Tuscany Family Bike Tour
Backroads Tuscany Family Breakaway Bike Tour
Backroads Tuscany Family Breakaway Bike Tour
Backroads Tuscany Family Breakaway Bike Tour
Backroads Tuscany Family Breakaway Bike Tour
Backroads Van in Tuscany
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Tuscany Family Bike Tour - Older Teens & 20s

A Taste of Italy from Pienza to Siena & Chianti

Ride from one unbelievable view to the next. Marvel at extraordinary Renaissance art and architecture. And taste delicious pecorino cheese, homemade pasta, fruity olive oils and tiramisu. Few things in this world live up to the hype. We're happy to report that everything your family has heard about Tuscany is true.

THIS ITINERARY: 6 days, 5 nights

ACCOMMODATIONS: Casual Plus Hotels

FROM: $3,799 pp dbl occ
($500 for sgl occ)

Special Kids Prices


Start Arezzo / End Florence

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

  • Experience a quintessential Tuscan vacation, biking from south to north through a beautiful rolling landscape
  • Savor delectable gelato and enjoy family dinners of handmade pastas, bruschetta and other local specialties
  • Explore some of the region's most celebrated towns, including Pienza, Montalcino, Siena and Radda in Chianti
  • Bike tranquil roads and lush green hills past picturesque Brunello, Chianti Classico and Sangiovese vineyards
The Backroads Experience
The Backroads Experience
Backroads Biking Trips
Meet Our Leaders
Accommodations may vary based on departure date.
6 Days Casual Plus Hotels
Accommodations may vary based on departure.
Days 1-2

Experience some of Tuscany's must-see highlights, including Pienza, a World Heritage site famous for exquisite ceramics, pecorino cheese and Renaissance architecture | Regional specialties provide the perfect fuel for rides on cypress-lined roads | Bike through southern Tuscany's rolling terrain into the Val d'Orcia | Take a family stroll on the winding streets of Montepulciano, pausing for an aperitivo or gelato on one of its hidden squares | Idle poolside at our welcoming hotel.

Albergo Le Terme
Albergo le Terme
Bagno Vignoni
| Casual Plus Hotel

This enchanting family-owned hotel overlooks the town's central piazza, whose ancient pool is fed by underground thermal springs. (pool, spa) 

Day 3

A sea of vineyards lines our bike route to Montalcino, a wine village where enoteche pour samples and—on a clear day—remarkable views reach as far as Siena | Visit Abbazia di Monte Oliveto Maggiore, the region's most notable monastery, where monks still pray in Gregorian chant | Read or relax and simply take in the scene from our hotel's lovely terrace.

Borgo Casabianca
Borgo Casabianca
| Casual Plus Hotel

An agricultural estate standing on a high ridge between the Chiana Valley and the famed Crete Senesi. (pool)

Days 4-6

Join a renowned local author for a fascinating Q&A session | Ride past the sun-drenched chalk hills of the Crete Senesi, often depicted in 14th- and 15th-century Sienese and Florentine paintings | Sheep-dotted pastures and crumbling stone farmhouses lead to olive groves and oak woodland | Explore magnificent Siena with your family | Bike rolling hills alongside legendary Chianti Classico and Sangiovese vineyards | Discover ridgetop Radda, the center of Chianti wine production | Up for more mileage? Ride to Castellina, a medieval village with a unique arcaded passageway | Shop for souvenirs at family-owned Ceramiche Rampini, offering ceramics hand-painted in the Renaissance tradition.

Villa Curina Resort
Villa Curina Resort
| Casual Plus Hotel

A tranquil 16th-century villa with wooded grounds, an Italian-style garden and a small church with frescoes by Arcangelo Salimbeni. (pool)

Dates & Prices

The earlier you book, the more choice you'll have and the lower your price. And you can always change your mind — you won't be charged to transfer to a different trip before your final payment is due. View cancellation policy

Click on dates for pricing, itinerary variations and to book your trip. Price is per person, double occupancy.

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Activity Level: 2-5

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. LEARN MORE.

Day 1
Level 2 | 23 miles | 1200 ft. gain
Day 2
Level 2 | 18 miles* | 1500 ft. gain
Level 3 | 34 miles | 2500 ft. gain
Level 4 | 47 miles | 3800 ft. gain
Level 5 | 65 miles | 5700 ft. gain
Day 3
Level 2 | 14 miles* | 1900 ft. gain
Level 3 | 27 miles* | 2600 ft. gain
Level 3 | 37 miles* | 3800 ft. gain
Level 4 | 42 miles | 4200 ft. gain
Level 5 | 51 miles | 5300 ft. gain
Day 4
Level 2 | 26 miles* | 1900 ft. gain
Level 3 | 30 miles | 2100 ft. gain
Level 4 | 42 miles | 3200 ft. gain
Level 5 | 49 miles | 3800 ft. gain
Day 5
Level 2 | 18 miles* | 2000 ft. gain
Level 3 | 30 miles* | 3700 ft. gain
Level 4 | 49 miles | 4200 ft. gain
Level 5 | 57 miles | 5500 ft. gain
Day 6
Level 2 | 13 miles | 1200 ft. gain
* Includes shuttle.

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! Read on for your available bike options for this trip.

Performance Road Bike

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. 

Touring Bike

A proven classic, our most popular 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.

NEW! Electric-Assist Bike

Our newly redesigned titanium e-bike is a lightweight yet powerful machine unique in the world of e-bikes. It provides plenty of power to flatten the hills and more than enough battery range to cover the distance.

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—it’s built for hard-core riders.
$400 rental fee

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

Also Included

  • All breakfasts, 4 lunches, 4 dinners
  • 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 FAQ's.

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