1.888.883.7948 [email protected]
1.888.883.7948 [email protected]

Tuscany Family Bike Tour

(3 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


Discover the best of Tuscany on your own two wheels. Whether it’s great food, local wines, a scenic ride over the Crete Senesi or an easy spin through the Val di Chiana, Tuscany has got it all. Join DIGnGO on a family bike tour in Tour in Tuscany that includes great activities for kids, wine tastings with local wine makers for grown-ups and everything else you’ve ever hoped for.


  • 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 17 - May 22, 2020
  • May 24 - May 29, 2020
  • May 31 - Jun 5, 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
  • 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 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

Day 2

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

Day 3

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

Day 4

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

Day 5

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

Day 6

Your family cycling vacation in Tuscany ends at the Chiusi Chianciano Terme train station.


Villa Curina

Castelnuovo (2 nights)

SI Montalcino

Montalcino (1 night)

Albergo Duomo

Montepulciano (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


Bike tour of Tuscany map


3 Reviews
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Vicki S.

Family Traveller

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!

August 1, 2018

Joe D.

Family Traveller

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.

July 26, 2018

Mark H.

Family Traveller

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.

April 27, 2017