Tuscany & Umbria Walking & Hiking Tour

Ancient Footpaths: Assisi & Cortona to Florence

From $5,049 pp dbl. occ. | 6 days / 5 nights

Call for single supplement pricing

Tuscany and Umbria must be experienced up close. Taste the traditional recipes and fine wines. 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.

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Start Orte / End Florence

Start/End locations may vary. Do not book flights until your trip details are confirmed.

Tuscany and Umbria walking tour map


  • Hike central Italy's unforgettable and inspiring Apennines, Val d'Orcia and Chianti, savoring legendary culinary riches along the way
  • Relish incredible local cuisine in picturesque Norcia, an ancient-walled town famous for delicious regional flavors
  • Taste world-class Umbrian and Tuscan wines like Sagrantino, Vino Nobile di Montepulciano and Chianti Classico
  • Ramble through a magnificent landscape to the extraordinary World Heritage sites of Assisi, Val d'Orcia, and Pienza 

Start Orte / End Florence

Start/End locations may vary. Do not book flights until your trip details are confirmed.

Tuscany and Umbria walking tour map


Days 1-2 You're in Italy's “green heart,” so called for its agricultural riches—savor black truffles, salamis and rare mountain formaggi (cheeses) | Stroll through Norcia's picturesque medieval center, the birthplace of St. Benedict and a significant center of modern monasticism | Hike a ridge trail up to the top of Monte Abuzzago where spectacular views of the high alpine landscape await | Savor unforgettable Umbrian wines and haute cuisine at the Bianconi family's Michelin-starred Vespasia restaurant | Unwind at our enchanting Relais & Château hideaway.

Day 3 Follow an ancient pilgrimage route to the World Heritage city of Assisi, nestled on the flanks of Monte Subasio | Take time to explore the Gothic and Romanesque architecture in what was once the home of St. Francis | Visit historic hilltop Cortona, surrounded by 3,000-year-old Etruscan walls, and the setting for Under the Tuscan Sun.

Days 4-6 Deep in Tuscany, discover the picture-perfect landscape of the Val d'Orcia | Have a look around Renaissance-style Pienza, a World Heritage site, perhaps stopping to try the superb local pecorino cheese | Discover the rustic beauty of Chianti, hiking through the vineyards where the famed wine is produced | Learn everything about the antique Black Rooster League and the centuries-long war between Florence and Siena | Linger over cappuccinos listening to locals swap stories in sleepy cobblestone villages | Extend your Italian vacation in incomparable Florence.

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. View cancellation policy.

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

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  • Private Trip
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C Classic Dates

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.

Private Trip Pricing
  • 10 or more Guests: from $4,799 pp dbl occ
  • 9 Guests: from $5,299 pp dbl occ
  • 8 Guests: from $5,499 pp dbl occ
  • 2-7 Guests: Give us a call or reach out here!

Don't see your ideal travel date? Make a Date

View Scheduled Dates

Tell us what your dream trip would be and we'll make it happen! Whether you're looking for a honeymoon trip for 2, a 30-person family reunion or a 100-person corporate trip, we can do it all. A dedicated Custom Trip Consultant will work closely with you to bring your dreams to reality. Call us at 800-462-2848 to speak with your Custom Trip Consultant or click on the button below.



C Couples, Friends & Solos Tours


From $5,049 pp dbl. occ.
6 days / 5 nights

Call for single supplement pricing

Premiere Hotels

Palazzo Seneca
Palazzo Seneca

Norcia (2 nights)

Relais La Corte dei Papi
La Corte dei Papi

Cortona (1 night)

Castel Monastero
Castel Monastero

Monastero d'Ombrone (2 nights)

Activity Level

This trip is rated Levels 1-3

What's Included

Services and equipment are included.

Why Backroads

Why Travel with Backroads in Tuscany and Umbria

More On This Trip

Reviews by Power Reviews ®

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Premiere Hotels

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 View Scheduled Dates or Private Dates tabs.

Palazzo Seneca

Palazzo Seneca

Norcia (2 nights)

Housed in an artfully restored 16th-century palace, this elegant hotel is the perfect place to unwind and discover Umbria. A Relais & Châteaux member. (spa)

Relais La Corte dei Papi

La Corte dei Papi

Cortona (1 night)

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)

Castel Monastero

Castel Monastero

Monastero d'Ombrone (2 nights)

Stunning views of the Tuscan countryside and exceptional hospitality await at this elegantly restored castle-hotel. (pool, spa)

This Trip Is Rated Levels 1-3

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 (drag to see full )

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 2 100 5 100
2 2 500 4 800 6 900
3 3 600 4 900 7 1000
Walking Tour of Assisi
4 4 700 8 1000
5 4* 600 6* 900 8* 1100 9 1300
6 3 300

Note: The terrain on this trip includes vineyard footpaths and wooded trails.

* Includes shuttle.

Learn more about how we determine our activity level and fully support a range of abilities and interests.

Please note that our distance and elevation figures come from Ride with GPS. Other sources may give differing elevation figures due to different GPS and mapping technologies and other external factors.


All breakfasts, 4 lunches, 4 dinners

Also Included

  • Expertise and services of our experienced Trip Leaders
  • Snacks and beverages between meals
  • Additional guides and experts from the region on many trips
  • Van shuttles to support a variety of route options
  • Comprehensive Travel Planner with detailed pre-trip information
  • Private guided tours at museums, historic sites, wineries and other select attractions as noted in the Travel Planner
  • All gratuities at hotels and restaurants
  • Special events, including wine tastings and other select attractions as mentioned in the Travel Planner
  • On biking and multi-adventure trips, use of fully equipped Backroads titanium bike plus helmet and accessories
  • Trailercycles, carriers, and kid-sized helmets for Family Trips
  • Equipment and experienced guides for kayaking, rafting, snorkeling, sailing and canoeing as described
  • Park and other entry fees
  • Fares for trains, ferries and other modes of travel as listed in the Travel Planner
  • Select coach transfers
  • Baggage transfers and porterage

Get the Straight Talk about This Trip

We want to make sure you're on the right trip and that you have the best experience possible. Every Backroads trip is unique and this one is no exception.

Why Travel with Backroads in Tuscany and Umbria

Our Cultural Roots Run Deep

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.

Only the Best Hotels

On this trip featuring Premiere Hotels, 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.

We Speak the Language

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.)

A Variety of Routes Each Day

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.

We Live in the Neighborhood

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.

The Best Leaders in Tuscany and Umbria

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.

In Europe Since 1988

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.