Italy: Tuscany & Umbria

City tour of Siena; 2 hours, easy

Breakfast is included at your hotel. Your guide(s) meet you at 9:30 a.m. in the lobby of Hotel de la Ville, Piazza Antinori, 1, Florence. Your guide(s) will be wearing a Country Walkers shirt. Please be dressed for city walking. Comfortable walking shoes required. (Sneakers are acceptable.)

After meeting in Florence, you transfer to Siena. The week begins with a walking tour of the historic center of Siena, an 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 Piazza del Campo, 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 facade.

Later, you transfer to San Quirico d’Orcia, and your home for the next two nights. An important stop during medieval times along the Via Francigena—one of the pilgrimage routes that connected northern Europe to Rome—San Quirico is a charming, walled, hilltop town surrounded by vineyards that produce three great Tuscan wines: Montepulciano, Brunello, and the Orcia DOC. Magnificent medieval architecture adorns its streets, and your boutique hotel is located just outside one of the town gates. 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 bistecca fiorentina (local grilled beef), a perfect start to the week’s culinary delights.

Accommodation: Villa del Capitano, San Quirico d’Orcia

6 miles, easy to moderate; optional 2-3 miles, easy to moderate

Today’s exploration begins in the outskirts of San Quirico. After an initial short drive to the village of Torrenieri, step onto a dirt lane that 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, and homemade preserves and pickles, accompanied by their house wine. After 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. Here, 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 San Quirico, you have time to relax before another delicious dinner featuring local specialties.

Accommodation: Villa del Capitano, San Quirico d’Orcia

4-7 miles, easy to moderate

Today you depart San Quirico to 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.

Accommodation: Hotel La Bastiglia, Spello

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. After visiting the church and admiring the three ceri contained within, enjoy a scenic funicular ride down to town where a lunch of regional specialties awaits. After lunch, you return to Spello, with an optional walk en route that traces ancient oak-lined farm roads leading all the way to the hotel. 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 ribbon pasta (literally shoestring-like).

Accommodation: Hotel La Bastiglia, Spello

3 miles, easy; 3-4 miles, easy to moderate

The morning is 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 interpretation from your guide. Afterward, enjoy lunch at a local restaurant.

The afternoon offers several options. You may return to Spello to stroll its picturesque alleys or to relax by the hotel pool. Alternatively, an easy walking option is offered—this time, venturing out of Assisi 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.

Accommodation: Hotel La Bastiglia, Spello

5-9 miles, easy to moderate

After breakfast, you embark on 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 a very special venue in Assisi: a restaurant built on top of a glassed-in site of remarkable Roman ruins. You dine on the finest Umbrian cuisine and toast your week’s adventures with a glass from the world-class wine cellar.

Accommodation: Hotel La Bastiglia, Spello

After enjoying a leisurely breakfast in Spello and traveling with your group to Rome, a small-group transfer brings you to the Hotel Dei Mellini for your post-tour night. (Lunch and dinner are on your own.)

After a leisurely breakfast, you depart Spello for Rome. Time and weather permitting, a brief stop en route in the walled medieval hill town of Spoleto may allow for a walk and view from the impressive Ponte delle Torri (Tower Bridge). You arrive early afternoon to Rome for your post-tour night. (Lunch and dinner are on your own.)

Country Walkers provides City Information containing recommendations about what to see and do in Rome during your stay.

Accommodation: Hotel Dei Mellini, Rome

City tour of Siena; 2 hours, easy

Your guide(s) meet you at 9:30 a.m. in the lobby of Hotel de la Ville, Piazza Antinori, 1, Florence. Your guide(s) will be wearing a Country Walkers shirt. Please be dressed for city walking. Comfortable walking shoes required. (Sneakers are acceptable.)

After meeting in Florence, you transfer to Siena. The week begins with a walking tour of the historic center of Siena, an 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 Piazza del Campo, 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 facade.

Later, you transfer to San Quirico d’Orcia, and your home for the next two nights. An important stop during medieval times along the Via Francigena—one of the pilgrimage routes that connected northern Europe to Rome—San Quirico is a charming, walled, hilltop town surrounded by vineyards that produce three great Tuscan wines: Montepulciano, Brunello, and the Orcia DOC. Magnificent medieval architecture adorns its streets, and your boutique hotel is located just outside one of the town gates. 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 bistecca fiorentina (local grilled beef), a perfect start to the week’s culinary delights.

Accommodation: Villa del Capitano, San Quirico d’Orcia

6 miles, easy to moderate; optional 2-3 miles, easy to moderate

Today’s exploration begins in the outskirts of San Quirico. After an initial short drive to the village of Torrenieri, step onto a dirt lane that 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, and homemade preserves and pickles, accompanied by their house wine. After 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. Here, 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 San Quirico, you have time to relax before another delicious dinner featuring local specialties.

Accommodation: Villa del Capitano, San Quirico d’Orcia

4-7 miles, easy to moderate

Today you depart San Quirico to 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.

Accommodation: Hotel La Bastiglia, Spello

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. After visiting the church and admiring the three ceri contained within, enjoy a scenic funicular ride down to town where a lunch of regional specialties awaits. After lunch, you return to Spello, with an optional walk en route that traces ancient oak-lined farm roads leading all the way to the hotel. 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 ribbon pasta (literally shoestring-like).

Accommodation: Hotel La Bastiglia, Spello

3 miles, easy; 3-4 miles, easy to moderate

The morning is 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 interpretation from your guide. Afterward, enjoy lunch at a local restaurant.

The afternoon offers several options. You may return to Spello to stroll its picturesque alleys or to relax by the hotel pool. Alternatively, an easy walking option is offered—this time, venturing out of Assisi 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.

Accommodation: Hotel La Bastiglia, Spello

5-9 miles, easy to moderate

After breakfast, you embark on 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 a very special venue in Assisi: a restaurant built on top of a glassed-in site of remarkable Roman ruins. You dine on the finest Umbrian cuisine and toast your week’s adventures with a glass from the world-class wine cellar.

Accommodation: Hotel La Bastiglia, Spello

Ciao! Enjoy a leisurely breakfast and final guided excursion before your Umbria and Tuscany walking tour comes to an end. Bid farewell to your guides in Rome, staying on to explore more, or departing for onward travels.

This morning, enjoy a final guided walking excursion through magnificent Spoleto before continuing on to Rome.

After a leisurely breakfast, you depart Spello for Rome. Time and weather permitting, a brief stop en route in the walled medieval hill town of Spoleto may allow for a walk and view from the impressive Ponte delle Torri (Tower Bridge). You arrive at Roma Termini (Rome’s central train station) at approximately 1:30 p.m. Here, you bid farewell to your guides and make connections for onward travels.