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Guided Walking : Europe

Italy: Tuscany & Umbria

Easy to Moderate Terrain: 4 - 8 miles daily

Italy: Tuscany & Umbria Guided Walking Map

As you cross the lavish inlaid mosaic floor of the Duomo di Siena, vaulted by striped marble columns and surrounded by the brilliance of inlaid gold, you’ll see why Tuscany and Umbria are called the cradle of the Renaissance. From the glorious cathedrals and stonework piazzas of medieval cities to the stately rows of sun-dappled olive trees, the region boasts a refinement and pastoral splendor that is quintessentially Italian. In this spectacular setting, you’ll walk a landscape of grape arbors, swaying wheat fields, and rustic farmhouses, stopping to explore Etruscan ruins along the way. You’ll savor a bounty of sophisticated cuisine in renowned restaurants and family-run trattorias: fine cured meats, exquisite wine, shaved black truffles, traditionally pressed olive oil, and handmade pasta. Climbing to the summit of Mount Subasio— where St. Francis once preached to the birds—you’ll pass through open meadows and wild oak forest, drinking in views of the surrounding valley beyond. Like the tang of aged pecorino cheese, the region’s delectable essence will linger with you long after you’ve departed.


Tour Highlights:
  • Marvel at Giotto’s 28-part fresco The Life of St. Francis, which graces the walls of the iconic Basilica of St. Francis, passionately interpreted by your expert guide.
  • Partake in an unforgettable dining experience in Assisi, where your table sits atop a glassed-in excavation of Roman ruins.
  • Discover the mystical 12th-century Romanesque Abbey of Sant’Antimo surrounded by wheat fields and olive groves.
Flight + Tour Combo

10 days, 9 nights

FROM $6,148 USD

per person, double occupancy

Tour extensions available
Florence
2 nights $398*
Rome
2 nights $448*

Tour Only

7 days, 6 nights

FROM $5,098 USD

per person, double occupancy



Request Reservation Online Contact Us

OR Call to Book 800.234.6900

Your Tour Includes:

  • All meals except two dinners
  • Local wine and/or beer with dinner
  • Exceptional boutique accommodations
  • Local Guide(s) with you 24/7

Flight + Tour Combo Includes:

  • All tour inclusions
  • International round-trip airfare
  • Pre- and post-tour night accommodations
  • Overseas airport transfers
  • Breakfasts
  • Business-class upgrades available

Itinerary & Accommodations

View the Tour Only Itinerary Open
Download Full Itinerary
Day 1

Join your Country Walkers Italy: Tuscany & Umbria tour

2 hours, easy

Your guides meet you in the lobby of Hotel de la Ville, Piazza Antinori, 1, in Florence at 9:30 a.m. Your guides will be wearing a Country Walkers shirt. Please be dressed for walking.

Departing from Florence, embark on a walking tour of beautiful Siena, whose seashell-shaped campo is one of Tuscany’s most distinctive main squares. Afterward, transfer to your country-house hotel in the charming town of Montalcino.

Accommodation: Si Montalcino Hotel & Restaurant, Montalcino

Breathtaking views of the Val d’Orcia await you at the renovated Si Montalcino Hotel and Restaurant. Located just 2½ miles from Montalcino Castle and only about a half mile from the city’s medieval walls, the hotel features cozy rooms and free Wi-Fi throughout. Si Montalcino prides itself on its cuisine, from its hearty breakfast buffets to gourmet dishes featuring fresh local ingredients. Enjoy the onsite pool, and perhaps raise a glass of Brunello while watching the sun set from Belvedere Terrace.

Day 2

Torrenieri to Pienza and Bagno Vignoni

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

Walk through rolling terrain near Torrenieri, stopping for lunch at a Tuscan farmhouse. Afterward, shuttle to the harmonious center of Pienza, redesigned to be the “ideal Renaissance town” by native son Pope Pius II in the 15th century.

Accommodation: Si Montalcino Hotel & Restaurant, Montalcino

Breathtaking views of the Val d’Orcia await you at the renovated Si Montalcino Hotel and Restaurant. Located just 2½ miles from Montalcino Castle and only about a half mile from the city’s medieval walls, the hotel features cozy rooms and free Wi-Fi throughout. Si Montalcino prides itself on its cuisine, from its hearty breakfast buffets to gourmet dishes featuring fresh local ingredients. Enjoy the onsite pool, and perhaps raise a glass of Brunello while watching the sun set from Belvedere Terrace.

Day 3

Montalcino to Sant'Antimo Abbey

4-7 miles, easy to moderate

Walk to the isolated Romanesque Abbey of Sant’Antimo, traversing gentle hills planted with olive groves and Sangiovese Grosso grapes. This afternoon, drive through rolling hills to your elegant hotel in the ancient walled town of Spello.

Accommodation: Hotel La Bastiglia, Spello

Located in a former 16th-century grain mill in the walled medieval town of Spello, this elegant hotel boasts a wide terrace with panoramic views overlooking the Chiona Valley, an on-site restaurant, prestigious wine cellar, and outdoor swimming pool.

Day 4

Gubbio

5-7 miles, easy to moderate

Today, you discover Gubbio, another Umbrian medieval gem. From the mountaintop Church of Saint Ubaldo, your morning walk leads to Gubbio’s spacious central piazza, flanked by stunning palazzi (palaces). Indulge in a gelato before returning to Spello.

Accommodation: Hotel La Bastiglia, Spello

Located in a former 16th-century grain mill in the walled medieval town of Spello, this elegant hotel boasts a wide terrace with panoramic views overlooking the Chiona Valley, an on-site restaurant, prestigious wine cellar, and outdoor swimming pool.

Day 5

Assisi city tour and Spello countryside

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

Explore the quintessential Umbrian hill town of Assisi, beloved for its medieval charm and strong associations with St. Francis, on a guided tour. This afternoon, enjoy free time in Assisi or Spello, or a walk through the lush surrounding countryside.

Accommodation: Hotel La Bastiglia, Spello

Located in a former 16th-century grain mill in the walled medieval town of Spello, this elegant hotel boasts a wide terrace with panoramic views overlooking the Chiona Valley, an on-site restaurant, prestigious wine cellar, and outdoor swimming pool.

Day 6

Assisi to Spello via the Natural Park of Mount Subasio

5-9 miles, easy to moderate

Walk through the serene Natural Park of Mount Subasio, where St. Francis famously preached to the birds. After your lunch in the charming hamlet of Collepino, an optional afternoon hike returns to Spello through olive groves and alongside an ancient Roman aqueduct. Tonight’s farewell dinner features fine Umbrian cuisine.

Accommodation: Hotel La Bastiglia, Spello

Located in a former 16th-century grain mill in the walled medieval town of Spello, this elegant hotel boasts a wide terrace with panoramic views overlooking the Chiona Valley, an on-site restaurant, prestigious wine cellar, and outdoor swimming pool.

Day 7

Your Italy: Tuscany & Umbria tour concludes

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

View the Flight + Tour Combo Itinerary Close
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Flight

Overnight Flight from USA to Florence, Italy

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

Arrival

Arrive in Florence, Italy

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. Please note that there may be up to a 45-minute wait if there are other guests arriving within the same time frame. 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).

Accommodation: Hotel de la Ville (or equivalent), Florence

Hotel de la Ville is an elegant, 4-star property ideally situated on the famous Via Tornabuoni and a short stroll to the Arno River, the Ponte Vecchio, and Florence’s main attractions. All rooms feature luxury and classic décor, and the hotel is renowned for its traditional hospitality.

Day 1

Join your Country Walkers Italy: Tuscany & Umbria tour

Breakfast is included at your hotel.

Your guides meet you in the lobby of Hotel de la Ville, Piazza Antinori, 1, in Florence at 9:30 a.m. Your guides will be wearing a Country Walkers shirt. Please be dressed for walking.

Departing from Florence, embark on a walking tour of beautiful Siena, whose seashell-shaped campo is one of Tuscany’s most distinctive main squares. Afterward, transfer to your country-house hotel in the charming town of Montalcino.

Accommodation: Si Montalcino Hotel & Restaurant, Montalcino

Breathtaking views of the Val d’Orcia await you at the renovated Si Montalcino Hotel and Restaurant. Located just 2½ miles from Montalcino Castle and only about a half mile from the city’s medieval walls, the hotel features cozy rooms and free Wi-Fi throughout. Si Montalcino prides itself on its cuisine, from its hearty breakfast buffets to gourmet dishes featuring fresh local ingredients. Enjoy the onsite pool, and perhaps raise a glass of Brunello while watching the sun set from Belvedere Terrace.

Day 2

Torrenieri to Pienza and Bagno Vignoni

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

Walk through rolling terrain near Torrenieri, stopping for lunch at a Tuscan farmhouse. Afterward, shuttle to the harmonious center of Pienza, redesigned to be the “ideal Renaissance town” by native son Pope Pius II in the 15th century.

Accommodation: Si Montalcino Hotel & Restaurant, Montalcino

Breathtaking views of the Val d’Orcia await you at the renovated Si Montalcino Hotel and Restaurant. Located just 2½ miles from Montalcino Castle and only about a half mile from the city’s medieval walls, the hotel features cozy rooms and free Wi-Fi throughout. Si Montalcino prides itself on its cuisine, from its hearty breakfast buffets to gourmet dishes featuring fresh local ingredients. Enjoy the onsite pool, and perhaps raise a glass of Brunello while watching the sun set from Belvedere Terrace.

Day 3

Montalcino to Sant'Antimo Abbey

4-7 miles, easy to moderate

Walk to the isolated Romanesque Abbey of Sant’Antimo, traversing gentle hills planted with olive groves and Sangiovese Grosso grapes. This afternoon, drive through rolling hills to your elegant hotel in the ancient walled town of Spello.

Accommodation: Hotel La Bastiglia, Spello

Located in a former 16th-century grain mill in the walled medieval town of Spello, this elegant hotel boasts a wide terrace with panoramic views overlooking the Chiona Valley, an on-site restaurant, prestigious wine cellar, and outdoor swimming pool.

Day 4

Gubbio

5-7 miles, easy to moderate

Today, you discover Gubbio, another Umbrian medieval gem. From the mountaintop Church of Saint Ubaldo, your morning walk leads to Gubbio’s spacious central piazza, flanked by stunning palazzi (palaces). Indulge in a gelato before returning to Spello.

Accommodation: Hotel La Bastiglia, Spello

Located in a former 16th-century grain mill in the walled medieval town of Spello, this elegant hotel boasts a wide terrace with panoramic views overlooking the Chiona Valley, an on-site restaurant, prestigious wine cellar, and outdoor swimming pool.

Day 5

Assisi city tour and Spello countryside

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

Explore the quintessential Umbrian hill town of Assisi, beloved for its medieval charm and strong associations with St. Francis, on a guided tour. This afternoon, enjoy free time in Assisi or Spello, or a walk through the lush surrounding countryside.

Accommodation: Hotel La Bastiglia, Spello

Located in a former 16th-century grain mill in the walled medieval town of Spello, this elegant hotel boasts a wide terrace with panoramic views overlooking the Chiona Valley, an on-site restaurant, prestigious wine cellar, and outdoor swimming pool.

Day 6

Assisi to Spello via the Natural Park of Mount Subasio

5-9 miles, easy to moderate

Walk through the serene Natural Park of Mount Subasio, where St. Francis famously preached to the birds. After your lunch in the charming hamlet of Collepino, an optional afternoon hike returns to Spello through olive groves and alongside an ancient Roman aqueduct. Tonight’s farewell dinner features fine Umbrian cuisine.

Accommodation: Hotel La Bastiglia, Spello

Located in a former 16th-century grain mill in the walled medieval town of Spello, this elegant hotel boasts a wide terrace with panoramic views overlooking the Chiona Valley, an on-site restaurant, prestigious wine cellar, and outdoor swimming pool.

Day 7

Your Italy: Tuscany & Umbria tour concludes

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

Accommodation: Hotel Dei Mellini, Rome

Located on the west bank of the Tiber River near the Spanish Steps, the Piazza Navona, and the Vatican, this elegant city-center hotel offers access to Rome’s monuments, shopping, and dining. Guestrooms and public spaces are in the classic umbertino style of 19th century Italy, with tastefully updated rooms, a beautifully landscaped rooftop patio, and modern gym. Amenities include free wireless internet, in-room massage, and complimentary use of bicycles.

Departure

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

Add a Tour Extension to Your Flight + Tour Combo
Pre-Tour Extension: Florence

2 nights from only $398*

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

For those guests reserving our Flight + Tour Combo, you may wish to further extend your time in Italy and explore independently with an additional two nights in Florence. 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’ll have time to experience it all while staying in an elegant four-star property in the heart of the historic center. Stroll through the Galleria dell’Accademia to witness Michelangelo’s David and numerous other renaissance masterpieces. Sample local vintages in a quiet wine bar. Spend an afternoon admiring the spectacular architecture of The Duomo, an ornate masterpiece of pink, white, and green marble.

Single Supplement: $298

*Please note that some hotel city taxes may need to be paid locally.

Post-Tour Extension: Rome

2 nights from only $448*

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

To walk in Rome is to feel the ebb and swirl of 3,000 years of living history—an enchanting melánge of Roman ambition, Baroque decadence, and modern-day moda-italiana chic. During your stay in the Eternal City, you’ll have ample opportunity to explore independently and 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. Delight in the art treasures of the Vatican and feast at some of the foremost restaurants on earth. Through it all, enjoy the comfort and convenience of a centrally located four-star boutique hotel.

Single Supplement: $348

*Please note that some hotel city taxes may need to be paid locally.

Tour Extensions Available

Florence
2 nights from only $398*

Rome
2 nights from only $448*

Learn More

Ready to take the next step?

Request A Reservation

OR Call 800.234.6900

Dates & Prices

Tour Only

2019 Dates Per person, double occupancy Single Supplement
more info
May 12 - May 18 $5,098 $448
Jun 2 - Jun 8 $5,098 $448
Sep 22 - Sep 28 $5,098 $448
Oct 13 - Oct 19 $5,098 $448

Flight + Tour Combo

2019 Dates NEW YORK Change Departure Airport
Flight + Tour Combo
more info
 Flight + Tour Combo
more info
 Single Supplement
more info
May 10 - May 19 $6,148
$748
May 31 - Jun 9 $6,248 $748
Sep 20 - Sep 29 $6,148 $748
Oct 11 - Oct 20 $6,148 $748
Additional gateway cities available; please call for details. Standard Terms & Conditions apply when purchasing this trip. Prices include all airline surcharges and Government taxes and fees. Call for details. All prices are subject to change. Departure dates and prices shown may be updated several times daily, and apply to new bookings only. We reserve the right to correct errors.

Guides

Guides

Our guides' experience, dedication, and enthusiasm make them ideal ambassadors for your destination. They chart the course, finesse the details, and speak the language (English, as well as the local language). They also possess a truly rare skill, knowing when to let serendipity and inspiration take the lead.

Manuela Ciri
Manuela Ciri

Manuela Ciri was born and raised on a farm in Umbria where she has been involved in leading cooking lessons and olive oil tastings. Educated both in Italy and in the US, she is a botanist, herbal healer, and certified environmental guide; her vast knowledge of nature, agriculture, and traditional food is warmed by her sunny smile and joyful nature. When not guiding, she teaches environmental education in public schools, works on landscape engineering projects, or can be found scouting new trails around the mountains and hills of central Italy.

Alessandra Gullo
Alessandro Gullo

Alessandro Gullo is a native of Italy with Sicilian ancestry. Educated in the US as well as Italy, he is a certified guide of historic monuments in Umbria. He combines his charming personality with a vast knowledge of culture, art, history, food and wine on many of our Italian tours.

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