Italy: Tuscany & Umbria

Guided Walking Tour, Italy: Tuscany & UmbriaGuided Walking Tour, Italy: Tuscany & Umbria


Tuscany & Umbria


To understand Italy’s philosophy of life, you must eat like an Italian. Happily, the great Umbrian tradition of fine food and wine figures prominently on this tour. You’ll dine in Ristorante Camesena, where specialty dishes provide an exceptional culinary experience. The region’s generous hospitality is coupled with classic Italian scenery and ancient history in the Renaissance hill town of Pienza. Visit the 15th-century convent of Sant’Anna. Stroll Spello, a walled medieval wonder with Roman roots. Admire the magnificent art museum in Gubbio’s 14th-century Palazzo dei Consoli. The summit of Mt. Subasio offers splendid views and one of the finest walks in all Italy. In the lush valleys of Tuscany and Umbria, historic chapels sit in charming seclusion among grapevines and olive trees. Fresco master­pieces, Roman aqueducts, Etruscan ruins, historic abbeys―you’ll enjoy a grand buffet of Italian culture along with tastings of cheeses, olive oil, truffles, wine, and other local delicacies that fill every day with unique flavor.

Flight + Tour Combo NEW!

Flight + Tour Combos complement our Guided Walking Adventures with advantageous priced round-trip airfare, pre- and post-tour accommodations, overseas tour transfers, and breakfasts. They give you everything you need in one convenient package; we handle all the details.

View 2015 Dates + Prices »
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Add a Tour Extension to Your 2016 Flight + Tour Combo

Pre-Tour Extension: Florence

2 nights: $248 | Single +$148
Delight in the world-renowned art, history, culture, and cuisine of this legendary city on the Arno River. From the Ponte Vecchio to the Medici art treasures of the Uffizi, you’ll have time to experience it all.

Post-Tour Extension: Rome

2 nights: $348 | Single +$248
Feel the ebb of three thousand years of living history— a melánge of Roman ambition, baroque decadence. You’ll have freedom to experience the city’s countless monuments at your own pace.

View 2015 Flight + Tour Combo Itinerary »
2016 Flight + Tour Combo Itinerary Coming Soon!

Activity Level
Easy to moderate;
4-8 miles daily
Florence, Italy
Orvieto, Italy
Daily Itinerary
Download printable
Reading List
pre-trip reading
Guided Walking 
7 days, 6 nights Trip Includes 

Trip Includes

  • Two expert, local guides (for groups of 8 or more), with you 24/7
  • All meals except for two dinners; local wine included
  • All accommodations while on tour
  • Transportation from the meeting point to the departure point
  • Entrance fees and special events as noted in the itinerary
  • The unbeatable and cumulative experience of the Country Walkers staff
per person double occupancy
Single supplement + $350

Solo surcharge + $0

2016 Single Supplement + $398

Call 800.234.6900 to book this trip.

Number of Travelers
Total in your party
Price From
per person double occupancy

Call 800.234.6900 to book this trip.



Itinerary and Accommodations

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Day 1


Arrival in Florence. Transfer to Siena. City tour of Siena; 2 hours, easy (sneakers acceptable). Transfer to Montalcino

After meeting in Florence, you transfer to Siena. The week begins with a walking tour of the historic center of Siena, the atmospheric Tuscan city. With its mixture of Gothic and Romanesque architecture dramatically set on three hills, Siena rivals Florence not only in beauty but also in culture. Following a light lunch of Sienese specialties, you explore the world-famous Campo square, presided over by the impressive town hall and tower. The Campo is the setting of the celebrated Palio horse race. Your engaging local guide leads you to the Duomo, the main cathedral, with its striking marble façade.

Later you transfer to Montalcino, your home for the next two nights. Unchanged since the 16th century, Montalcino is a charming walled hilltop town and the birthplace of Brunello, one of Italy’s finest wines. A magnificent fortress built in 1361 crowns its heights. Your family-run hotel is located at the edge of Montalcino’s medieval walls, in the town’s quiet pedestrian zone—ideally situated to explore the town’s cobblestoned alleyways, stone houses, local shops, and cafés. You are welcomed with dinner in a warm, wood-beamed restaurant in the heart of town; a glass of Brunello may be paired with a tagliata fiorentina (local grilled beef), a perfect start to the week’s culinary delights.

Hotel Dei Capitani

Montalcino, Italy

Set in a 15th-century building at the edge of Montalcino’s medieval walls, this charming family-run hotel features comfortable rooms with wood-beamed ceilings and terracotta floors, stunning views of the Orcia and Arbia valleys, a large garden, and an outdoor, terraced swimming pool.

Day 2


Torrenieri to Pienza; 6 miles, easy to moderate. Optional afternoon walk from Bagno Vignoni; 2-3 miles, easy to moderate

Today’s exploration begins in the outskirts of Montalcino. After an initial short drive to the village of Torrenieri, a dirt lane meanders along rolling terrain between the Orcia Valley and the Crete Senesi (Sienese hills) toward Pienza, the morning’s destination.

Lunch awaits at an old Tuscan farmhouse, where your hosts welcome you with an assortment of local pecorino (sheep’s milk cheese), cold cuts, homemade preserves and pickles, accompanied by their house wine. Following lunch you are driven a few minutes away to Pienza, the birthplace of Enea Silvio Piccolomini, elected Pope Pius II in 1458. Envisioning the creation of the “ideal Renaissance town,” Pius II had the village renamed and entirely redesigned by Florentine architect Bernardo Rossellino. While the village’s restructuring came to a halt following Pius II’s death, the vision of Humanist urban space and planning was superbly realized in the town center, Piazza Pio II, where the main monuments lie harmoniously along the town’s main axis, the town hall opposite the 15th-century cathedral.

An optional afternoon walk departs from the tiny spa town of Bagno Vignoni, where you can soak your feet in the warm waters flowing out of the town’s picturesque main square—the only one in Italy that is, in fact, a thermal pool. After returning to the hotel in Montalcino, there is time to relax before walking to dinner in the center of town. There we will join local couple Lina and Domenico for an aperitivo in their garden and simple yet tasty meal in their centuries-old home.

Hotel Dei Capitani

Montalcino, Italy

Set in a 15th-century building at the edge of Montalcino’s medieval walls, this charming family-run hotel features comfortable rooms with wood-beamed ceilings and terracotta floors, stunning views of the Orcia and Arbia valleys, a large garden, and an outdoor, terraced swimming pool.

Day 3


Montalcino to Sant'Antimo Abbey; 4-7 miles, easy to moderate. Transfer to Umbria; approximately 2 hours

Today you depart Montalcino on foot. You walk through gentle hills, in the shade of old-growth woods, and skirt vineyards where the famous Sangiovese Grosso grape is grown for Brunello wine. You might stop to visit an ancient Etruscan settlement, still under excavation, before continuing through farmland, ancient dwellings, wineries, and olive groves to make the dramatic descent to the isolated Romanesque Abbey of Sant’Antimo.

After a truly authentic lunch of pink risotto and wild boar stew, you leave southern Tuscany; the drive winds through the rolling hills and medieval hilltop villages of the Crete Senesi, then descends on the plains surrounding Lake Trasimeno and enters the main valley of Umbria, a region known as the “Green Heart of Italy.”

Your home for the next four nights—an elegant, centrally located 16th-century property—is in Spello, a walled Roman and medieval town. Time permitting upon check-in, a short introductory walking tour provides an orienteering overview. This evening, an independent dinner awaits with your guides’ advice; perhaps a lively local trattoria or a glass of Sagrantino red wine, Umbria’s answer to Brunello, served alfresco on the terrace of your hotel.

Hotel La Bastiglia

Spello, Italy

Located in a former 16th-century grain mill in the walled medieval town of Spello, this elegant hotel boasts a wide terrace with panoramic views overlooking the Chiona Valley and outdoor swimming pool.

Day 4


Assisi city tour; 2 miles, easy. Countryside of Assisi; 3-4 miles, easy to moderate

The morning and early afternoon are devoted to an exploration of Assisi. This stunning town sits in a commanding position on the slopes of Mount Subasio and has retained its charming medieval qualities and strong associations with St. Francis. You tour its multifaceted historical center and the Basilica of St. Francis with a local guide. After lunch at a local pizzeria, there is time for independent exploration of its narrow lanes and inviting shops.

The afternoon offers several options. You may choose to spend more time in Assisi on your own, return to Spello to stroll its picturesque alleys or to relax at the hotel. Alternatively, an easy walking option is offered—this time venturing out of town into the lush, surrounding countryside and olive groves, all the way back to Spello. Dinner this evening is at an intimate restaurant, where you are welcomed with a glass of crisp prosecco on a panoramic terrace overlooking the Umbrian plain.

Hotel La Bastiglia

Spello, Italy

Located in a former 16th-century grain mill in the walled medieval town of Spello, this elegant hotel boasts a wide terrace with panoramic views overlooking the Chiona Valley and outdoor swimming pool.

Day 5


Gubbio; 5-7 miles, easy to moderate

Gubbio, the medieval masterpiece of Umbria, charms with its intimate alleys and surprisingly spacious panoramic piazza, flanked by the stunning palazzo comunale. Following a scenic drive, the morning walk’s destination is the Church of Saint Ubaldo, perched high on the mountainside overlooking Gubbio. The church is the end point of the annual “Race of the Ceri,” a colorful historical festival where locals race ceri (giant heavy wooden structures that resemble candlesticks). The walking route passes by limestone outcrops and a tiny chapel, meandering through woods, along a creek, and up a narrow gorge. A lunch of regional specialties awaits at a local restaurant. After lunch, you are free to wander around the historical center and perhaps visit the stunning 14th-century town hall, the Palazzo dei Consoli, with its renowned art museum. Or you may choose to absorb the atmosphere of this Umbrian gem over a gelato or caffé before the return drive to Spello. Your guides provide ideas for dinner on your own in town; the restaurant or trattoria menu may offer chickpea soup drizzled with olive oil, bruschetta, or strangozzi, the regional square-shaped spaghetti.

Hotel La Bastiglia

Spello, Italy

Located in a former 16th-century grain mill in the walled medieval town of Spello, this elegant hotel boasts a wide terrace with panoramic views overlooking the Chiona Valley and outdoor swimming pool.

Day 6


Assisi to Spello via the Natural Park of Mount Subasio; 5-9 miles, easy to moderate

After breakfast there is a short transfer to the Natural Park of Mount Subasio, a protected area with serene paths meandering through open meadows and oak and pine woods. Mount Subasio is the sprawling mountain on whose flank Assisi is built. A haven of subtle beauty and spirituality, it was here that St. Francis preached to the birds, all gathered on tree branches. Hiking in the meadows along the summit of the mountain, you are likely to see grazing herds of sheep, white Chianina cows, and semi-wild horses before descending to lunch in the small, charming hamlet of Collepino. The waiting table is spread with an ample antipasto of assorted bruschetta, followed by grilled meats and vegetables.

After lunch you may choose to return to Spello by van or to descend on foot, continuing through olive groves and alongside the ancient Roman aqueduct that once brought drinking water into town along the eastern side of the mountain.

This evening’s farewell dinner is at the Locanda del Cardinale in Assisi, where they’ve glassed in a remarkable dig of Roman ruins and built a restaurant on top. You’ll dine on the finest Umbrian cuisine and toast your week’s adventures with a glass from the world-class wine cellar.

Hotel La Bastiglia

Spello, Italy

Located in a former 16th-century grain mill in the walled medieval town of Spello, this elegant hotel boasts a wide terrace with panoramic views overlooking the Chiona Valley and outdoor swimming pool.

Day 7


Easy city walking tour of Orvieto. Departure from Orvieto

You depart Spello for the picturesque city of Orvieto, situated atop an outcrop of tufo (compacted volcanic ashes). This final visit takes you to the main square and its magnificent Gothic cathedral, considered to be one of Italy’s most beautiful, with its intricate bas relief and mosaic-decorated façade. You may choose to stay in this pleasant pedestrian city or depart from Orvieto’s train station for short train connections to either Rome or Florence.

Itinerary Disclaimer

Bear in mind that this is a typical itinerary, and the actual activities, sites, and accommodations may vary due to season, special events, weather, or transportation schedules. We reserve the right to alter the itinerary since tour arrangements are made up to a year in advance, and unforeseen circumstances that mandate change may arise. Itinerary changes are made to improve the tour and your experience. If you are currently booked on a Country Walkers adventure, an itinerary has been sent to you for your exact departure date. Please call Country Walkers at 800.464.9255 if you have any questions about the exact itinerary or hotels selected for any of our tours.


Alessandro Gullo

Alex is a native of Italy with Sicilian ancestry. Educated in the U.S. as well as Italy, he is a certified guide of historic monuments in Umbria. He combines his charming personality with a vast knowledge of culture, art, history, food, and wine on many of our vacations in Italy.

Elizabeth Namack

With her warm smile, Elizabeth brings her love of all things Italian to tours in Tuscany, Umbria, and the Cinque Terre. She first came to Italy, and more specifically to Florence, as an American college student to study Italian art history and language. Well, that was almost twenty years ago and she never left! Her active lifestyle and interest in regional wines and cuisines—coupled with her academic background in art history and painting restoration—all help make getting up those hills a little easier—there is a lot to talk about!

Manuela Ciri

Manuela was born and raised on a farm in Umbria where she has been involved in leading cooking lessons and olive-oil tastings. Educated both in Italy and in the U.S., she is a botanist, herbal healer, and certified environmental guide; her vast knowledge of nature, agriculture, and traditional food is warmed by her sunny smile and joyful nature. This multi-talented guide also has her captain’s license and can often be found in Croatia—her home away from home. She has sailed the Adriatic numerous times and is passionate about the language, culture, and people. In her ‘spare’ time, Manuela teaches environmental education and works on landscape engineering projects.

Keegan Alagna

With his American mother and Sicilian father, Keegan Alagna grew up in a bilingual home in the Umbrian countryside near Assisi. From his childhood on a working farm to post-graduate work in geology, he has always pursued his passion and curiosity for the outdoors, through teaching, guiding, and exploring. He brings his depth of knowledge of geology, nature, Italian history and culture to his walking tours and to his position as a board member on Italy’s premier outdoor group—the CAI, the Club Alpino Italiano.

Guest Comments

K. Alley, California, May 2014

This trip was everything that we hoped it would be. The guides, the group, the food and the accommodations were all first class.

J. Langsdon, California, May 2014

It was very personal. I love eating in people’s homes, family run wineries, & going to visit Alessandro’s friend, Roy Grant, to see his home & Middle Age religious art. Alessandro & Manuela made it very special, even to the point of us hiking thru the streets in Assisi & going by his kids’ schools to wave & say hello. Deep into the culture & the food was exquisite.

S. Kosiur, Washington, May 2014

Excellent well thought out, well planned tour. Beautiful countryside and vistas, outstanding food and dining atmosphere, excellent services, very professional guides, and great walks.

M. Soss, Ney York, May 2014

Walking with Alessandro and Manuela through Tuscany and Umbria was stimulating, fun and an extraordinary gastronomic experience! Their passion and enthusiasm for the region was contagious. We felt at home and with family for the entire tour. From the moment they greeted us to the moment they said good bye we were part of the Country Walkers family.

D. & T. Work, Pennsylvania, September 2014

We enjoyed a blissful week with beautiful countryside, a variety of walking options, a variety of things to see, the most cohesive group with which we have walked, and two passionate guides.

E. Howe, Massachusetts, May 2014

I loved the walks, the guides, the food, everything. The scenery was beautiful and every walk was a little different.

R. Natelson, New Jersey, May 2014

Aside from having a wonderful group to share our experiences, this tour of Tuscany/Umbria was tremendous. The beauty of the region, its long history from Roman times, the spiritual legacy manifested by the lives of St. Francis and St. Clare, the enduring traditions of the people, and the incredible food.  Our tour guides, Manuela and Alex, brought everything together in a very special and memorable way.  Both are experts of the region, with a masterful gift of communicating their knowledge and helping us to understand the harmony of the land, the wildlife and the local people. I feel privileged and grateful to have had Manuela and Alex as our guides on this Country Walkers tour and recommend it highly to travelers wishing to truly appreciate the harmony and beauty of this land.

C. & W. Oster, Oregon, May 2013

After reading all the literature and looking at the beautiful photographs I had this trip pretty hyped up in my mind...and it didn't disappoint! In fact, the week exceeded our expectations.

K. Egge, Illinois, May 2013

I was very please with the historical commentary and regional knowledge of our guides. It made sightseeing much more interesting to have in-depth explanations from knowledgeable individuals. This is something one could never get from just reading books and brochures. Exceptional dining as well. Several locations chosen for dining were remote and/or unique and I can't imagine ever finding restaurants like these on my own. The food and wine was just fabulous!

R. McKittrick, Maine, October 2012

Every aspect of our trip was pleasant, from the evident thorough planning, to venues and trails, to adjustments "on the fly" by our excellent guides, when weather threw us a curve ball. Both guides, Alessandro ("Alex") and Manuela, were very personable, friendly, fun, and highly knowledgeable. They complemented one another well, ably covering the spectrum from history, architecture, art, religious history, food, wine (very important!), to flora and fauna, climate—even edible mushrooms.  

B. Simone, Pennsylvania, May 2012

This was my very first CW tour and for me it was the trip of a lifetime. It really was life changing for me. Not only the tour itself but also all of the people I met on the trip. Everything about this trip was exceptional. It was without a doubt the best trip I have ever been on. CW is a great company, thank you for this experience.

S. Heine, California, May 2012

I loved every minute of this tour. The accommodations were very comfortable, the food was superb and the guides made my experience very special. Alex has the wonderful ability to make the history of Italy come alive and his enthusiasm is contagious. He has a rare talent for connecting lives of past civilizations with us today. I would rate him one of the very best guides I've ever had anywhere. I found Manuela sweet, fun and efficient. She went out of her way to please and innovate, and she made all the logistics work out painlessly.

J. & B. McGovern, Wisconsin, October 2012

GREAT guides.  Alessandro and Manuela did everything they could to make our "walk" enjoyable, educational and fun.  Food/restaurant choices were "out of this world" good.

T, Chronister, North Carolina, May 2012

Guides were exceptional—very attentive to the preferences and abilities of the extremely varied group. Perfect mixture of walking, sightseeing, and dining.

A. Liberman, California, October 2012

Our CW guides, in particular Alessandro but also Manuela, brought excitement to every day—interesting discussions before and during every walk, selections of wonderful places to dine for every meal, insights on culture and history at every sightseeing opportunity. The trip made such a strong impression on me that it seemed I had spent two weeks in Tuscany and Umbria, not just one.

R. Liberman, California, October 2012

The final dinner in a superior restaurant with glass floors exposing a Roman villa replete with mosaics and artifacts was preternaturally amazing and rewarding. Our accommodations in Spello were fantastic with a suite including a large sitting room—this was a first in many walking tours! Alessandro was one of the best guides we've had—his fund of knowledge, enthusiasm, and charismatic way of communicating places him above most erudite professors.

T. Burton, California, September 2011

The Tuscany & Umbria tour exceeded all of my expectations. I loved it. The knowledge gained, culture and food experience was invaluable. The guides made the trip memorable and adventurous.

J. Dahms, Connecticut, October 2011

If I could take only one tour ever again, it would be this one. Our trip was ideal from start to finish. CW is blessed to have Alessandro and Manuela as guides—their passion for their culture and their ability to share it with others is incredible. Great food, great hikes, and a great education all around.

N. Jordan, Indiana, September 2011

Our tour of Tuscany & Umbria created wonderful memories for a lifetime! We felt that we had a real connection with the area and culture, and enjoyed the variety of walks!

J. Holland, North Carolina, May 2011

This trip was the trip of a lifetime for my husband and me. We celebrated our 30th wedding anniversary and it was the prefect way to celebrate!

G. & S. Heitsch, Illinois, October 2011

This was the best trip yet with CW. The kind and knowledgeable guides made all the difference.

D. Matthews, California, May 2012

I truly enjoy the CW approach to travel – walking through the country with guides who love to share the food, culture, art, history and folklore. Thanks for the memories…

M. Parker, California, October 2011

The Italy experience of a lifetime! Exceeded every expectation!

M. Schorn & R. Harvery, Kentucky, September 2011

Of the 18 CW tours that we have taken, this was the best designed and executed of all! Many options provided an experience tailored to various walking levels. Kudos to Manuela and Alex―great team work and joyous personalities.

R. & B. Wilking, Virginia, September 2011

Beautiful country, great food, great culture, knowledgeable guides, and wonderful companions.

A. Ulveland, Alberta, Canada, September 2011

I must say that our Tuscany & Umbria tour is a trip we will long remember―great location, pleasant lodging, and food to die for. We were so very fortunate to have had exceptional guides who evidenced a balanced combination of personality, enthusiasm, knowledge, and professionalism. Our fellow “walkers” added much to our experience as well.

E. & T. Hollahan, New York, September 2012

My husband and I loved just about everything on this tour. Our guide, Manuela, was fun, an expert in the area we were traveling in, organized, interesting, and experienced. We loved the walks, both the country hikes and the city walks. We absolutely loved the cuisine, and Manuela did a great job of picking out wonderful restaurants and menus that would let us experience a variety of Tuscan and Umbrian specials. Our group of 7 travelers really bonded and made it a fun experience for all. I can't wait to do another CW tour.

J. Kuzmeskus, Massachusetts, September 2012

The spots were beautiful and the guides made the experience of them richer than I could have expected. Their knowledge and passion for what they share with the walkers is a treasure.