Tuscany must be experienced up close. Taste the Brunello. Breathe in the aroma of bread toasting in a stone fireplace, glistening with freshly pressed olive oil. Stroll through vineyards and hilltop towns. Let your eyes linger on ancient villas. Imagine the possibilities. There is no better—or closer—way to experience the heart of Italy.
Days
1-2 Foodies, rejoice! You're in Italy's "green heart," so called for its agricultural riches —savor black truffles, taste salamis and sample rare mountain formaggi (cheeses) 
Walk in the Topino river valley among sunflowers and vineyards en route to medieval Montefalco Sample Sagrantino, Umbria's most prized vino rosso, at an exclusive tasting Soak up breathtaking panoramas of Assisi from Montefalco's commanding hilltop position Discover the flavors of strangozzi al tartufo (pasta with black truffle sauce) and other hearty Umbrian dishes.
Days
3-4 Follow an ancient pilgrimage route to the World Heritage city of Assisi, nestled on the flanks of Monte Subasio, as you admire flowering oak groves and vast valley views along the way Take time to explore the Gothic and Romanesque architecture in what was once the home of St. Francis Deep in Tuscany, discover the picture-perfect landscape of the Val d'Orcia Journey on age-old paths in the land of the Tuscan sun to charming Cortona for a guided visit of town Have a look around Renaissance-style Pienza, perhaps stopping to try the superb local pecorino cheese Delight in traditional Tuscan cuisine at a winery-hosted dinner in the Brunello region.
Days
5-6 On foot to Montalcino, rows of vineyards and wildflower fields greet you at every turn Visit the Abbey of Sant'Antimo and be welcomed at charming agriturismi (working farms) Relish some of the world's finest wines in memorable Montalcino and a superb dinner at Settimo Senso, our hotel's outstanding restaurant.
This trip introduces you to two fantastic regions: Umbria first, then Tuscany. While 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 finest walking & hiking opportunities that we offer!- Italy
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Accommodations may vary based on departure date. Any difference from what is listed below can be found by clicking on your desired date on the Dates & Prices tab.
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Overlooking the charming Piazza del Comune, art and sophistication abound at this spacious former Renaissance palace. (spa)
Feel welcomed like family by owner David Papi at this refined and superbly appointed 18th-century country home, rated one of the top hotels in Italy and a Backroads-exclusive property. (pool)
Soak up superb hilltop views at this elegant 11th-century fortress featuring a magnificent vantage point above the Val d'Orcia. A Small Luxury Hotels of the World member. (pool, spa)
There's no better way to find out about Backroads than by hearing it from the people who have traveled with us. For more about the Backroads Experience, read our Guest Testimonials.
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Comments about Tuscany & Umbria Walking & Hiking Tour:
This trip introduces you to two fantastic regions: Umbria first, then Tuscany. While 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 finest walking & hiking opportunities that we offer!
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The earlier you book, the more choice you'll have and the lower your price. And you can always change your mind—you won't be charged to transfer to a different trip before your final payment is due.
Please click on a date below for specific pricing and possible itinerary variations.
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AVAILABLE TO BOOKi GOING FASTi CONTACT USi PRIVATE TRIP - RESERVEDi
Interested in a Private Trip? Check out the Make It Private tab for private dates available, or call us at 800-462-2848.
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.
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| Daily Route Options | ||||||||||
| Day | EASYGOING | ACTIVE | AVID | |||||||
|---|---|---|---|---|---|---|---|---|---|---|
| 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 | 3* | 500 | 5 | 900 | ||||||
| 2 | 2* | 200 | 4 | 300 | 6 | 700 | 7 | 2000 | ||
| 3 | 3* | 500 | 7 | 2000 | ||||||
| Walking tour of Cortona in morning | ||||||||||
| 4 | 3* | 400 | 4* | 600 | 6* | 900 | 8 | 1000 | ||
| 5 | 3* | 300 | 5* | 400 | 6* | 1100 | 8 | 1300 | ||
| 6 | 3* | 200 | 4 | 700 | ||||||
Note: The terrain on this trip includes vineyard footpaths and wooded trails.
* Includes shuttle.
Learn more about how we determine our activity levels and fully support a range of abilities and interests.
Please note that our distance and elevation figures come from Ride with GPS. Other sources (such as Map My Ride and Garmin devices) may give differing elevation figures due to different GPS and mapping technologies. Readings from a Garmin or a smart phone are influenced by other factors such as air pressure.
Thanks to our extensive connections in Tuscany and Umbria, Backroads takes you off the beaten track and deep into the region's culture in ways that traditional travel can never hope to do. We know the people and their customs, the legacy of art and architecture, the complex history and politic—and if we're not sure, our amazing local experts can fill in the blanks.
On this Premiere Inn trip, you can count on the best lodgings Tuscany and Umbria has to offer. In fact, the hotels we've chosen in this region have higher retail room rates than those offered by any other active travel company—even when their trips cost more.
If we told you many companies' leaders can't actually speak the language where they lead trips, you'd say incroyable... ridicolo... không the tha thú. At Backroads, fluency in the local language is a given. Find out more on the best leader recruitment, training and development in the business. (And by the way, that was "unforgivable" in Vietnamese.)
In Tuscany and Umbria you head off each morning after choosing among several expertly designed routes—all with detailed directions, mileage and shuttle options. Unlike trips with one fixed daily route (or worse, one guide that everyone's obliged to follow), you're free to enjoy the best of the region at your pace, stopping wherever you want to explore further.
Our Trip Leaders in Tuscany and Umbria live in the area and are deeply engaged in their communities, giving them unique inside knowledge they're happy to share in making your experience that much richer. They'll introduce you to people, customs and parts of town you'd likely never encounter on your own—and teach you a few local phrases to help break the ice.
Backroads has the best-qualified people to lead your trip in Tuscany and Umbria, and our guests back that up, rating our Trip Leaders an average of 9.75 out of 10 for all-around quality of performance. Get the facts (and no fluff) on how we recruit and develop the very best people for your trip.
Backroads has been welcoming active travelers to Europe since before the Berlin Wall came down. Today it's virtually our second home. We know the perfect roads and trails, the most scenic valleys and hilltop towns, the hidden churches and gem-like museums, the up-and-coming vintners and celebrated chefs—and, of course, all the best places to stay.
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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 the selection of dates below for your group; some dates are only available for 16 or more guests while other dates are available for 8 or more guests. If your party has fewer than 8 guests, or your preferred date is not available, we'll create a departure just for you. Call or email us to reserve your date.
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8 AVAILABLE TO BOOK FOR 8 OR MORE GUESTS 16 AVAILABLE TO BOOK FOR 16 OR MORE GUESTS RESERVED
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Invite your family and friends on an adventure that's entirely your own - for your group of 8 or more. Find out more
I simply can't imagine a better way to immerse yourself in the life of a region, to explore hidden corners and appreciate nuances while enjoying the benefits and enormous satisfaction of traveling under your own power. These are experiences you cannot have behind the wheel of a car, or on a train or a tour bus. Active travel is, at its heart, a way of connecting more authentically with the world. Sure, Backroads provides amazing leaders, superb accommodations and meals, and opportunities you could never arrange on your own. But all of our comprehensive planning and support is aimed at something far simpler: bringing you the immediate, highly personal satisfaction of discovering a new world on your own terms.
— Tom Hale, Founder & President
