1.888.883.7948 [email protected]


Sign Up

After creating an account, you'll be able to track your payment status, track the confirmation and you can also rate the tour after you finished the tour.
Confirm Password*
First Name*
Last Name*
* Creating an account means you're okay with our Terms of Service and Privacy Statement.

Already a member?

1.888.883.7948 [email protected]


Sign Up

After creating an account, you'll be able to track your payment status, track the confirmation and you can also rate the tour after you finished the tour.
Confirm Password*
First Name*
Last Name*
* Creating an account means you're okay with our Terms of Service and Privacy Statement.

Already a member?


Tuscany Bike Tour

(10 Reviews)
Full Name*
Email Address*
Your Enquiry*
Save To Wish List

Adding item to wishlist requires an account


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

Home > All of Europe > Italy > Tuscany Bike Tour


Whether you’d like ride through the Val di Chiana, bike across the Val d’Orcia, cycle over the Crete Senesi or spin through the Chianti wine region, our bike tour of Tuscany is a sublime cycling adventure on cypress-lined roads. You explore Pienza, Siena, Montepulciano and Montalcino. You taste prized Brunello di Montalcino and white Montepulciano. You sample Pecorino Toscano. And you learn the art of pasta making. Join us today to do it all! Our Tuscany bike trip is a biking experience of a lifetime through lush olive groves and stunning vineyards.


6 Days / 5 Nights

Biking Level

Level 3

Pick-Up Location

Chiusi Chianciano Terme Train Station

Pick-Up Time

11.30 AM

Drop-Off Location

Firenze Train Station

Drop-Off Time

12.00 PM

Price Includes

  • All breakfasts, 1 lunch and 4 dinners
  • Multiple daily routes
  • A fully equipped bicycle: the Fuji Absolute 1.1 Disc
  • Garmin GPS with easy to follow directions
  • Handlebar & saddle bags, 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

Price Excludes

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


  • Apr 21 - Apr 26, 2019
  • May 19 - May 24, 2019
  • Jun 16 - Jun 21, 2019
  • Jul 21 - Jul 26, 2019
  • Aug 4 - Aug 9, 2019
  • Sep 29 - Oct 4, 2019

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


Villa Cicolina

Montepulciano (2 nights)

Castello di Velona

Castelnuovo (1 night)

Borgo San Felice

San Felice (2 nights)


Day 1Ride through the Valdichiana

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 2Participate in a pasta making demonstration

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 3Explore Rocca d’Orcia

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 4Pedal through Montalcino and the Crete Senesi

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 5Discover the Chianti wine region

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 6End your bike trip in Florence

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


Tuscany cycling map


10 Reviews
Sort By:RatingDate

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