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

Dates & Prices
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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  Kick off the week with superb Michelin-starred cuisine inspired by Tuscan traditions and flavors.

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  Dine in style at San Felice's renowned restaurant.

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  Stroll Montalcino's medieval streets in search of the perfect trattoria for dinner.

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) Described 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) Soak up superb hilltop views at this elegant 11th-century fortress featuring 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

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

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 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
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 19 1300
2 24* 1800 40* 2200 48 3100
3 19* 1800 29 2400 36 3100
46 3900
4 28* 1200 33* 1200 48 2700
5 22* 2000 32* 2400 45 3500 62 4400
6 14 900

* 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 $6,998 pp dbl. occ. 8 - 9 guests from $5,498 pp dbl. occ.
4 - 5 guests from $6,198 pp dbl. occ. 10 - 11 guests from $4,898 pp dbl. occ.
6 - 7 guests from $5,698 pp dbl. occ. 12 or more guests from $4,598 pp dbl. occ.

All Private Singles-Solos trips require a minimum of 16 guests.

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.


Premiere Inns

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Route Rating

arrow Level 2-5


Florence, Italy

Detailed Itinerary

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Trip Notes

All meals included except 2 lunches, 1 dinner

Recommended Reads

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