NEW!
Family Breakaway
Big adventures for families with older teens & 20-somethings
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Tuscany Family Breakaway Bike Tour New!

Overview
Lodging
Reviews
Dates & Prices
Route Rating
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Trip Highlights
  • Ride, relax and savor every drop of this vintage Backroads experience 
  • Pedal our favorite Tuscan roads with ample shuttle support
  • Luxuriate at handpicked hotels that represent Tuscany's finest
  • Taste regional specialties like pecorino cheese and olive oil
  • Discover idyllic hilltop towns brimming with medieval and Renaissance architecture

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

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Chianti to Montalcino, the Birthplace of Brunello

Few things in this world live up to the hype. But everything you've ever heard about Tuscany is true. It's not a destination. It's a sublime experience. Routes lined with cypress trees overlooking the patchwork vineyards below will stop you on your bike. And no view will compare to that view. Until you round the next bend and see another. It's a wonder anyone ever finishes the rides. And that's only what you'll see; imagine all the flavors and luxuries you'll discover.

Day 1 The quintessential Tuscan journey, offering the most scenic routes from Florence to Montalcino  Sample fresh Tuscan specialties at an agriturismo before biking serene roads past olive orchards, farmhouses and wheat fields  Pedal to medieval Greve in Chianti, where you can stroll through the narrow lanes and pretty piazza of this former market town before continuing to the splendid Castello del Nero.

Days 2-3 Ascend quiet roads into the heart of the Chianti region The hidden nooks of Via delle Volte, Castellina's unique arcaded passageway, are a delight to explore  Cruise the ridge to the ancient hilltop town of Radda, long the center of Chianti wine production Visit Badia a Coltibuono ("Abbey of the Good Harvest"), where you're treated to a private tour and olive oil tasting  Stroll Siena's medieval streets in search of the perfect trattoria for dinner.

Day 4 Visit Monte Oliveto Maggiore, a Benedictine abbey featuring some of the best preserved frescoes in Europe  Our route leads through the chalk hills of the Crete Senesi, often depicted in 14th- and 15th-century Florentine paintings Dine in style at San Felice's renowned restaurant.

Days 5-6 The narrow streets of Montalcino are yours to discover  Point your wheels toward southern Tuscany, where stately cypresses crisscross open rolling hills  Pedal through the undulating wheat fields and hilltop towns of the Val d'Orcia  In Pienza, marvel at extraordinary Renaissance architecture and sample splendid pecorino cheese  Visit the imposing abbey of Sant'Antimo, where monks celebrate mass with stirring Gregorian chants.

Premiere Inns

Castello del Nero
Castello del Nero

Tavarnelle Val di Pesa (2 nights) A castle steeped in Tuscan charm and situated on a hilltop overlooking rolling vineyards and olive orchards in the Colli Fiorentini. (pool, spa)

Relais Borgo San Felice
Relais Borgo San Felice

San Felice (2 nights) This luxury property produces its own wine, and is praised by the Hideaway Report as an “enchanting resort enclave set within a restored medieval hamlet fringed by olive groves and vineyards in the Chianti Classico region.” A Relais & Châteaux member. (pool, spa, tennis)

Castello di Velona
Castello di Velona

Castelnuovo dell'Abate (1 night) Superb hilltop views await at this elegant 11th-century fortress featuring terra-cotta floors, individually decorated rooms and a magnificent vantage point above the Val d’Orcia. A Small Luxury Hotels of the World member. (pool, spa)

Guest Reviews About This Trip

Tuscany is synonymous with ageless scenery, fascinating history and delectable cuisine. And an ideal way to experience it is by bike with Backroads. You'll enjoy rich and authentic experiences that are a result of years of research and cultivated relationships. We look forward to introducing your whole family to the wonderful places and welcoming people that make this region so special.
Carlos Martinez Abad - Regional Coordinator, Italy

Trip Dates & Prices

For dates and prices, please give us a call at 800-462-2848, daily 6 a.m. - 6 p.m., Pacific time. Or chat online,
e-mail us or schedule a call.

This Trip Is Rated Level 2-5

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
Day EASYGOING ACTIVE AVID
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 22 1400
2 25* 1700 38* 2200 48 2900 55 3300
3 20* 1900 31 2500 38 3200 48 3900
4 28* 1200 33* 1200 49 2600 61 3500
5 22* 2000 32* 2400 45 3500 62 4700
6 14 900
 
note:

* Includes a shuttle

Private Trips Options & Pricing

Gather your favorite people to share a Backroads adventure on a Custom Trip - featuring all the legendary Backroads hallmarks from expert leaders to unforgettable activities. Please call for date availability and pricing.

For 35 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.

Trip Notes

All meals included except 2 lunches, 1 dinner

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