cooking class and a sumptuous dinner in the gardens of your villa.

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

Your third day in Tuscany opens with another positively delightful breakfast before heading toward Montalcino, another local region well known for wine production. On the way there, you pass through the lovely town of Rocca D’Orcia, a little hamlet that has been considered the “capital city” of the Orcia Valley area for roughly 200 years. Its major claim to fame is the fact that it was used as a strategy center along the Via Francigena, the historically renowned road connecting Rome to France. The area on the whole is also famous for the production of Brunello, a robust and respected local wine.

In the afternoon, you embark on a brisk downhill coast followed by a moderately challenging uphill stretch, at the end of which you arrive at your lodgings for the night – Castello di Velona. Originally, this hotel was an 11th century fortress. Today, it’s not just a hotel, but also a prime location where you can enjoy a spectacular 360-degree view of the surrounding landscape, including Monte Amiata – Tuscany’s highest peak. Relax and enjoy the pool for a moment as well, before attending a robust meal at the hotel restaurant. Before dinner, you have the opportunity to visit the Abbaye of Sant antimo and listen to the resident monks engaging in a beautiful and relaxing round of Gregorian chanting.

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 fourth day in spectacular Tuscany begins with breakfast and an invigorating morning ascent up to the nearby town of Montalcino, where you’ll get the chance to experience an authentic 14th century fortress. From there, you spend some time exploring the Crete Senesi (“Sienese clay”), an area that is characterized by the best of untouched Tuscany at its best including hills, words, a semi-desert, and surrounding waters – all once covered by the neighbouring sea many years ago.

Along the way you enjoy a refreshing light lunch on your own before continuing to explore the neighbouring area. Take in more of the nearby Sienese hills, as well as a number of landmarks that will emerge at random as you go. These include fortified villages, charming parish churches, and even ancient farming complexes – all testaments not only to the area’s rich history, but to the accomplishments man is capable of.

Finally, you arrive at your hotel for the next two nights – the Borgo San Felice, a location consisting of an authentic medieval hamlet, as well as a chapel.

Evening brings with it an opportunity to explore the town of Siena. Siena is built around the famed Piazza del Campo, one of Europe’s most noteworthy medieval squares. Legend says that it was founded by the sons of Romulus and Remus themselves, the founders of Rome.

Tonight’s dinner is on your own, so as you walk through town look out for a restaurant or ask your leaders.

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

Your final day in Tuscany presents you with an opportunity to experience the area’s most famous wine-producing area, Chianti. You ride your way over a chain of beautiful rolling hills and through a progression of refreshingly, peaceful local roads before arriving in Radda in Chianti, the capital of Chianti Classico. On the way, make sure to stop at a local shop for a glimpse of some traditional painted Tuscan ceramics.

Later, cruise your way back to the Borgo San Felice for an afternoon Chianti tasting in the cellars of your hotel.

Bring your vacation to a fitting close with dinner at the hotel’s gourmet restaurant but also with some terrific shopping and playful exploration of the many, hidden medieval walkways here.

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

Day 6

Enjoy breakfast at the hotel Borgo San Felice one last time before meeting up with your trip leaders. From here, a short drive to the Firenze train station marks the end of the tour and of this unforgettable trip through Tuscany.


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