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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
  • Get to know our favorite friends and colorful locals

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 Spello, perhaps pausing to browse for ceramics, linens and olive wood pieces  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 châteaux is set amongst 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

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

Trip Dates & Prices

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

2015 August
2015 September
2015 October
2016 April
2016 May
2016 June
2016 July
2016 August
2016 September
2016 October

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 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 $6,298 pp dbl. occ. 8 - 9 guests from $4,998 pp dbl. occ.
4 - 5 guests from $5,698 pp dbl. occ. 10 - 11 guests from $4,498 pp dbl. occ.
6 - 7 guests from $5,298 pp dbl. occ. 12 or more guests from $4,198 pp dbl. occ.


2 - 3 guests from $6,398 pp dbl. occ. 8 - 9 guests from $4,998 pp dbl. occ.
4 - 5 guests from $5,598 pp dbl. occ. 10 - 11 guests from $4,498 pp dbl. occ.
6 - 7 guests from $5,198 pp dbl. occ. 12 or more guests from $4,198 pp dbl. occ.

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

For 36 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 1-4


Arezzo, Italy/Florence, Italy

Detailed Itinerary

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Trip Notes

All meals included except 2 lunches, 1 dinner

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