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.

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 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 farmhouse, 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 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.

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 al fresco on the terrace of your hotel.

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 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 at an intimate restaurant, where you are welcomed with a glass of crisp prosecco on a panoramic terrace overlooking the Umbrian plain.

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 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.

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.

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 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 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 adventure with a glass from the world-class wine cellar.

Easy city walking tour of Orvieto. Departure

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.