DAY 1

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 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

DAY 2

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 toward Pienza, the morning’s destination. Along a ridge between the Orcia Valley and the Crete Senesi (Sienese hills), you pay a visit to the 15th-century convent of Sant’Anna in Camprena, a breath-taking former Olivetan Benedictine monastery where “The English Patient” was filmed.

Lunch awaits at an old Tuscan farm house, where your hosts welcome you with an assortment of local pecorino (sheep 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 being driven to dinner overlooking the plains on the outskirts of town.
Hotel Dei Capitani, Montalcino

DAY 3

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, historic property featuring a panoramic outdoor terrace and swimming pool—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 al fresco on the terrace of your hotel.
Hotel La Bastiglia, Spello

DAY 4

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 the hotel and relax by the pool, or stroll the picturesque alleys of Spello. 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 the fruit of your labor in an optional hands-on cooking class! You join Chef Marco Gubbiotti in the kitchen and help him prepare regional dishes while learning some of the many culinary traditions of the region.
Hotel La Bastiglia, Spello

DAY 5

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 historic 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―perhaps suckling pig roasted over an open fire.

After lunch you are free to wander around the historic 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

DAY 6

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 table is waiting and 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 all the way 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 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

DAY 7

You depart Spello for the picturesque city of Orvieto, situated atop a tufo (compacted volcanic ashes) outcrop. 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 Changes

Please 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.

Nights 1 & 2

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.

Nights 3, 4, 5 & 6

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.

Please note that this is a sample hotel itinerary for this tour. While these exact hotels are featured on most departures, we occasionally reserve other hotels of similar style and quality. If you are currently booked on a Country Walkers adventure, a hotel 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 hotels selected for any of our tours.

Alex Gullo

Alessandro 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. 

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.