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1.888.883.7948 [email protected]

Tuscany Family Bike Tour

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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.


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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

The fun starts when we all meet in Florence. Everyone transfer from there to Castellina in Chianti, where you have a light lunch to kick things off! The municipality itself has just 2,800 people, and is very historic in its nature. For example, you will get a glimpse of many structures from ages before our time, such as the huge Castle Rocca.

The unique thing about this massive place is that it has a museum inside of it for those who are interested in its rich past to explore. This enormous 14th Century tower is a must see. The Church of San Salvatore is also a famous curiosity among visitors, being that they have beforehand heard about the fresco of Madonna with Child from around that same time frame (the Church is just a little younger, a 15th Century piece of architecture), along with the wooden Statue of Christ that is just as ancient in age.

Next you all casually bike to the Villa Curina, your hotel for the next two nights, a little sixteenth century village full of history and fascination.

Dinner is served at a local restaurant.

Today’s Ride: 23 miles with 1,600 feet of climbing

Day 2

Today 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

After a break in the heart of town, cruise your way back to the Villa Curina.

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: 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

Following a delightful breakfast venture to the heart of Tuscany and toward the town of Asciano.

In the afternoon keep ridding toward your next destination while the little ones head to Saltalbero Adventure Park. It is a location that they will never get enough of! Let’s hope they love zip lines, because this park is packed with them on the fun courses. From many different heights off the ground, there are acrobatic sequences that are installed in the trees, rock walls, and poles that will have you and yours playing for hours.

After all that fun and excitement, you are starting feel the hunger coming on. Dinner is held at a wonderful restaurant nearby.

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

Today, you pedal through the beautiful terrain of Crete Senese. This Italian region of Tuscany sports lots of hills and woods, and many describe the color of the sand as giving the entire landscape a feel that is almost lunar. The sediments of Pliocene Sea shape the sand has a characteristic known as mattaione. The sea itself covered the land over 2.5 million years ago, and the dry Accona Desert is very close by.

After taking a break in a mediaeval village, you keep cycling before arriving at your home for the next two nights, the Albergo Duomo. The cosy rooms, situated in an old Renaissance Palazzo, let you relax.

Dinner is at an authentic trattoria.

Today’s Ride: 33 miles with 3,800 feet of climbing
Short Option: 18 miles with 2,000 feet of climbing

Day 5

Your fifth day in glorious Tuscany starts with a simple, but delicious breakfast before you prepare to bike your way from Albergo Duomo 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, take some time to rest 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, the kids participate in an authentic cooking class, while you 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!

Your farewell dinner is served in town.

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

Enjoy breakfast at the hotel Albergo Duomo 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 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