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Home / Europe / Italy / Tuscany Family Bike Tour

Tuscany Family Bike Tour

(3 Reviews)
  • 6 days / 5 nights
  • Luxury hotels
  • Small groups

Discover Tuscany on your own two wheels, and have fun together as a family. Our family bike tour takes you on kids-friendly route through Tuscany. Whether you’re cycling through endless vineyards, riding amid olive trees, discovering ancient hill towns, learning how to make pizza, or tasting some wonderful wines, biking in Tuscany with DIGnGO is a perfect cycling adventure.


DAYS 1-2

Welcome to fabulous Tuscany. | Start your journey through Toscana with a visit to picturesque Castellina in Chianti, a medieval village with a unique covered walkway that goes around the city. | Ride through the beautiful Chianti area, where vineyards, chestnut forests, picturesque villages, and charming castles flank quiet roads. | Settle into the beautiful hotel, Villa Curina, immersed in the peaceful countryside. | End the day with a wonderful dinner at a local restaurant. | Set off from our hotel on your bicycle to ride scenic roads en route to the capital of Chianti Classico, Radda in Chianti. | Bike along the dense vineyards of the Chianti and stop to enjoy a self-guided visit of a local shop producing handmade and hand painted pottery in the Italian artisan tradition. | On foot, discover Siena, the medieval city known worldwide for the Palio di Siena, Italy’s most important horse race. | Stroll the high-end boutiques and shops before eating local delicacies at a local restaurant in town.

Villa Curina Resort
Castelnuovo | 4-star hotel

Set among the rolling hills and olive groves of the Tuscan countryside, surrounded by the vineyards of Chianti, and just a few miles from the historic town of Siena, the Hotel Villa Curina dates back to 16th-century.


Take in a beautiful countryside sunrise as you enjoy a delicious breakfast on the terrace of your hotel. | Kids set out on an exciting ropes course at the Saltalbero Adventure Park. | Cycle through a rolling hills dotted landscape to the town of Asciano—the centre of Crete Senesi—and explore the Romanesque collegiate church of St Agata. | Savor the sights of the Crete Senesi, an area often described as a « lunar landscape ». | If you dare, take on the challenging climb of Montalcino, home to one of Italy’s most famous and prestigious wine, the Brunello di Montalcino.

Hotel Si Montalcino
Montalcino | 3-star hotel

Looking towards San Quiro D’orcia, Castiglione D’orcia and Bagno vignioni, the hotel is just 1 km from the walls of Montalcino and the Brunello vineyards. From the terrace, the hotel offers a view on the valley below Mount Amiata.

DAYS 4-6

Venture by bicycle to the tiny hilltop village of Rocca d’Orcia, and the fortress of Rocca di Tentennano standing on a pinnacle high above the valley. | On the way, admire the views of Mount Amiata, Tuscany’s highest peak. | An exhilarating downhill ride brings you to the heart of the Val d’Orcia. | Pedal through Monticchiello, an ancient village situated at the foot of an uphill stretch that is world famous for its beautiful cypress trees. | Arrive in Valdichiana, a region with endless vineyards and olive orchard. | Wander in the town of Montepulciano and try local specialties at a wonderful trattoria. | Pedal past the hilltop towns of Petroi and Castelmuzio. | Wander the grounds of the monastery of Sant’Anna in Camprena, where scenes of the Oscar-winning film The English Patient were filmed. | Explore the medieval town of Pienza, known for its amazing UNESCO Historic Centre. | Take in unparalleled views of Valdichiana. | Kids get a lesson in pizza making at a family-owned restaurant. | Stroll the streets of Montepulciano, home to the Santa Maria Assunta Cathedral. | Celebrate your final evening with a wonderful dining experience.

Albergo Duomo
Montepulciano | 3-star hotel

This is a family run hotel situated in an old Renaissance palace just 30 meters from the old center of Montalcino, the Piazza Grande.



See our booking form section on this page for all departure dates.

Get together with your traveling companions and share a great DIGnGO adventure. You can take over any of our guided tours and make it your own private cycling tour. If your departure date is not available, we’ll set a date for you, your family, and friends. Call us at 888-883-7948 to start planning your trip.

We’ll make it happen! Tell us what your ideal cycling experience would be and we’ll work closely with you to put it together. Our travel agents will arrange a bike trip that fits your needs, interests, schedule and budget. Call us at 888-883-7948 to speak with a custom tour manager.

What's Included


  • All breakfasts, 1 lunch and 4 dinners
  • Multiple daily routes
  • A fully equipped bicycle
  • Garmin GPS with directions
  • Handlebar bag, helmet & water bottle
  • 1 leader for every 3 guests
  • Snack & drinks during the day
  • Gratuities at hotels and restaurants
  • Guided tours, tastings & 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 start/end
  • Pre or post trip lodging
  • Minibar, massages, etc
  • Alcoholic beverages
  • Gratuities for your Leaders


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

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