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Tuscany & Umbria Bike Tour
Tuscany & Umbria Bike Tour

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.

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
big map

Premiere Inns

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

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

2014 Dates & Pricing*

  • 4/27-5/2 Price: $4298 pp dbl. occ., (+ $640 for sgl. occ.)
  • 5/18-23 Price: $4498 pp dbl. occ., (+ $640 for sgl. occ.)
  • 5/25-30 Price: $4798 pp dbl. occ., (+ $640 for sgl. occ.)
  • 6/1-6 Price: $4498 pp dbl. occ., (+ $640 for sgl. occ.)
  • 6/8-13 Price: $4398 pp dbl. occ., (+ $640 for sgl. occ.)
  • 6/15-20 Price: $4498 pp dbl. occ., (+ $640 for sgl. occ.)
  • 6/22-27 Price: $4798 pp dbl. occ., (+ $640 for sgl. occ.)
  • 6/29-7/4 Price: $4198 pp dbl. occ., (+ $640 for sgl. occ.)
  • 7/6-11 Price: $4598 pp dbl. occ., (+ $640 for sgl. occ.)
  • 7/13-18 Price: $4198 pp dbl. occ., (+ $640 for sgl. occ.)
  • 7/20-25 Price: $4498 pp dbl. occ., (+ $640 for sgl. occ.)
  • 8/3-8 Price: $4298 pp dbl. occ., (+ $640 for sgl. occ.)
  • 8/10-15 Price: $4298 pp dbl. occ., (+ $640 for sgl. occ.)
  • 8/17-22 Price: $4398 pp dbl. occ., (+ $640 for sgl. occ.)
  • 8/31-9/5 Price: $4198 pp dbl. occ., (+ $640 for sgl. occ.)
  • 9/9-14 Price: $4498 pp dbl. occ., (+ $640 for sgl. occ.)
  • 9/14-19 Price: $4498 pp dbl. occ., (+ $640 for sgl. occ.)
  • 9/16-21 Price: $4298 pp dbl. occ., (+ $640 for sgl. occ.)
  • 9/21-26 Price: $4698 pp dbl. occ., (+ $640 for sgl. occ.)
  • 9/23-28 Price: $4398 pp dbl. occ., (+ $640 for sgl. occ.)
  • 9/28-10/3 Price: $4198 pp dbl. occ., (+ $640 for sgl. occ.)
  • 9/30-10/5 Price: $4298 pp dbl. occ., (+ $640 for sgl. occ.)
  • 10/5-10 Price: $4198 pp dbl. occ., (+ $640 for sgl. occ.)
  • 10/12-17 Price: $4398 pp dbl. occ., (+ $640 for sgl. occ.)
  • 10/14-19 Price: $4198 pp dbl. occ., (+ $640 for sgl. occ.)
  • 10/19-24 Price: $4198 pp dbl. occ., (+ $640 for sgl. occ.)

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

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

  • 2 - 3 guests $6,198 pp dbl. occ.
  • 4 - 5 guests $5,598 pp dbl. occ.
  • 6 - 7 guests $5,098 pp dbl. occ.
  • 8 - 9 guests $4,898 pp dbl. occ.
  • 10 - 11 guests $4,298 pp dbl. occ.
  • 12 or more guests $3,998 pp dbl. occ.

Guest Trip Reviews

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

After taking our first Backroads trip to Provence last year, we were hooked. The level of planning, organizing and taking care of the guests on these trips is outstanding and does not go unnoticed!! It is amazing how every detail has been worked out to give the guest the best experience.
Jennifer Cohen - Edgewater, NJ

Absolutely the best trip that I have ever been on and quite possibly the best week of my life. It was really a great experience.
David Dines - Wayzata, MN

This was an incredible experience. The combination of cycling, food, wine and scenery made this one of our best vacations ever. The guides were all outstanding.
Bill Poston - Matthews, NC

One of the very best trips my wife and I have ever taken. I would highly recommend it to anyone who wants to see the Tuscany region in a wonderful active way.
William Miller - Fort Collins, CO

I had the most amazing vacation. Everything was perfect. The leaders were fantastic.
Fernanda Bratz

The leaders, the varied activities, the van support, the collective personality of the group made this my most special Backroads trip.
Judy Stark - Phoenix, AZ

Where to begin??? The trip provided a good balance of comfort vs. adventure, organized vs. free time and active group vs. individual downtime. The local staff, guides and hosts were all superb. The leaders were each warm, cheerful and highly professional; infinitely capable, flexible and dedicated to the needs of participants; and always demonstrated a positive and encouraging attitude no matter the situation or challenge. I felt like I was in a delightful movie the whole time; I loved every minute and looked forward to each new day/scene.

As for the value relative to the price, what would you pay for a trip of a lifetime and lifelong blissful memories, made possible by the local relationships, trip design, participant preparation and services, and the excellent quality of staff you provide?
Elizabeth Levitas - Raleigh, NC

This trip and our amazing guides met every expectation me and my husband had. I cannot say enough positive things about our leaders and their incredible knowledge of the area we were in and their efforts to help make this trip a trip of a lifetime. Both my husband and myself do a fair amount of biking but did not want to bike all day, every day. This trip was designed perfectly for our needs in that respect. Would recommend it for bikers and newbie bikers as well.
Stacey Starr - Suffern, NY

Even better than my high expectations. The value of this Backroads trip can't be overstated. So much for your money...especially when vacation time is scarce. Leaders on this trip worked together so well and created a friendly yet professional atmosphere that made it easy for the guests to relax and enjoy each other's company. Great chemistry all around on this trip.
Corbin Bennett - Oakland, CA