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Tuscany & Umbria Bike Tour

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

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 waxed hyperbolic on the glories of Umbria and Tuscany for centuries - how can you not have preconceived notions? 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 springtime poppies. Summertime sunflowers. Harvest-ready grapes in the fall. By the symphony of flavors in even the simplest of dishes. And the sheer warmth and passione of the local people. 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 Beauty abounds in Assisi, from the stunning Basilica of Saint Francis to the verdant valley below.

Day 3 Welcome to Tuscany!  Taste splendid wines, like Sagrantino, Montefalco Rosso and Vino Nobile di Montepulciano  Imagine you're in a postcard as you pedal along a sinuous ribbon of road flanked by bright red poppies, cypress trees and undulating hills Spin through the Orcia Valley, where fortified towns and distant Mount Amiata provide a dramatic backdrop Explore Pienza, the Renaissance utopia of Pope Pius II - and birthplace of heavenly pecorino cheese  Join our friend Vittorio in his cozy cantina for a private degustazione We're welcomed like family at La Chiusa - you'll understand why we've been coming here for years!

Days 4-6 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 Giovanni, our longtime local guide, leads us through this celebrated town  Savor a classic Tuscan tableau during an easy ride past ancient farmhouses, vast wheat fields and cypress-lined roads.

Guests Reviews About This Trip

For us it was a truly amazing and educational experience. Loved the physical challenge, loved the cultural interactions and loved the way that the Backroads team made it appear effortless and that we were the only riders on the road, the only customers at the hotels and restaurants. A joy, every minute of it.
Robert Allison
This trip was wonderful! Our leaders were fabulous, the cycling was just challenging enough. The hotels were very comfortable, and the service was excellent. And the countryside was so incredibly beautiful - the food, the people - something I will remember for a very long time.
Barbara Page - San Marcos, CA
This truly was a remarkable, memorable trip. I feel that biking allowed us to truly experience Italy in an intimate way. We met people on the roadside picking mushrooms...we could see Tuscany, feel Tuscany, and smell Tuscany!
Marianne Kaluza - Sammamish, WA

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)

Relais La Chiusa
Relais La Chiusa

Montefollonico (1 night) The Hideaway Report describes this welcoming country inn as a "family-run stone manor that looks across to the medieval hill town of Montepulciano." 

La Corte dei Papi
La Corte dei Papi

Cortona (2 nights) An enthusiastic welcome awaits at this superbly appointed 18th-century country house, rated one of the top hotels in Italy. (pool)

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 $6,198 pp dbl. occ. 8 - 9 guests $4,898 pp dbl. occ.
4 - 5 guests $5,598 pp dbl. occ. 10 - 11 guests $4,298 pp dbl. occ.
6 - 7 guests $5,098 pp dbl. occ. 12 or more guests $3,998 pp dbl. occ.

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 16 600 24 1300
2 12* 100 25* 200 54 900
3 20* 1200 27 1600 37 2500
4 21* 500 32 600
5 18* 300 28 500 39 800
Cortona Guided Walk (1.5 Hours)
6 8 100

* 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.


Premiere Inns

6 days, 5 nights
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Trip Price**
  • $4,198 to $4,798 pp dbl. occ.
  • (+$640 for sgl. occ.)

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Arezzo, Italy/Florence, Italy

Detailed Itinerary

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Dates & Prices

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2014 Classic 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.