Backroads Tuscany Family Bike Tour
Tuscany, Italy
Backroads Tuscany Family Bike Tours
Tuscany, Italy
Backroads Tuscany Bike Tour
Tuscany bike tours
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Tuscany Bike Tour - For Families with Teens & Kids

Cortona to Chianti: Tuscan & Umbrian Countryside

Best for ages 9+ (Ages 4+ ok) | Min. age to ride own bike: 9+ | Min. age to ride e-bike: 16+

Family — Teens & Kids

6 days 5 nights

Activity Level: 1-4

Casual Hotels

From: $3,999 - $4,099 pp dbl occ

($750 for sgl occ)

Tuscany scores top marks for family fun. Enjoy miles of smiles on kid-approved routes. Discover ancient hill towns (fueled by gelato, of course!). Wine tasting for the adults. Hands-on pizza making for the youngsters. Fun for everyone. Your perfect family adventure... in Toscana!

Italy Tuscany Family Bike Tour map
Italy Tuscany Family Bike Tour map


Start Arezzo / End Florence

Start/End locations may vary. Do not book flights until your trip details are confirmed.


  • Bike and play in the family-friendly, postcard-perfect Tuscan hill towns of Cortona and Radda in Chianti
  • Cruise by bike on peaceful roads through lush colorful fields of sunflowers, corn, sugar beets and tomatoes
  • Adventure across Umbria's Lake Trasimeno or up through the trees on a rope course park (just for kids)
  • Taste exceptional Tuscan wines, dine at authentic trattorias and pair up with the kids to learn the art of pizza-making


Accommodations may vary based on departure date.
6 Days Casual Hotels
Accommodations may vary based on departure.
Days 1-3

Bike through the picturesque countryside of the Val di Chiana past cypress trees, sunflower fields, grazing sheep and farmhouses | Savor farm-fresh products over a family lunch | Ride to the hilltop town of Montepulciano while kids take to a high ropes course | Follow cycling routes to the town of Castiglione del Lago, with views of an iconic Umbrian landscape and Lake Trasimeno | Kids have fun with water sports while the grown-ups bike rolling terrain back to Tuscany | Step back in time as you stroll the historic streets of Cortona | In the evenings, have your fill of pasta, kid-friendly contorni and—for the adults—wines | Longue poolside at our hotel, a former medieval village, the ideal place for rest and play.

Exterior view of Borgo Tre Rose
Borgo Tre Rose
| Casual Hotel

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

Days 4-6

Ride along the Strada dei Castelli (Road of the Castles) to Radda in Chianti, known today as a major center for Chianti Classico wine production | Young artists try their hands at painting their own ceramic souvenirs in a fun art class | A memorable family dinner experience awaits as budding kid chefs put together a well-rounded meal—pizza! | Ride scenic routes through Chianti's inviting hills | Shop for hand-painted souvenirs and admire Renaissance-style designs at Ceramiche Rampini | Visit Badia a Coltibuono (Abbey of the Good Harvest) and taste the honey produced on-site | Wonderful vistas abound during a ride through the heart of Chianti | Pause to enjoy delicious gelato in ancient towns | Celebrate a Tuscan family vacation with a meal amid the olive groves at our charming hotel.

Pool view of L'Ultimo Mulino
L'Ultimo Mulino
Gaiole in Chianti
| Casual Hotel

Travel back in time at this country hotel, housed in an antique mill dating from the 15th century. (pool)

Looks like you’re traveling with a smaller group

Our Private Trips are best for groups of 6 or more. We suggest joining a scheduled trip.

Please Select a Group Size

Group size is required to show per-person pricing. Your group size can be approximate and can change.

Activity Level: 1-4

Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. Several routes and a range of levels are offered each day so you can choose how much or how little activity you want to do. Learn more about how we determine activity levels.

Route notes

This region is known for its rolling terrain and hilltop towns. We'll flatten some of the hills by incorporting liberal van shuttling into the itinerary, and the mileage is moderate to enable you to spend more time exploring on your own. Most routes we follow are paved, though on occasion there are some rough sections.

Daily Route Options

* Includes shuttle.
Day 1
Level 1 | 11 miles* | 500 ft. gain
Level 2 | 20 miles | 1200 ft. gain
Day 2
Level 1 | 11 miles* | 600 ft. gain
Level 2 | 24 miles* | 1200 ft. gain
Level 3 | 34 miles | 1400 ft. gain
Level 4 | 40 miles | 2500 ft. gain
Just For Kids
High Ropes Course & Rock Climbing Activity (2 hours) | min. age: 6+
Day 3
Level 1 | 15 miles* | 800 ft. gain
Level 2 | 27 miles | 1300 ft. gain
Level 3 | 36 miles* | 1700 ft. gain
Just For Kids
Activities at Lake Trasimeno (2 hours) | min. age: 6+
Day 4
Level 1 | 15 miles* | 1000 ft. gain
Level 2 | 17 miles* | 1600 ft. gain
Level 3 | 29 miles | 2400 ft. gain
Level 4 | 36 miles | 3400 ft. gain
Just For Kids
Ceramics Painting (2 hours)
Day 5
Level 1 | 11 miles* | 800 ft. gain
Level 2 | 15 miles* | 1700 ft. gain
Level 3 | 21 miles* | 2300 ft. gain
Level 4 | 36 miles | 3500 ft. gain
Tour & Honey Tasting at Badia A Coltibuono (1 hour)
Day 6
Level 1 | 6 miles* | 700 ft. gain
Level 2 | 15 miles | 1500 ft. gain

What's Included

Available Bike Options

The key to a stellar day's ride is a bike that's perfectly in tune with your cycling style… Backroads has you covered with the best bike fleet in the world! Please note that bike requests are subject to availability and prioritized based on the date they're submitted.

Click the arrow to see all bike options.

Backroads Performance Road Bike
Backroads Performance Road Bike
Performance Road Bike

Included in your trip price

This custom-designed titanium bike is lightweight and responsive, featuring Shimano Ultegra Di2 electronic shifting, 11-speed compact gearing, a premium Mavic Ksyrium Pro wheelset and a full carbon fork. 

Backroads Touring Bike
Backroads Touring Bike
Touring Bike

Included in your trip price

A proven classic, this custom-designed titanium bike is suited for a wide range of cyclists. It features a comfortable ergonomic seat and a long wheel base that add to the bike’s control and stability.

Backroads Electric-Assist Bike
Backroads Electric-Assist Bike
Electric-Assist Bike

Included in your trip price

Keep pace or zip ahead, pedaling with an electric boost. This bike provides plenty of power to flatten the hills and more than enough battery range to cover the distance.
Min. age to ride e-bike: 16+

Cannondale Synapse Pro Carbon Bike
Cannondale Synapse Pro Carbon Bike
Carbon Bike

Ride like a pro with the top-of-the-line carbon Cannondale Synapse Hi-Mod Red ETAP AXS. Delivering phenomenal acceleration and handling in a light and powerful package.
$650 rental fee; subject to availability

Co-Motion Torpedo Tandem Bike
Co-Motion Torpedo Tandem Bike
Tandem Bike

This hand-built frame features Co-Motion's custom-designed cro-moly steel tubeset, powerful Avid disc brakes, Shimano Ultegra drive train, and a custom, upgraded wheelset. For experienced tandem riders.
$400 rental fee

Child's Bike
Child's Bike
Kids' Bikes

Included in your trip price

Backroads is the only travel company to manufacture its own line of kid's bikes. While the wheels might be small, the performance is big—it's the perfect choice for kids. On our Family Trips, you'll find 20" and 24" bikes.

Burley Kazoo Trailer Bike
Burley Kazoo Trailer Bike
Trailer Bike

Included in your trip price

The Burley Kazoo trailer bike, for children up to 85 pounds, attaches to an adult bike with your child providing some of the pedal power for a real team effort! It's ideal for kids who aren't yet ready for bike touring. 

Also Included

  • All breakfasts, 4 dinners, 4 lunches
  • Expertise and services of our experienced Trip Leaders
  • Snacks and beverages between meals
  • Additional guides and experts from the region on many trips
  • Van shuttles to support a variety of route options
  • Comprehensive Travel Planner with detailed pre-trip information
  • Private guided tours at museums, historic sites, wineries and other select attractions as noted in the Travel Planner
  • All gratuities at hotels and restaurants
  • Special events, including wine tastings and other select attractions as mentioned in the Travel Planner
  • On biking and multi-adventure trips, use of fully equipped Backroads titanium bike plus helmet and accessories
  • Trailercycles, carriers, and kid-sized helmets for Family Trips
  • Equipment and experienced guides for kayaking, rafting, snorkeling, sailing and canoeing as described
  • Park and other entry fees
  • Fares for trains, ferries and other modes of travel as listed in the Travel Planner
  • Select coach transfers
  • Baggage transfers and porterage

Ask a trip expert

Have a question and need expert advice? Our team of Trip Consultants is here to help! You can also visit our Help Center.

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