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Tuscany Family Bike Tour

Dates & Prices
Route Rating
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Trip Highlights
  • Iconic hill towns of Montepulciano and Radda in Chianti
  • Family-friendly routes past cypress trees, vineyards, grazing sheep and stone farmhouses
  • Tour a medieval abbey, now a private estate producing its own olive oil and honey
  • Savor classic Tuscan indulgences, including truffles and gelato
  • A night of pizza- and biscotti-making for the kids, and wine tasting and feasting for the adults

Call 800-462-2848, Every day 6am-6pm,PST

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Pedaling & Pizza from Cortona to Chianti

Is this the trip? The one where your kid develops an eye for Etruscan figurative art? Or learns the key features of Quattrocento Renaissance architecture? Maybe not. But it doesn't take a genius to know that Tuscany scores top marks for family fun. Enjoy miles of smiles on kid-approved routes. Discover ancient hill towns and climb a medieval tower (fueled by gelato, of course!). Chianti tasting for the adults. Hands-on pizza making for the youngsters. Enjoy your perfect family adventure in Tuscany.


Day 1 Family-friendly routes past cypress trees, vineyards, grazing sheep and stone farmhouses Savor your first taste of Tuscany at an agriturismo (country retreat and working farm) Enjoy a warm-up spin through the picturesque countryside and quaint towns of the Val di Chiana.

Day 2 Savor classic local delicacies, including truffles, pasta and gelato Visit the famous hilltop town of Montepulciano and wander the medieval streets After lunch at a local café, kids take to a high ropes course, while adults spin their way through the picturesque Montepulciano countryside.

Day 3 Discover iconic hill towns brimming with history  Pedal your way through the Umbrian valleys to the crested town of Castiglione del Lago, with 360-degree views of the surrounding countryside and Lake Trasimeno  The younger set enjoy some free time lakeside while the grown-ups spin along the rolling terrain to Cortona, where Etruscan ruins tell of the city's storied past.

Day 4 Adults taste notable regional wines and dine at a trattoria, while youngsters put together a well-rounded meal - pizza and biscotti! Spin along the Strada dei Castelli (Road of the Castles)  to Radda in Chianti, part of l'Antica Lega del Chianti (The Ancient Chianti League), known today as a major center for Chianti Classico wine production.

Days 5-6 Visit Badia a Coltibuono (Abbey of the Good Harvest), a private estate producing its own olive oil and honey Wonderful vistas abound during a ride through the heart of Chianti Explore ridgetop Castellina, an ancient village with a unique arcaded passageway and hit the shops and gelaterie in town  Visit Greve in Chianti, home to the famous explore Amerigo Vespucci.

Casual Inns

Borgo Tre Rose
Borgo Tre Rose

Valiano (2 nights) Originally a 12th-century residence, this hotel is depicted in a Leonardo da Vinci painting. (pool, tennis)

Relais Villa Baldelli
Relais Villa Baldelli

Cortona (1 night) Once a country villa, this hotel offers spectacular views of Cortona's medieval skyline. (pool)

Relais Fattoria Valle
Relais Fattoria Valle

Panzano (2 nights) Situated just outside the village of Panzano, this former private residence overlooks vineyards and the surrounding valley. (pool)

Guest Reviews About This Trip

One of the best trips we ever had as a family. The kids would have been miserable sightseeing countless museums and churches. What a fabulous way to really experience Italy and the culture while being with a fun social group. My teenagers truly enjoyed having the other kids their age on the trip. We all had a wonderful time. It was great blend of exercise, sightseeing, and cultural experiences. LOVED IT!!!! We had three amazing leaders. All wonderful!!! There will definitely be more Backroads trips in our future!!
Beverly Taavon- Greensboro, NC
Biking Tuscany was a great experience for my family. Our leaders were excellent and catered to our every need. Their knowledge of the region was excellent and they were a constant source of information. In addition, the chemistry between them was very energetic. The choice of lodging and cuisine was superb and offered a great sampling of the area. Thank you, Backroads. We will definitely return.
Diane Artiles- Bethesda, MD
This trip ranks as one of my favorite all-time vacations. The setting in Tuscany is breathtakingly beautiful. This trip was everything I imagined and more! I especially enjoyed meeting the other families. There was also a very nice mix of kids. The trip leaders were exceptional - very personable and took a very special interest in the group. All of them were very good with kids. They provided excellent van support. By the end of the trip, the leaders and the entire group had really bonded. It was really hard to leave such a nice group of people.
Walter Bering- Houston, TX

Trip Dates & Prices

Please click on a date below for specific pricing and possible itinerary variations.

2015 August
2016 May
2016 June
2016 July
2016 August

Don't see your ideal travel date? Call us at 800-462-2848 for Private Trip date availability.

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This Trip Is Rated Level 1-4

Routes For All Abilities
Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. We know your pace may vary from one day to the next-and your traveling companion's may differ somewhat from yours. So we present a range of mileage options, and each day you decide exactly what and how much you want to do.

Daily Route Options
Level 1 Level 2 Level 3 Level 4 Level 5
miles feet gain miles feet gain miles feet gain miles feet gain miles feet gain
1 15* 100 24 600
2 13* 1000 24* 1300 41 1900
Kids: High Ropes Course & Rock Climbing Activity
3 12* 200 30 400 44 800
Kids: Activities at Lake Trasimeno
4 17 1300 24* 1800 32 2400
Kids: Pizza and Biscotti Making at Agriturismo La Quercia
5 18* 1600 45 3100
24* 1800
6 8 700

On this Family Trip, liberal van shuttling is incorporated into the itinerary to facilitate our activities and mileage is kept moderate to enable you to spend more time exploring on your own.

* Includes a shuttle

Private Trips Options & Pricing

Gather your favorite people to share a Backroads adventure on a ready-to-book Private Trip - featuring all the legendary Backroads hallmarks from expert leaders to unforgettable activities.

You can pick from a large selection of dates for your group of 8 or more. Call us for date availability.

If your party has fewer than 8 guests, or if your preferred date is not available, we'll create a departure just for you.

Pricing for Private Trips (prices may vary based on departure date)


2 - 3 guests from $6,098 pp dbl. occ. 8 - 9 guests from $4,298 pp dbl. occ.
4 - 5 guests from $5,098 pp dbl. occ. 10 - 11 guests from $3,698 pp dbl. occ.
6 - 7 guests from $4,598 pp dbl. occ. 12 or more guests from $3,398 pp dbl. occ.


2 - 3 guests from $6,098 pp dbl. occ. 8 - 9 guests from $4,298 pp dbl. occ.
4 - 5 guests from $5,098 pp dbl. occ. 10 - 11 guests from $3,698 pp dbl. occ.
6 - 7 guests from $4,598 pp dbl. occ. 12 or more guests from $3,398 pp dbl. occ.

Please note: Youth savings do not apply to Private Trips.

For 36 years, Backroads has been perfecting the art of active travel. We are the Tuscany tour experts. See our award-winning Europe Italy biking tours, Europe Italy walking and hiking tours and Europe Italy multisport tours.


Casual Inns

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Route Rating

arrow Level 1-4


Arezzo, Italy/Florence, Italy

Detailed Itinerary

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Trip Notes

All meals included except 2 lunches, 1 dinner

Recommended Ages

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Recommended Reads

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