Italy: Tuscany & Umbria

Your vacation is about to begin! Spend your first night aloft and arrive ready for an unforgettable trip.

Start off your first day in Florence right by having a Country Walkers representative greet you at the airport. A complimentary car service will whisk you to your centrally located hotel. From here, you are perfectly positioned to explore this charming city at your leisure.

City Tour of Siena; 2-2.5 hours, (approximately 3 miles), easy

After enjoying an included breakfast at your hotel, your leaders will meet you at 9:00 a.m. in the lobby of the 25hours Hotel Florence. They’ll be wearing Country Walkers shirts for easy identification. Please be dressed for city walking—comfortable walking shoes are required (sneakers are acceptable).

After meeting in Florence, you’ll travel to Siena, where your week begins with a walking tour of the historic city center. Set dramatically across three hills, Siena is a stunning blend of Gothic and Romanesque architecture and rivals Florence in both beauty and cultural significance. Following a light lunch of local Sienese specialties, you’ll explore the iconic Piazza del Campo, dominated by its grand town hall and towering campanile. This remarkable square is famously the setting for the Palio, Siena’s celebrated horse race. Your engaging local guide will also lead you to the magnificent Duomo, the town’s cathedral, known for its striking black-and-white marble façade.

Later, you’ll drive to San Quirico d’Orcia, located along the historic Via Francigena, a pilgrimage route that once connected northern Europe to Rome. This charming walled hilltop town will be your home for the next three nights. Surrounded by vineyards producing Tuscany’s finest wines—Montepulciano, Brunello, and Orcia DOC—San Quirico is rich in medieval architecture and timeless charm. Your boutique hotel is just outside one of the town gates, offering easy access to the village.

In the evening, gather for dinner in a warm, wood-beamed restaurant in the heart of town. A glass of Brunello paired with a local specialty like bistecca fiorentina (Tuscan grilled beef) is the perfect way to begin your week of culinary delights.

Included Meals: Breakfast, Lunch, Dinner

7 miles, easy to moderate, 550-ft. elevation gain; optional 3-3.5 miles, easy to moderate (with challenging sections), 750-ft. elevation gain

Today’s exploration begins on the outskirts of San Quirico. After a short drive to the village of Torrenieri, you’ll set out on a quiet gravel road that gently winds through rolling terrain between the Orcia Valley and the Crete Senesi (Sienese hills), heading toward Pienza, your morning destination. This spectacular walk offers postcard-worthy views of hill towns and countryside villas, framed by cypress and walnut trees. In spring, the landscape comes alive with blooming wildflowers.

Lunch is served at a rustic Tuscan farmhouse, where your hosts welcome you with an assortment of local pecorino (sheep’s milk cheese), cold cuts, fresh salads, frittatas, and pickled vegetables, all accompanied by house wine and locally produced olive oil.

After lunch, a short drive brings you to Pienza, birthplace of Enea Silvio Piccolomini, who became Pope Pius II in 1458. With a vision of creating the “ideal Renaissance town,” Pius II commissioned Florentine architect Bernardo Rossellino to redesign the village. Though construction halted upon the Pope’s death, the completed town center—Piazza Pio II—remains a striking example of Renaissance urban planning. Its main monuments are harmoniously aligned along a central axis, with the town hall directly facing the 15th-century cathedral.

In the afternoon, an optional walk departs from the tiny spa village of Bagno Vignoni. The route begins with a steady 45-minute climb over a trail of loose rock and gravel, transitioning to gravel road and finally paved surfaces. It ends in a small hamlet with lovely views over the valley below.

Upon returning to the hotel in San Quirico, take time to relax before heading out to enjoy dinner on your own at one of the town’s excellent local eateries—your leaders will provide recommendations.

Included Meals: Breakfast, Lunch

4-7 miles, easy to moderate

Today, you depart San Quirico and walk through gentle hills shaded by old-growth woods, skirting vineyards where the renowned Sangiovese Grosso grape is cultivated for world-famous Brunello di Montalcino wine. Along the way, you may pause to visit an ancient Etruscan settlement, still under excavation. The trail continues through farmland, historic dwellings, wineries, and olive groves before making a dramatic descent to the secluded Romanesque Abbey of Sant’Antimo.

From here, you continue on to the charming hilltop town of Montalcino, where you’ll have time for lunch on your own at one of the town’s inviting enoteche (wine bars) or restaurants. Enjoy a leisurely stroll through the town—perhaps browsing local shops, visiting art galleries, or capturing panoramic photos from the Rocca, a 14th-century fortress offering sweeping views of Monte Amiata, Siena, and the Maremma hills.

Later, visit our friend’s cantina (winery) to sample some of the acclaimed wines for which this region is celebrated. Afterwards, enjoy time to explore, relax, or even indulge in a spa treatment at your hotel’s nearby sister property.

Before dinner, you might take a peaceful stroll to the Horti Leonini, a beautiful example of classical Italian garden design, created by Diomede Leoni in 1540.

This evening, reunite with your leaders and fellow travelers for a casual, family-style meal at a local osteria. The menu may feature homemade ravioli, tagliata (grilled beef) with porcini mushrooms, and of course, a glass or two of local vino—a warm and delicious way to end the day.

Included Meals: Breakfast, Dinner

3 miles, easy; optional 3 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 across the plains surrounding Lake Trasimeno, and enters the central valley of Umbria—a region often called the Green Heart of Italy.

Your morning is devoted to a three-hour exploration of Assisi. Perched on the slopes of Mount Subasio, this stunning town has preserved its medieval charm and its deep connection to St. Francis. The captivating history of Assisi’s city center and the Basilica of St. Francis comes to life through the insights of your leader. After the tour, enjoy lunch on your own at a local restaurant, followed by time for independent exploration.

The afternoon offers a few options. You may travel directly to Spello, your home for the next three nights, to unwind—perhaps with a stroll through its flower-lined alleys, a relaxing dip in the hotel pool, or a visit to the hammam (Turkish bath). Alternatively, an easy and scenic walk from Assisi to Spello is available, leading through lush countryside and olive groves.

In the evening, gather for an included aperitivo at your hotel, followed by a delicious dinner of regional specialties served in the hotel’s restaurant.

Included Meals: Breakfast, Dinner

5-7 miles, easy to moderate (with challenging sections), 1,220-ft. elevation gain

After breakfast, depart for Gubbio, a medieval masterpiece in Umbria that enchants visitors with its narrow alleys and surprisingly spacious panoramic piazza, framed by the impressive Palazzo Comunale. Following a scenic drive, your morning walk leads to the Church of Saint Ubaldo, perched high on the mountainside overlooking the town. This church marks the endpoint of the annual Race of the Ceri, a vibrant historical festival during which locals race through the streets carrying massive wooden structures known as ceri, which resemble giant candlesticks.

The walking route passes limestone outcrops and a tiny chapel, then winds through forested paths, alongside a creek, and up a narrow gorge—with some challenging, rocky sections along the way.

After visiting the church and viewing the three ceremonial ceri housed inside, enjoy a scenic descent into Gubbio via funicular, where you’ll savor lunch at one of our favorite osterias.

After lunch, return to Spello, with the option to take a walk along ancient oak-lined farm roads that lead all the way back to your hotel. Your leaders will provide suggestions for dinner on your own in town. Many local restaurants and trattorias serve typical Umbrian dishes such as chickpea soup drizzled with olive oil, bruschetta, and strangozzi—a regional, square-shaped ribbon pasta (literally “little shoelaces”).

Included Meals: Breakfast, Lunch

5-7 miles, easy to moderate and optional 2.5 miles, easy to moderate

After breakfast, you’ll take a short drive to the Natural Park of Mount Subasio, a protected area with peaceful trails winding through open meadows and oak and pine forests. Mount Subasio is the expansive mountain on whose slopes Assisi was built. A place of subtle beauty and deep spiritual resonance, it is said that St. Francis once preached here to birds gathered on the branches.

While hiking along the summit meadows, you may encounter grazing sheep, white Chianina cattle, and semi-wild horses before descending about 445 feet to the small, charming hamlet of Collepino for lunch. A welcoming table awaits, laid with a generous antipasto of assorted bruschetta, followed by grilled meats and vegetables.

After lunch, you may choose to return to Spello by van or continue on foot, descending through the forest along a well-maintained trail. The path leads through olive groves and alongside an ancient Roman aqueduct, which once brought drinking water into town from the eastern slopes of the mountain.

This evening’s farewell dinner features another delicious, seasonal meal and the chance to raise a glass—drawn from the restaurant’s exceptional wine cellar—in a toast to your week’s adventures.

Included Meals: Breakfast, Lunch, Dinner

After a leisurely breakfast, you’ll depart Spello and travel to Rome, arriving at the River Palace Hotel at approximately 11:30 a.m. Upon arrival, your tour leaders will offer a brief 45-minute orientation walk to help you get acquainted with the area.

The rest of the day is yours to enjoy at your leisure—perhaps explore the city’s iconic sights, relax at the hotel, or choose a local restaurant for lunch and dinner. We’ll provide detailed city information to help you make the most of your time in Rome.

Included Meals: Breakfast

Ciao! After an included breakfast this morning, complimentary transportation will be provided to Rome’s Leonardo da Vinci Airport (Fiumicino), based on your departure time.

Included Meals: Breakfast

Your vacation is about to begin! Spend your first night aloft and arrive ready for an unforgettable trip.

Start off your first day in Florence right by having a Country Walkers representative greet you at the airport. A complimentary car service will whisk you to your centrally located hotel. From here, you are perfectly positioned to explore this charming city at your leisure.

City tour of Siena; 2-2.5 hours, (approximately 3 miles), easy

After enjoying an included breakfast at your hotel your leaders meet you at 9:00 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 are 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 in beauty and 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 leader takes 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 essential 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.

Included Meals: Breakfast, Lunch, Dinner

7 miles, easy to moderate, 550-ft. elevation gain; optional 3-3.5 miles, easy to moderate (with challenging sections), 750-ft. elevation gain

Today’s exploration begins on the outskirts of San Quirico. After an initial short drive to the village of Torrenieri, step onto a quiet gravel road that meanders along rolling terrain between the Orcia Valley and the Crete Senesi (Sienese hills) toward Pienza, the morning’s destination. This spectacular walk features postcard views of the hill towns and surrounding villas, dotted with cypress and walnut trees. In the spring, expect to see wildflowers in bloom.

Lunch awaits at an old Tuscan farmhouse, where your hosts welcome you with an assortment of local pecorino (sheep’s milk cheese), cold cuts, salads, frittatas, and pickled vegetables accompanied by their house wine and local olive oil. 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. Your route is marked by a long (45-minute) climb along a trail with loose rocks and gravel. It then transitions to gravel road and eventually pavement—culminating at a small hamlet with pretty views over the valley. Upon 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 leaders.

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-renowned 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 of the town’s enoteche (wine bars) or restaurants, for 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). Continue on to our friend’s cantina (or winery), and sample some of the wines for which this region is renowned. Afterward, 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 leaders and fellow travelers for a casual meal served family style, perhaps featuring homemade ravioli and a tagliata (grilled steak) with porcini mushrooms (accompanied by a glass or two of vino) at a local osteria.

Included Meals: Breakfast, Dinner

3 miles, easy; optional 3 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 a (three-hour) 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 leader. Afterward, enjoy lunch at a local restaurant of your choice, with time for independent exploration.

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, and beautiful, 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 leaders will provide recommendations.

Included Meals: Breakfast

5-7 miles, easy to moderate (with challenging sections), 1,220-ft. elevation gain

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 that includes some challenging rocky sections.

After visiting the church and admiring the three ceri contained within, enjoy a scenic funicular ride descending into town, where you savor lunch at one of our favorite osterias. 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 leaders 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).

Included Meals: Breakfast, Lunch

5-7 miles, easy to moderate and optional 2.5 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 (445 feet) 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 forest along a well-maintained trail and 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 feature’s another meal of delicious, seasonal cuisine and an opportunity to toast your week’s adventures with a glass from the restaurant’s outstanding wine cellar.

Included Meals: Breakfast, Lunch, Dinner

After a leisurely breakfast, you depart Spello for Rome. You arrive at Hotel dei Mellini at approximately 11:30 a.m. Your tour leaders provide a brief (45-minute) orientation walk on arrival.

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.

Included Meals: Breakfast

After an included breakfast this morning, complimentary transportation is provided to Rome’s Leonardo da Vinci Airport based on your departure time.

Included Meals: Breakfast

City tour of Siena; 2-2.5 hours (approximately 3 miles), easy

Your leaders will meet you at 9:00 a.m. in the lobby of the 25hours Hotel Florence. They’ll be wearing Country Walkers shirts for easy identification. Please be dressed for city walking—comfortable walking shoes are required (sneakers are acceptable).

After meeting in Florence, you’ll travel to Siena, where your week begins with a walking tour of the historic city center. Set dramatically across three hills, Siena is a stunning blend of Gothic and Romanesque architecture and rivals Florence in both beauty and cultural significance. Following a light lunch of local Sienese specialties, you’ll explore the iconic Piazza del Campo, dominated by its grand town hall and towering campanile. This remarkable square is famously the setting for the Palio, Siena’s celebrated horse race. Your engaging local guide will also lead you to the magnificent Duomo, the town’s cathedral, known for its striking black-and-white marble façade.

Later, you’ll drive to San Quirico d’Orcia, located along the historic Via Francigena, a pilgrimage route that once connected northern Europe to Rome. This charming walled hilltop town will be your home for the next three nights. Surrounded by vineyards producing Tuscany’s finest wines—Montepulciano, Brunello, and Orcia DOC—San Quirico is rich in medieval architecture and timeless charm. Your boutique hotel is just outside one of the town gates, offering easy access to the village.

In the evening, gather for dinner in a warm, wood-beamed restaurant in the heart of town. A glass of Brunello paired with a local specialty like bistecca fiorentina (Tuscan grilled beef) is the perfect way to begin your week of culinary delights.

Included Meals: Lunch, Dinner

7 miles, easy to moderate, 550-ft. elevation gain; optional 3-3.5 miles, easy to moderate (with challenging sections), 750-ft. elevation gain

Today’s exploration begins on the outskirts of San Quirico. After a short drive to the village of Torrenieri, you’ll set out on a quiet gravel road that gently winds through rolling terrain between the Orcia Valley and the Crete Senesi (Sienese hills), heading toward Pienza, your morning destination. This spectacular walk offers postcard-worthy views of hill towns and countryside villas, framed by cypress and walnut trees. In spring, the landscape comes alive with blooming wildflowers.

Lunch is served at a rustic Tuscan farmhouse, where your hosts welcome you with an assortment of local pecorino (sheep’s milk cheese), cold cuts, fresh salads, frittatas, and pickled vegetables, all accompanied by house wine and locally produced olive oil.

After lunch, a short drive brings you to Pienza, birthplace of Enea Silvio Piccolomini, who became Pope Pius II in 1458. With a vision of creating the “ideal Renaissance town,” Pius II commissioned Florentine architect Bernardo Rossellino to redesign the village. Though construction halted upon the Pope’s death, the completed town center—Piazza Pio II—remains a striking example of Renaissance urban planning. Its main monuments are harmoniously aligned along a central axis, with the town hall directly facing the 15th-century cathedral.

In the afternoon, an optional walk departs from the tiny spa village of Bagno Vignoni. The route begins with a steady 45-minute climb over a trail of loose rock and gravel, transitioning to gravel road and finally paved surfaces. It ends in a small hamlet with lovely views over the valley below.

Upon returning to the hotel in San Quirico, take time to relax before heading out to enjoy dinner on your own at one of the town’s excellent local eateries—your leaders will provide recommendations.

Included Meals: Breakfast, Lunch

4-7 miles, easy to moderate

Today, you depart San Quirico and walk through gentle hills shaded by old-growth woods, skirting vineyards where the renowned Sangiovese Grosso grape is cultivated for world-famous Brunello di Montalcino wine. Along the way, you may pause to visit an ancient Etruscan settlement, still under excavation. The trail continues through farmland, historic dwellings, wineries, and olive groves before making a dramatic descent to the secluded Romanesque Abbey of Sant’Antimo.

From here, you continue on to the charming hilltop town of Montalcino, where you’ll have time for lunch on your own at one of the town’s inviting enoteche (wine bars) or restaurants. Enjoy a leisurely stroll through the town—perhaps browsing local shops, visiting art galleries, or capturing panoramic photos from the Rocca, a 14th-century fortress offering sweeping views of Monte Amiata, Siena, and the Maremma hills.

Later, visit our friend’s cantina (winery) to sample some of the acclaimed wines for which this region is celebrated. Afterwards, enjoy time to explore, relax, or even indulge in a spa treatment at your hotel’s nearby sister property.

Before dinner, you might take a peaceful stroll to the Horti Leonini, a beautiful example of classical Italian garden design, created by Diomede Leoni in 1540.

This evening, reunite with your leaders and fellow travelers for a casual, family-style meal at a local osteria. The menu may feature homemade ravioli, tagliata (grilled beef) with porcini mushrooms, and of course, a glass or two of local vino—a warm and delicious way to end the day.

Included Meals: Breakfast, Dinner

3 miles, easy; optional 3 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 across the plains surrounding Lake Trasimeno, and enters the central valley of Umbria—a region often called the Green Heart of Italy.

Your morning is devoted to a three-hour exploration of Assisi. Perched on the slopes of Mount Subasio, this stunning town has preserved its medieval charm and its deep connection to St. Francis. The captivating history of Assisi’s city center and the Basilica of St. Francis comes to life through the insights of your leader. After the tour, enjoy lunch on your own at a local restaurant, followed by time for independent exploration.

The afternoon offers a few options. You may travel directly to Spello, your home for the next three nights, to unwind—perhaps with a stroll through its flower-lined alleys, a relaxing dip in the hotel pool, or a visit to the hammam (Turkish bath). Alternatively, an easy and scenic walk from Assisi to Spello is available, leading through lush countryside and olive groves.

In the evening, gather for an included aperitivo at your hotel, followed by a delicious dinner of regional specialties served in the hotel’s restaurant.

Included Meals: Breakfast, Dinner

5-7 miles, easy to moderate (with challenging sections), 1,220-ft. elevation gain

After breakfast, depart for Gubbio, a medieval masterpiece in Umbria that enchants visitors with its narrow alleys and surprisingly spacious panoramic piazza, framed by the impressive Palazzo Comunale. Following a scenic drive, your morning walk leads to the Church of Saint Ubaldo, perched high on the mountainside overlooking the town. This church marks the endpoint of the annual Race of the Ceri, a vibrant historical festival during which locals race through the streets carrying massive wooden structures known as ceri, which resemble giant candlesticks.

The walking route passes limestone outcrops and a tiny chapel, then winds through forested paths, alongside a creek, and up a narrow gorge—with some challenging, rocky sections along the way.

After visiting the church and viewing the three ceremonial ceri housed inside, enjoy a scenic descent into Gubbio via funicular, where you’ll savor lunch at one of our favorite osterias.

After lunch, return to Spello, with the option to take a walk along ancient oak-lined farm roads that lead all the way back to your hotel. Your leaders will provide suggestions for dinner on your own in town. Many local restaurants and trattorias serve typical Umbrian dishes such as chickpea soup drizzled with olive oil, bruschetta, and strangozzi—a regional, square-shaped ribbon pasta (literally “little shoelaces”).

Included Meals: Breakfast, Lunch

5-7 miles, easy to moderate and optional 2.5 miles, easy to moderate

After breakfast, you’ll take a short drive to the Natural Park of Mount Subasio, a protected area with peaceful trails winding through open meadows and oak and pine forests. Mount Subasio is the expansive mountain on whose slopes Assisi was built. A place of subtle beauty and deep spiritual resonance, it is said that St. Francis once preached here to birds gathered on the branches.

While hiking along the summit meadows, you may encounter grazing sheep, white Chianina cattle, and semi-wild horses before descending about 445 feet to the small, charming hamlet of Collepino for lunch. A welcoming table awaits, laid with a generous antipasto of assorted bruschetta, followed by grilled meats and vegetables.

After lunch, you may choose to return to Spello by van or continue on foot, descending through the forest along a well-maintained trail. The path leads through olive groves and alongside an ancient Roman aqueduct, which once brought drinking water into town from the eastern slopes of the mountain.

This evening’s farewell dinner features another delicious, seasonal meal and the chance to raise a glass—drawn from the restaurant’s exceptional wine cellar—in a toast to your week’s adventures.

Included Meals: Breakfast, Lunch, Dinner

After a leisurely breakfast, you’ll depart Spello and travel to Rome, arriving at the River Palace Hotel at approximately 11:30 a.m. Upon arrival, your tour leaders will offer a brief 45-minute orientation walk to help you get acquainted with the area. Afterward, you’ll bid farewell to your guides and continue on with your onward travels.

Included Meals: Breakfast

City tour of Siena; 2-2.5 hours (approximately 3 miles), easy

Your leaders meet you at 9:00 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 are required.

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 in beauty and 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 leader 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 essential 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.

Included Meals: Lunch, Dinner

7 miles, easy to moderate, 550-ft. elevation gain; optional 3-3.5 miles, easy to moderate (with challenging sections), 750-ft. elevation gain

Today’s exploration begins on the outskirts of San Quirico. After an initial short drive to the village of Torrenieri, step onto a quiet gravel road that meanders along rolling terrain between the Orcia Valley and the Crete Senesi (Sienese hills) toward Pienza, the morning’s destination. This spectacular walk features postcard views of the hill towns and surrounding villas, dotted with cypress and walnut trees. In the spring, expect to see wildflowers in bloom.

Lunch awaits at an old Tuscan farmhouse, where your hosts welcome you with an assortment of local pecorino (sheep’s milk cheese), cold cuts, salads, frittatas, and pickled vegetables accompanied by their house wine and local olive oil. 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. Your route is marked by a long (45-minute) climb along a trail with loose rocks and gravel. It then transitions to gravel road and eventually pavement—culminating at a small hamlet with pretty views over the valley. Upon 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 leaders.

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-renowned 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 of the town’s enoteche (wine bars) or restaurants, for 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). Continue on to our friend’s cantina (or winery), and sample some of the wines for which this region is renowned. Afterward, 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 leaders and fellow travelers for a casual meal served family style, perhaps featuring homemade ravioli and a tagliata (grilled steak) with porcini mushrooms (accompanied by a glass or two of vino) at a local osteria.

Included Meals: Breakfast, Dinner

3 miles, easy; optional 3 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 a (three-hour) 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 leader. Afterward, enjoy lunch at a local restaurant of your choice, with time for independent exploration.

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, and beautiful, 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 leaders will provide recommendations.

Included Meals: Breakfast

5-7 miles, easy to moderate (with challenging sections), 1,220-ft. elevation gain

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 that includes some challenging rocky sections.

After visiting the church and admiring the three ceri contained within, enjoy a scenic funicular ride descending into town, where you savor lunch at one of our favorite osterias. 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 leaders 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).

Included Meals: Breakfast, Lunch

5-7 miles, easy to moderate and optional 2.5 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 (445 feet) 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 forest along a well-maintained trail and 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 feature’s another meal of delicious, seasonal cuisine and an opportunity to toast your week’s adventures with a glass from the restaurant’s outstanding wine cellar.

Included Meals: Breakfast, Lunch, Dinner

After a leisurely breakfast, you depart Spello for Rome. You arrive at Hotel dei Mellini at approximately 11:30 a.m. Your tour leaders provide a brief (45-minute) orientation walk on arrival. Afterward, you bid farewell to your guides and make connections for onward travels.

Included Meals: Breakfast