Italy: Tuscany & Umbria

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

Italy

Tuscany & Umbria

overview

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 a parade of specialty dishes creates 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…and admire the magnificent art museum in Gubbio’s 14th-century Palazzo dei Consoli. The summit of Mt. Subasio presents splendid views and one of the finest walks in all of Italy. In the lush valleys of Tuscany and Umbria, historic chapels sit in charming seclusion among grapevines and olive trees. From fresco master­pieces and Roman aqueducts to Etruscan ruins and historic abbeys, you’ll enjoy a grand buffet of Italian culture along with tastings of cheeses, olive oils, truffles, wines, and other local delicacies that fill every day with unique flavor.

2014 Downloadable Itinerary

2015 Downloadable Itinerary

Activity Level
Easy to moderate;
4-8 miles daily
Meet
Florence, Italy
Depart
Orvieto, Italy
Reading List
Recommended
pre-trip reading
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From our blog

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 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
 

Call 800.234.6900 to book this trip.

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

Call 800.234.6900 to book this trip.

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Itinerary and Accommodations

Days
Destination
1
Montalcino
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2
Montalcino
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3
Spello
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4
Spello
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5
Spello
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6
Spello
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7
Spello
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Day 1

Montalcino

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

Montalcino

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

Spello

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 17th-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 Palazzo Bocci

Spello, Italy

Centrally located within the medieval walls of Spello, the Hotel Palazzo Bocci is situated in an elegant townhouse dating to the 17th century. Enveloped in history, tradition, and art, the palazzo features important works of art, spacious and well-appointed guest rooms, and lovely common areas, including a frescoed reading lounge, bar, and outdoor terrace.

Day 4

Spello

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 Palazzo Bocci

Spello, Italy

Centrally located within the medieval walls of Spello, the Hotel Palazzo Bocci is situated in an elegant townhouse dating to the 17th century. Enveloped in history, tradition, and art, the palazzo features important works of art, spacious and well-appointed guest rooms, and lovely common areas, including a frescoed reading lounge, bar, and outdoor terrace.

Day 5

Spello

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 Palazzo Bocci

Spello, Italy

Centrally located within the medieval walls of Spello, the Hotel Palazzo Bocci is situated in an elegant townhouse dating to the 17th century. Enveloped in history, tradition, and art, the palazzo features important works of art, spacious and well-appointed guest rooms, and lovely common areas, including a frescoed reading lounge, bar, and outdoor terrace.

Day 6

Spello

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 Palazzo Bocci

Spello, Italy

Centrally located within the medieval walls of Spello, the Hotel Palazzo Bocci is situated in an elegant townhouse dating to the 17th century. Enveloped in history, tradition, and art, the palazzo features important works of art, spacious and well-appointed guest rooms, and lovely common areas, including a frescoed reading lounge, bar, and outdoor terrace.

Day 7

Spello

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 CW adventure, an itinerary has been sent to you for your exact departure date. Please call CW at 800.464.9255 if you have any questions about the exact itinerary or hotels selected for any of our tours.

Guides

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

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.

M. Frankel, New York, May 2013

One of, if not the, best I have been on with CW. Walking through the Italian countryside with outstanding guides and an outstanding group of fellow walkers, plus food, wine, and wildflowers!

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.  

V. Trentman, Ohio, May 2011

I would recommend this tour to anyone who wants to experience Tuscany and Umbria―it was fabulous! Everything was top-notch―the hikes, the food, the fun, our group. Alessandro and Manuela are the BEST!

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.

F. Simone, Pennsylvania, May 2012

Alex is an excellent guide; his knowledge of art and history makes the tour more interesting. Great food and wine. A nice mix of art, history and the Italian countryside

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. McKittrick, Maine, October 2012

I saw beautiful country, art and architecture, met interesting, entertaining and friendly people (Italian and American) and ate and drank wonderful food and wine.

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.

S. Blease, New York, May 2011

Best vacation ever―we were celebrating our 30th wedding anniversary and the whole experience was memorable.

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.

T. Gehrels, Ontario, Canada, October 2011

Best guides I ever experienced―unrivalled knowledge and contagious enthusiasm.

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!

D. Hofer, California, September 2011

This was a wonderful experience and a perfect trip to experience Italy and CW for the first time. Both Italy’s beauty and CW’s tour and guides were beyond expectations.

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

This was the trip of a lifetime! It far exceeded my expectations in every way…gourmet food and wine, accommodations tour guides, unique local culture and historical information―simply incredible!

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. Scott, California, May 2011

Fabulous! Food was divine, guides were knowledgeable and helpful. Beautiful countryside.

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.

J. Troia, Wisconsin, September 2011

The walks were spectacular among vineyards, olive groves, up and down hills, and seeing fabulous small towns along the way. The food and wine were super and guides were great once again!

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.

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