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

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Trip Highlights
  • Soak up the medieval flavor and ancient traditions of charming hilltop towns
  • Enjoy gracious hotels with distinct local flavor
  • Taste splendid wines like Sagrantino, Montefalco Rosso and Vino Nobile di Montepulciano
  • Delight in the area's specialties: hearty ribollita, panzanella, fresh pastas and delicious pastries
  • Get to know our favorite friends and colorful local people

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

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Undiscovered Umbria to Cortona, Land of the Tuscan Sun

No doubt you'll arrive with certain expectations. After all, artists and writers have sung the praises of Tuscany and Umbria for centuries. But somehow it's still a surprise, the sensory feast that surrounds you. You're still floored by the beauty of silvery olive groves and endless acres of vineyards. By the slow pace of life. By the symphony of flavors in traditional dishes passed down through generations. By the chefs and vintners who are proud to share their talents. And the sheer passione of the locals. Expectations exceeded? Just another day in the heart of Italy.


Days 1-2 Medieval flavor and ancient traditions await in charming hilltop towns  The only hill town on the valley floor, Montefalco is a great spot for soaking up views of Assisi to the north and Spoleto in the south  Coast downhill to a bountiful picnic lunch in the heart of the Sagrantino wine (Umbria's "big red") production zone Dine and wander in timeless Bevagna, perhaps pausing to browse for ceramics and silver Taste splendid wines, like Sagrantino, Montefalco Rosso and Vino Nobile di Montepulciano  Beauty abounds in Assisi, from the stunning Basilica of Saint Francis to the verdant valley below.

Day 3 Imagine you're in a postcard as you pedal along a winding road flanked by bright red poppies, cypress trees and undulating hills  Spin through the Umbrian countryside, where fortified towns and distant Mount Subasio provide a dramatic backdrop  We're treated like royalty at the luxurious Borgo dei Conti Resort, a Relais & Châteaux fortress-turned-castle dating back to the 13th century.

Days 4-6 Welcome to Tuscany!  Cruise past olive groves and sunflower fields to La Braccesca wine estate for an exclusive cooking demo and lunch  Pedal through the Chiana Valley, where white Chianina cows graze Bike to historic hilltop Cortona, surrounded by 3,000-year-old Etruscan walls, and the setting for Under the Tuscan Sun Taste splendid wines, like Sagrantino, Montefalco Rosso and Vino Nobile di Montepulciano Giovanni, our longtime local guide, leads us through this celebrated town  Savor a classic Tuscan landscape during an easy ride past ancient farmhouses, vast wheat fields and cypress-lined roads.

Premiere Inns

Relais Villa Zuccari
Relais Villa Zuccari

San Luca (2 nights) In the Zuccari family since the 1500s, this gorgeous villa is surrounded by expansive rose-filled gardens and the vineyards of Montefalco. (pool)

Borgo dei Conti
Borgo dei Conti

Perugia (1 night) Once a medieval fortress, this luxurious château is set among manicured gardens and nestled in the Umbrian countryside. A Relais & Châteaux member. (pool, spa, tennis)

La Corte dei Papi
La Corte dei Papi

Cortona (2 nights) A superbly appointed 18th-century country house, rated one of the top hotels in Italy. (pool)

Guest Reviews About This Trip

This trip introduces you to two fantastic regions: Umbria and Tuscany. While dramatically less traveled than Tuscany, Umbria offers many if not all of Tuscany's famed physical and cultural qualities. In both areas, you'll experience charming hill towns that have maintained their medieval flavor and ancient customs. You'll witness classic tableaus of rolling fields, vineyards, olive groves, old farmhouses, cypress-lined roads and nonne (grandmothers) strolling arm-in-arm. And you'll enjoy some of the most pleasant biking in the Backroads lineup of worldwide trips, with shuttles to help you up the bigger hills.
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 1-4

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 19 200 26 900
2 26* 600 41* 700
50 800
3 29* 2800 44 4400
57 5300
4 26* 1500 35 1800 42 1900
5 20* 1000 35* 1300 43 2300
Cortona Guided Walking Tour (1.5 Hours)
6 9* 300
16 400

* 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 36 years, Backroads has been perfecting the art of active travel. We are the Tuscany & Umbria 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

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Arezzo, Italy/Florence, Italy

Detailed Itinerary

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Trip Notes

All meals included except 2 lunches, 1 dinner

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