Backroads Tuscany & Umbria Walking & Hiking Tour
Walking tour in Tuscany and Umbria, Italy
Backroads Tuscany & Umbria Walking & Hiking Tour
Dining on Backroads Tuscany & Umbria Walking & Hiking Tour
Italian Food and Wine - Backroads Tuscany & Umbria Hiking Tour
Backroads Tuscany & Umbria Walking & Hiking Tour
Walking & Hiking
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Tuscany & Umbria Walking & Hiking Tour

Ancient Footpaths: Assisi & Cortona to Florence

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.

THIS ITINERARY: 6 days, 5 nights


FROM: $5,049 - $5,149 pp dbl occ
($1,100 for sgl occ)

Tuscany and Umbria walking tour map
Tuscany and Umbria walking tour map


Start Orte / End Florence

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

  • Hike central Italy's grand and inspiring Apennines, Val d’Orcia and Chianti, sampling legendary culinary riches along the way
  • Relish incredible local cuisine in picturesque Norcia, an ancient-walled town famous for delicious regional flavors
  • Discover world-class Umbrian and Tuscan wines like Sagrantino, Vino Nobile di Montepulciano and Chianti Classico
  • Walk through a magnificent landscape to the extraordinary World Heritage sites of Assisi, Val d'Orcia, and Pienza 
The Backroads Experience
The Backroads Experience
Backroads Walking & Hiking Trips
Backroads Walking & Hiking Trips
Backroads Trip Leader
Meet Our Leaders
Accommodations may vary based on departure date.
6 Days Premiere Hotels
Accommodations may vary based on departure.
Days 1-2

You’re in Italy’s Green Heart, so called for its agricultural riches—get ready to savor black truffles, salamis and rare mountain formaggi (cheeses) | Wander through Norcia’s idyllic 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 | Relish unforgettable Umbrian wines and haute cuisine at the Bianconi family’s Michelin-starred Vespasia restaurant | Vacation at an enchanting Relais & Château hideaway.

Palazzo Seneca
Palazzo Seneca
| Premiere Hotel

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)

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 | A one-of-a-kind stay awaits at our luxurious hotel.

Relais La Corte dei Papi
La Corte dei Papi
| Premiere Hotel

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)

Days 4-6

Deep in Tuscany, be immersed in 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 | Laze over cappuccinos, listening to locals swap stories in sleepy cobblestone villages | Extend your Italian vacation in incomparable Florence.

Castel Monastero
Castel Monastero
Monastero d'Ombrone
| Premiere Hotel

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

Dates & Prices

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

Click on dates for pricing, itinerary variations and to book your trip. Price is per person, double occupancy.

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Activity Level: 1-4

Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. Several routes and a range of levels are offered each day so you can choose how much or how little activity you want to do. Learn more about how we determine activity levels.

Route notes

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

Daily Route Options

Day 1
Walking & Hiking
Level 1 | 2 miles | 100 ft. gain
Level 2 | 5 miles | 100 ft. gain
Day 2
Walking & Hiking
Level 1 | 2 miles | 500 ft. gain
Level 2 | 4 miles | 800 ft. gain
Level 3 | 6 miles | 900 ft. gain
Day 3
Walking & Hiking
Level 1 | 3 miles | 600 ft. gain
Level 2 | 4 miles | 900 ft. gain
Level 3 | 7 miles | 1000 ft. gain
Walking Tour of Assisi
Day 4
Walking & Hiking
Level 2 | 4 miles | 700 ft. gain
Level 3 | 8 miles | 1000 ft. gain
Day 5
Walking & Hiking
Level 1 | 4 miles* | 600 ft. gain
Level 2 | 6 miles* | 900 ft. gain
Level 3 | 8 miles* | 1100 ft. gain
Level 4 | 9 miles | 1300 ft. gain
Day 6
Walking & Hiking
Level 1 | 3 miles | 300 ft. gain
* Includes shuttle.

What's Included

  • All breakfasts, 4 lunches, 4 dinners
  • 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

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Have a question and need expert advice? Our team of Trip Consultants is here to help! You can also visit our FAQ's.

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