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

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Trip Highlights
  • A quintessential Tuscan experience from south to north
  • Relax at day's end in cozy historic hotels, all with swimming pools
  • Explore some of the region's most celebrated towns, including Pienza, Montalcino, Siena and Radda in Chianti
  • Sample classic Tuscan indulgences, such as truffles and gelato
  • Pedal rolling hills past Brunello, Chianti Classico and Sangiovese vineyards

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

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A Taste of Tuscany from Pienza to Siena & Chianti

To D.H. Lawrence, Tuscany was "the perfect centre of man's universe." Poet Shelley called the region a "paradise for exiles." Dante, a Tuscan native, more than likely called it "divine." You and your family will undoubtedly conjure up a few superlatives of your own as you pedal from one unbelievable view to the next, gaze in awe at incredible Renaissance art and architecture, and savor delicious pecorino cheese, homemade pasta, fruity olive oils and celebrated Chianti and Brunello di Montalcino wines. Few things in this world live up to the hype. We're delighted to report that everything you've ever heard about Tuscany is true.

Days 1-2 Explore some of the region's most celebrated towns, including Pienza, famous for pecorino cheese, exquisite ceramics and Renaissance architecture After savoring Tuscan treats, pedal cypress-lined roads through southern Tuscany's open undulating terrain into the Val d'Orcia   Montepulciano, with its winding streets and hidden squares, invites a stroll.

Day 3 Climb through a sea of vineyards to the wine village of Montalcino,  where enoteche pour samples and remarkable views reach as far as Siena on a clear day  Check out Abbazia di Monte Oliveto Maggiore, an active monastery offering sublime countryside vistas, where monks still pray in Gregorian chant.

Day 4 Engaging Q&A session with Dario Castagno, author of Too Much Tuscan Sun  Bike past the exposed chalk hills of the Crete Senesi, often depicted in 14th- and 15th-century Florentine and Sienese paintings  Sun-baked pastures dotted with sheep and crumbling stone farmhouses make way for oak woodland and olive groves Explore Siena's charming labyrinth of pedestrian streets and linger in the fashionable Piazza del Campo by night for the best people watching in Italy!

Days 5-6 Pedal rolling hills alongside Chianti Classico and Sangiovese vineyards  Get to know ridgetop Radda, the center of Chianti wine production, and Gaiole in Chianti, also part of the Antica Lega del Chianti and a friendly rival to neighboring Radda  Looking for a gift? Family-owned Ceramiche Rampini offers ceramics hand-painted in the Renaissance tradition.

Guests Reviews About This Trip

In the nearly two decades I've been with Backroads, I've had the privilege to research and design numerous Tuscany itineraries as the popularity of active travel in this region has soared. Nothing would make me happier than to share my favorite local connections with you on this special Breakaway edition. You'll enjoy rich, genuine experiences that are a result of years of research and cultivated relationships. Join us for a taste of Tuscany's very best!
Jeff Cantarutti - Regional Manager, Tuscany

Casual Inns

Albergo le Terme
Albergo le Terme

Bagno Vignoni (2 nights) This charming family-owned hotel overlooks the town's central piazza, whose ancient pool is fed by underground thermal springs. (pool, spa)

Borgo Casabianca
Borgo Casabianca

Asciano (1 night) A warm welcome awaits at this agricultural estate standing on a high ridge between the Chiana Valley and the famed Crete Senesi. (pool, tennis)

Villa Curina Resort
Villa Curina Resort

Curina (2 nights) A tranquil 16th-century villa with wooded grounds, an Italian-style garden and a small church with frescoes by Arcangelo Salimbeni. (pool, tennis)

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.

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 17 1400
2 25* 1600 34 1700 44 2500 65 4300
3 22* 1600 42 3000 59 4400
51 3900
4 31* 1300 39 1700 52 2500
5 21* 1900 53 3400 64 4800
6 13 700

* Includes a shuttle

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.


Casual Inns

6 days, 5 nights
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Trip Price**
  • $3,798 pp dbl. occ.
  • (+$680 for sgl. occ.)

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Florence, Italy

Detailed Itinerary

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Dates & Prices

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2014 Family Breakaway Dates
Trip Notes

All meals included except 2 lunches, 1 dinner

Recommended Reads

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Cancellation Policy

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** Prices may change. Once you book your trip, your price is guaranteed.