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 historical 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 its 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 town’s main cathedral, to view its striking marble façade.

Later, you transfer to San Quirico d’Orcia, one of the pilgrimage routes that connected northern Europe to Rome, and your home for the next three nights. An important stop during medieval times along the Via Francigena, 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. A warm, wood-beamed restaurant in the heart of town welcomes you to dinner. Here, a glass of Brunello paired with a bistecca fiorentina (local grilled beef) is the perfect start to the week’s culinary delights.

Accommodation: Villa del Capitano, San Quirico d’Orcia
Included Meals: Breakfast, Lunch, Dinner

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

Today’s exploration begins on 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. The village’s restructuring came to a halt following Pius II’s death, and the only part of the urban plan that had been completed was the town center, Piazza Pio II. Here, the main monuments lie harmoniously along the town’s central axis, with the town hall opposite a 15th-century cathedral.

An optional afternoon walk departs from the tiny spa village of Bagno Vignoni, where you can soak your feet in the warm waters flowing out of the town’s picturesque main square. This pool is 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
Included Meals: Breakfast, Lunch, Dinner

4-7 miles, easy to moderate

Today you depart San Quirico for a short drive to the tailhead for a walk through gentle hills in the shade of old-growth woods, skirting vineyards where the famous Sangiovese Grosso grape is grown for Brunello wine. You might stop to visit an ancient Etruscan settlement, still under excavation. Then continue through farmland, ancient dwellings, wineries, and olive groves before making the dramatic descent to the isolated Romanesque Abbey of Sant’Antimo.

After a truly authentic lunch of pink risotto and wild boar stew at one of our favorite trattorias, you return to San Quirico. You have an independent afternoon of exploring or relaxing (or perhaps indulging in a spa treatment at your hotel’s nearby sister property). You may want to step out for a pre-dinner stroll and a visit to the Horti Leonini—a wonderful example of classic Italian-style gardens, built by Diomede Leoni in 1540. This evening, enjoy dinner on your own, with restaurant recommendations from your guides.

Accommodation: Villa del Capitano, San Quirico d’Orcia
Included Meals: Breakfast, Lunch

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

This morning you bid farewell to southern Tuscany as your drive winds through the rolling hills and medieval hilltop villages of the Crete Senesi, descends on the plains surrounding Lake Trasimeno, and enters the central valley of Umbria, a region known as the “Green Heart of Italy.”

Your 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. The intriguing history of Assisi’s city center and the Basilica of St. Francis come to life with interpretation from your guide. Afterward, enjoy lunch at a local restaurant.

The afternoon offers several options. You may transfer to Spello, your home for the next three nights, to stroll its picturesque alleys or relax by the hotel pool. Alternatively, an easy walking option is offered—leading 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
Included Meals: Breakfast, Lunch, Dinner

5-7 miles, easy to moderate

After breakfast, depart for Gubbio, the medieval masterpiece of Umbria that 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 endpoint 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, then meanders 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 descending into 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; many restaurant and trattoria menus offer chickpea soup drizzled with olive oil, bruschetta, or strangozzi, the regional square-shaped ribbon pasta (literally shoestring-like).

Accommodation: Hotel La Bastiglia, Spello
Included Meals: Breakfast, Lunch

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 as they 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 descend on foot, continuing through olive groves and alongside an ancient Roman aqueduct. This aqueduct once brought drinking water into town along the eastern side of the mountain.

This evening’s farewell dinner is at an extraordinary venue in Assisi: a restaurant built on top of a glassed-in site of remarkable Roman ruins. You dine on the finest local cuisine and toast your week’s adventures with a glass from the restaurant’s world-class wine cellar.

Accommodation: Hotel La Bastiglia, Spello
Included Meals: Breakfast, Lunch, Dinner

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 including recommendations on what to see and do in Rome during your stay.

Accommodation: Hotel dei Mellini, Rome
Included Meals: Breakfast

City tour of Siena; 2 hours, easy

After enjoying an included breakfast at your hotel your guides meet you at 9:30 a.m. in the lobby of Hotel de la Ville in Florence. They’ll be wearing Country Walkers shirts. Please be dressed for city walking. Comfortable walking shoes required. (Sneakers are acceptable.)

After meeting in Florence, you travel to Siena. The week begins with a walking tour of the historical 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 its 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 town’s main cathedral, to view its striking marble façade.

Later, you drive to San Quirico d’Orcia, one of the pilgrimage routes that connected northern Europe to Rome, and your home for the next three nights. An important stop during medieval times along the Via Francigena, 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. A warm, wood-beamed restaurant in the heart of town welcomes you to dinner. Here, a glass of Brunello paired, perhaps, with a bistecca fiorentina (local grilled beef) is the perfect start to the week’s culinary delights.

Accommodation: Villa del Capitano, San Quirico d’Orcia
Included Meals: Breakfast, Lunch, Dinner

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

Today’s exploration begins on 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. The village’s restructuring came to a halt following Pius II’s death, and the only part of the urban plan that had been completed was the town center, Piazza Pio II. Here, the main monuments lie harmoniously along the town’s central axis, with the town hall opposite a 15th-century cathedral.

An optional afternoon walk departs from the tiny spa village of Bagno Vignoni, where you can soak your feet in the warm waters flowing out of the town’s picturesque main square. This pool is 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 enjoying dinner on your own at one of the fine local eateries in town, with recommendations from your guides.

Accommodation: Villa del Capitano, San Quirico d’Orcia
Included Meals: Breakfast, Lunch

4-7 miles, easy to moderate

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

You continue on to the attractive hilltop town of Montalcino, where you have time to stop into one (or more!) of the town’s enoteche (wine bars) or restaurants, for a tasting and lunch on your own. Stroll through town, perhaps shopping for local products, perusing galleries, or snapping photos from the ramparts of the Rocca (the 14th century fortress that affords views towards Monte Amiata, Siena, and the hills of Maremma), before a mid-afternoon return to San Quirico. You have time to explore or relax (or perhaps indulge in a spa treatment at your hotel’s nearby sister property) before gathering for dinner. You may want to step out for a pre-dinner stroll and a visit to the Horti Leonini—a wonderful example of classic Italian-style gardens, built by Diomede Leoni in 1540. This evening, reunite with your guides and fellow travelers for a casual meal at a local osteria.

Accommodation: Villa del Capitano, San Quirico d’Orcia
Included Meals: Breakfast, Dinner

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

This morning you bid farewell to southern Tuscany as your drive winds through the rolling hills and medieval hilltop villages of the Crete Senesi, descends on the plains surrounding Lake Trasimeno, and enters the central valley of Umbria, a region known as the “Green Heart of Italy.”

Your 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. The intriguing history of Assisi’s city center and the Basilica of St. Francis come to life with interpretation from your guide. Afterward, enjoy lunch at a local restaurant.

The afternoon offers several options. You may travel to Spello, your home for the next three nights, to stroll its picturesque alleys or relax by the hotel pool or in the hammam (Turkish bath). Alternatively, an easy walking option is offered—leading out of Assisi into the lush, surrounding countryside and olive groves all the way back to Spello. Enjoy an independent dinner this evening at your hotel’s restaurant or at one of the charming trattorias in town. (Your guides will provide recommendations.)

Accommodation: Hotel La Bastiglia, Spello
Included Meals: Breakfast, Lunch

5-7 miles, easy to moderate

After breakfast, depart for Gubbio, the medieval masterpiece of Umbria that 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 endpoint 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, then meanders 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 descending into town, where you are free to explore (and refuel!) savoring lunch at an osteria of your choosing. 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; many restaurant and trattoria menus offer typical dishes such as chickpea soup drizzled with olive oil, bruschetta, or strangozzi, the regional square-shaped ribbon pasta (literally shoestring-like).

Accommodation: Hotel La Bastiglia, Spello
Included Meals: Breakfast

5-9 miles, easy to moderate

After breakfast, you embark on a short drive 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 as they 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 descend on foot, continuing through olive groves and alongside an ancient Roman aqueduct. This aqueduct once brought drinking water into town along the eastern side of the mountain.

This evening’s farewell dinner is at an extraordinary venue in Assisi: a restaurant built on top of a glassed-in site of remarkable Roman ruins. You dine on the finest local cuisine and toast your week’s adventures with a glass from the restaurant’s world-class wine cellar.

Accommodation: Hotel La Bastiglia, Spello
Included Meals: Breakfast, Lunch, Dinner

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.

The rest of the day is yours to enjoy at your leisure—perhaps explore the city, rest up in the hotel, or select a local restaurant for lunch and dinner. We provide detailed city information to help you plan your day.

Accommodation: Hotel dei Mellini, Rome
Included Meals: Breakfast

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 historical 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 its 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 town’s main cathedral, to view its striking marble façade.

Later, you transfer to San Quirico d’Orcia, one of the pilgrimage routes that connected northern Europe to Rome, and your home for the next three nights. An important stop during medieval times along the Via Francigena, 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. A warm, wood-beamed restaurant in the heart of town welcomes you to dinner. Here, a glass of Brunello paired with a bistecca fiorentina (local grilled beef) is the perfect start to the week’s culinary delights.

Accommodation: Villa del Capitano, San Quirico d’Orcia
Included Meals: Lunch, Dinner

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

Today’s exploration begins on 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. The village’s restructuring came to a halt following Pius II’s death, and the only part of the urban plan that had been completed was the town center, Piazza Pio II. Here, the main monuments lie harmoniously along the town’s central axis, with the town hall opposite a 15th-century cathedral.

An optional afternoon walk departs from the tiny spa village of Bagno Vignoni, where you can soak your feet in the warm waters flowing out of the town’s picturesque main square. This pool is 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
Included Meals: Breakfast, Lunch, Dinner

4-7 miles, easy to moderate

Today you depart San Quirico for a short drive to the tailhead for a walk through gentle hills in the shade of old-growth woods, skirting vineyards where the famous Sangiovese Grosso grape is grown for Brunello wine. You might stop to visit an ancient Etruscan settlement, still under excavation. Then continue through farmland, ancient dwellings, wineries, and olive groves before making the dramatic descent to the isolated Romanesque Abbey of Sant’Antimo.

After a truly authentic lunch of pink risotto and wild boar stew at one of our favorite trattorias, you return to San Quirico. You have an independent afternoon of exploring or relaxing (or perhaps indulging in a spa treatment at your hotel’s nearby sister property). You may want to step out for a pre-dinner stroll and a visit to the Horti Leonini—a wonderful example of classic Italian-style gardens, built by Diomede Leoni in 1540. This evening, enjoy dinner on your own, with restaurant recommendations from your guides.

Accommodation: Villa del Capitano, San Quirico d’Orcia
Included Meals: Breakfast, Lunch

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

This morning you bid farewell to southern Tuscany as your drive winds through the rolling hills and medieval hilltop villages of the Crete Senesi, descends on the plains surrounding Lake Trasimeno, and enters the central valley of Umbria, a region known as the “Green Heart of Italy.”

Your 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. The intriguing history of Assisi’s city center and the Basilica of St. Francis come to life with interpretation from your guide. Afterward, enjoy lunch at a local restaurant.

The afternoon offers several options. You may transfer to Spello, your home for the next three nights, to stroll its picturesque alleys or relax by the hotel pool. Alternatively, an easy walking option is offered—leading 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
Included Meals: Breakfast, Lunch, Dinner

5-7 miles, easy to moderate

After breakfast, depart for Gubbio, the medieval masterpiece of Umbria that 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 endpoint 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, then meanders 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 descending into 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; many restaurant and trattoria menus offer chickpea soup drizzled with olive oil, bruschetta, or strangozzi, the regional square-shaped ribbon pasta (literally shoestring-like).

Accommodation: Hotel La Bastiglia, Spello
Included Meals: Breakfast, Lunch

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 as they 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 descend on foot, continuing through olive groves and alongside an ancient Roman aqueduct. This aqueduct once brought drinking water into town along the eastern side of the mountain.

This evening’s farewell dinner is at an extraordinary venue in Assisi: a restaurant built on top of a glassed-in site of remarkable Roman ruins. You dine on the finest local cuisine and toast your week’s adventures with a glass from the restaurant’s world-class wine cellar.

Accommodation: Hotel La Bastiglia, Spello
Included Meals: Breakfast, Lunch, Dinner

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 in this stunning city, a former strategic Roman colony.. 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.

Included Meals: Breakfast

2 hours, easy walking tour of Siena

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

After meeting in Florence, you travel to Siena. The week begins with a walking tour of the historical 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 its 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 town’s main cathedral, to view its striking marble façade.

Later, you drive to San Quirico d’Orcia, one of the pilgrimage routes that connected northern Europe to Rome, and your home for the next three nights. An important stop during medieval times along the Via Francigena, 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. A warm, wood-beamed restaurant in the heart of town welcomes you to dinner. Here, a glass of Brunello paired, perhaps, with a bistecca fiorentina (local grilled beef) is the perfect start to the week’s culinary delights.

Accommodation: Villa del Capitano, San Quirico d’Orcia
Included Meals: Lunch, Dinner

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

Today’s exploration begins on 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. The village’s restructuring came to a halt following Pius II’s death, and the only part of the urban plan that had been completed was the town center, Piazza Pio II. Here, the main monuments lie harmoniously along the town’s central axis, with the town hall opposite a 15th-century cathedral.

An optional afternoon walk departs from the tiny spa village of Bagno Vignoni, where you can soak your feet in the warm waters flowing out of the town’s picturesque main square. This pool is 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 enjoying dinner on your own at one of the fine local eateries in town, with recommendations from your guides.

Accommodation: Villa del Capitano, San Quirico d’Orcia
Included Meals: Breakfast, Lunch

4-7 miles, easy to moderate

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

You continue on to the attractive hilltop town of Montalcino, where you have time to stop into one (or more!) of the town’s enoteche (wine bars) or restaurants, for a tasting and lunch on your own. Stroll through town, perhaps shopping for local products, perusing galleries, or snapping photos from the ramparts of the Rocca (the 14th century fortress that affords views towards Monte Amiata, Siena, and the hills of Maremma), before a mid-afternoon return to San Quirico. You have time to explore or relax (or perhaps indulge in a spa treatment at your hotel’s nearby sister property) before gathering for dinner. You may want to step out for a pre-dinner stroll and a visit to the Horti Leonini—a wonderful example of classic Italian-style gardens, built by Diomede Leoni in 1540. This evening, reunite with your guides and fellow travelers for a casual meal at a local osteria.

Accommodation: Villa del Capitano, San Quirico d’Orcia
Included Meals: Breakfast, Dinner

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

This morning you bid farewell to southern Tuscany as your drive winds through the rolling hills and medieval hilltop villages of the Crete Senesi, descends on the plains surrounding Lake Trasimeno, and enters the central valley of Umbria, a region known as the “Green Heart of Italy.”

Your 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. The intriguing history of Assisi’s city center and the Basilica of St. Francis come to life with interpretation from your guide. Afterward, enjoy lunch at a local restaurant.

The afternoon offers several options. You may travel to Spello, your home for the next three nights, to stroll its picturesque alleys or relax by the hotel pool or in the hammam (Turkish bath). Alternatively, an easy walking option is offered—leading out of Assisi into the lush, surrounding countryside and olive groves all the way back to Spello. Enjoy an independent dinner this evening at your hotel’s restaurant or at one of the charming trattorias in town. (Your guides will provide recommendations.)

Accommodation: Hotel La Bastiglia, Spello
Included Meals: Breakfast, Lunch

5-7 miles, easy to moderate

After breakfast, depart for Gubbio, the medieval masterpiece of Umbria that 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 endpoint 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, then meanders 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 descending into town, where you are free to explore (and refuel!) savoring lunch at an osteria of your choosing. 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; many restaurant and trattoria menus offer typical dishes such as chickpea soup drizzled with olive oil, bruschetta, or strangozzi, the regional square-shaped ribbon pasta (literally shoestring-like).

Accommodation: Hotel La Bastiglia, Spello
Included Meals: Breakfast

5-9 miles, easy to moderate

After breakfast, you embark on a short drive 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 as they 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 descend on foot, continuing through olive groves and alongside an ancient Roman aqueduct. This aqueduct once brought drinking water into town along the eastern side of the mountain.

This evening’s farewell dinner is at an extraordinary venue in Assisi: a restaurant built on top of a glassed-in site of remarkable Roman ruins. You dine on the finest local cuisine and toast your week’s adventures with a glass from the restaurant’s world-class wine cellar.

Accommodation: Hotel La Bastiglia, Spello
Included Meals: Breakfast, Lunch, Dinner

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.