Discover a region of valleys and vineyards on an Umbria and Tuscany walking tour that blends glorious Renaissance cities with spectacular landscapes.

The stunning Umbria and Tuscany regions boast a quintessentially Italian culture, abundant with history, art, and architecture. Called the cradle of the Renaissance, this is the birthplace of incredible artists, the home of glorious cathedrals, and the setting for stonework masterpieces. Explore the Italian countryside, making your way through spectacular valleys and vineyards past grape arbors, swaying wheat fields, and rustic farmhouses. Warm and welcoming, the people here are passionate about their wine, which pairs perfectly with the unpretentious—and incredibly delicious – local cuisine. Comfortable accommodations include elegant hotels, historic inns, and tranquil countryside retreats. A region of refinement and pastoral splendor, on this Umbria and Tuscany walking tour you’ll discover a landscape and culture that will entice you to return again and again.

Highlights

  • With an expert guide, discover Giotto’s 28-part fresco, The Life of St. Francis, which graces the walls of Assisi’s iconic Basilica of St. Francis
  • Savor an unforgettable meal of Umbrian cuisine as you peer through the glass bottom of a remarkable restaurant that sits atop excavated Roman ruins
  • Trek a dramatic path through an isolated valley of wheat fields and olive groves to the 12th-century, Romanesque Abbey of Sant’Antimo
  • Experience the architectural beauty of Siena’s famous Piazza del Campo (home to the world-renowned Palio horse race), as your local guide regales you with stories
On all Fully-Guided Adventures you can count on...
Icon of road-signs
Expert local guides to introduce you to the best of your destination.
Icon of map
Off-the-beaten-path places you’d never find on your own.
Icon of cutlery
Delicious, authentic multi-course meals — virtually all are included.
Icon of hikers
A maximum of 18 fun-loving fellow travelers to share the journey.
Icon of house
Gracious accommodations that are a clean, comfortable home away from home.
Icon of check-list
Experts to handle all the details.
Icon of airplane
Flight + Tour Combos include plane tickets, airport shuttles, and pre- and post-tour accommodations.

Itinerary

Fri, May 8 to Sun, May 17 - 2020

Show Itinerary:

Begin your adventure by departing from a convenient gateway city in the United States or Canada. Spend the first night aloft.

Upon your arrival at Florence’s Peretola (formerly known as Amerigo Vespucci) Airport, a representative holding a Country Walkers sign meets you as you exit the baggage-claim area. A complimentary small-group transfer will be provided to Hotel de la Ville in Florence, approximately 30 minutes away. The remainder of the day is at your leisure (no meals included).

If you are going to be delayed meeting our transfer representative for more than 15 minutes due to delayed or lost luggage, please contact One Call travel assistance to advise of your delay and they will contact our transfer service on your behalf. Our drivers are generally able to wait for up to 45 minutes from the time your flight lands, after which you would be responsible for your own transfer.

Please note: If you arrive early, and your hotel room is not available prior to the designated check-in time, you may store your luggage with the reception desk.

Accommodation: Hotel de la Ville, Florence

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 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.)

Accommodation: Hotel Dei Mellini, Rome

Ciao!This morning, a complimentary small-group transfer is provided to Rome’s Leonardo da Vinci Airport based on your departure time. (Your transfer time will be communicated to you by your guides on tour.)

Sun, May 10 to Sat, May 16 - 2020

Show Itinerary:

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 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.

Linger Longer with a Tour Extension

Italy: Portofino & Cinque Terre 1
Pre-Tour

Pre-Tour Extension - Florence

  • Two nights at the Hotel de la Ville
  • Small-group airport and hotel transfers
  • Two breakfasts

2 Nights From $398
per person, double occupancy

Please refer to your air itinerary for your specific flight details.

Upon your arrival at Florence’s Peretola (formerly known as Amerigo Vespucci) Airport, a representative holding a Country Walkers sign meets you as you exit the baggage-claim area. A complimentary small-group transfer will be provided to your hotel in Florence, approximately 30 minutes away. The remainder of the day is at your leisure (no meals included).

If you are going to be delayed meeting our transfer representative for more than 15 minutes due to delayed or lost luggage, please contact One Call travel assistance to advise of your delay and they will contact our transfer service on your behalf. Our drivers are generally able to wait for up to 45 minutes from the time your flight lands, after which you would be responsible for your own transfer.

Please note: If you arrive early, and your hotel room is not available prior to the designated check-in time, you may store your luggage with the reception desk.

Accommodation: Hotel de la Ville

Today, delight in the world-renowned art, history, culture, and cuisine of this legendary city on the Arno River. From the layer-cake jewelry shops of the medieval Ponte Vecchio to the Medici art treasures of The Uffizi, you have time to experience it all while staying in the city’s historic center.

Lunch and dinner are on your own while in Florence; there are many fine restaurants or trattorias to choose from during your stay.

Accommodation: Hotel de la Ville

From your centrally located hotel, you have ample time today to stroll through the Galleria dell’Accademia to witness Michelangelo’s David and numerous other Renaissance masterpieces. This afternoon, spend time admiring the spectacular architecture of the Duomo. Perhaps even climb the 463 steps to the top of the cupola.

In the evening, you might relax and sample local vintages in a quiet wine bar.

Accommodation: Hotel de la Ville

The Coliseum
Post-Tour

Post-Tour Extension - Rome

  • Two nights at the Hotel Dei Mellini
  • Small-group airport and hotel transfers
  • Two breakfasts

2 Nights From $348
per person, double occupancy

After breakfast, you have ample opportunity to experience the stunningly preserved monuments and hidden treasures that make this city famous, from the renowned Spanish Steps, where the poet Keats lived and died, to the opulent Trevi Fountain, where Anita Ekberg danced in La Dolce Vita. Tonight, choose from some of the foremost restaurants on Earth to dine in. (Lunch and dinner are on your own.)

Accommodation: Hotel Dei Mellini

From your centrally located, four-star boutique hotel, you have another day to explore the many treasures of this famous city. Delight in the arts of the Vatican, which go far beyond well-known pieces such as the Pieta and Michelangelo’s Sistine Chapel, or spend an idyllic afternoon in the gardens of the Villa Borghese, one of Europe’s most elegant parks. Be sure to sip cappuccino, savor Italian wine, and take time to enjoy la dolce vita.

Accommodation: Hotel Dei Mellini

Ciao!This morning, a complimentary small-group transfer is provided to Rome’s Leonardo da Vinci Airport based on your departure time. (Your transfer time will be communicated to you by your guides on tour.)

What's Included

Flight + Tour Combo
Tour Only
Exceptional boutique accommodations Check Check
All on-tour meals except 2 dinners Check Check
Local guides with you throughout tour Check Check
Local wine and/or beer with dinner Check Check
Entrance fees and special events as noted in the itinerary Check Check
Travel assistance available 24/7 provided by One Call International Check Check
Roundtrip airfare Check
One extra night in Florence and one extra night in Rome Check
Airport car service for arrival & departure Check
Pre- and post-tour breakfasts Check
Business-class upgrades available Check
Morocco: Marrakesh, Foothills of the High Atlas & Essaouira

Dates & Prices

Flight + Tour Combo

10 days. Includes round-trip international airfare, airport car service, additional hotel nights with included breakfast, and your tour.

Single Supplement: From $748

Departing From New York, NY (JFK)

Other departure cities available. Call our Tour Consultants for pricing.

Tour Only

7 days. Includes your tour only.

Single Supplement: From $448

Fri, Sep 20 - Sun, Sep 29

$6,148

Reserve Online

Sun, Sep 22 - Sat, Sep 28

$5,098

Reserve Online

Fri, Oct 11 - Sun, Oct 20

$6,148

Reserve Online

Sun, Oct 13 - Sat, Oct 19

$5,098

Reserve Online

Flight + Tour Combo

10 days. Includes round-trip international airfare, airport car service, additional hotel nights with included breakfast, and your tour.

Single Supplement: From $648

Departing From New York, NY (JFK)

Other departure cities available. Call our Tour Consultants for pricing.

Tour Only

7 days. Includes your tour only.

Single Supplement: From $398

Fri, May 8 - Sun, May 17

$5,998

Reserve Online

Sun, May 10 - Sat, May 16

$5,148

Reserve Online

Fri, May 29 - Sun, Jun 7

$6,048

Reserve Online

Sun, May 31 - Sat, Jun 6

$5,148

Reserve Online

Fri, Sep 18 - Sun, Sep 27

$6,048

Reserve Online

Sun, Sep 20 - Sat, Sep 26

$5,148

Reserve Online

Fri, Oct 9 - Sun, Oct 18

$5,998

Reserve Online

Sun, Oct 11 - Sat, Oct 17

$5,148

Reserve Online

Jump To:

Expert Local Guides

Experience your destination like an insider with people who call it home.