

7 Days
Starting From
$6,245.00
10 Days
Starting From
$7,295.00
per person, double occupancy
Want more from your experience?
Add an ExtensionExperience a cornucopia of hidden gems on this true insider’s walking tour of Tuscany and Umbria. With their deep knowledge of art history, our Italian leaders show you the Basilica of Assisi’s extraordinary frescoes. In Siena, discover the Palio horse race from the perspective of a local expert—and get exclusive insider access to its famous Duomo. Indulge in local farm-to-table fare at an agriturismo that produces its own cheese and olive oil—exploring the exquisite vintages of Montalcino at a neighboring estate. Keep an eye out for semi-wild horses on the slopes of Mount Subasio and soak your tootsies in the medieval baths at Bagno Vignoni. Along the way, your leaders will take you off the beaten path, immersing you in spectacular scenery, rich cultural traditions, and the warm hospitality of Italian friends.
Country Walkers is proud to support Wine to Water with a donation on behalf of each guest on this tour. Wine to Water is an international organization providing access to clean drinking water and emergency supplies in water-challenged regions. We believe in giving back to the places that have enriched the lives of our guests. We’re committed to identifying and supporting sustainable initiatives in a variety of areas including education, world health, economic equality, safe drinking water, the environment, and the preservation of cultural traditions.
2026 Pre-Tour Extension - Florence
2 Nights From
$
495
per person, double occupancy
Single Supplement: From $395
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.
After enjoying an included breakfast at your hotel, spend the day exploring at your own pace with the help of our provided city information.
Included Meals: Breakfast
After another included breakfast at your hotel, enjoy a full day of independent exploration, using our provided city information to uncover more of the area’s hidden gems and highlights.
Included Meals: Breakfast
25hours Hotel Piazza San Paolino
2025 Pre-Tour Extension - Florence
2 Nights From
$
495
per person, double occupancy
Single Supplement: From $345
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.
After a delicious included breakfast at your hotel, you are free to explore on your own, using our included city information to guide your discoveries.
Included Meals: Breakfast
After a delicious included breakfast at your hotel, you are free to explore on your own, using our included city information to guide your discoveries.
Included Meals: Breakfast
Hotel De La Ville
2026 Post-Tour Extension - Rome
2 Nights From
$
345
per person, double occupancy
Single Supplement: From $295
After enjoying an included breakfast at your hotel, feel free to continue exploring at your own pace, using our provided city information to guide your discoveries.
Included Meals: Breakfast
After another included breakfast at your hotel, enjoy a full day of independent exploration, using our provided city information to uncover more of the area’s hidden gems and highlights.
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
River Palace Hotel
2025 Post-Tour Extension - Rome
2 Nights From
$
395
per person, double occupancy
Single Supplement: From $295
After a delicious included breakfast at your hotel, you are free to explore on your own, using our included city information to guide your discoveries.
Included Meals: Breakfast
After a delicious included breakfast at your hotel, you are free to explore on your own, using our included city information to guide your discoveries.
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
Hotel dei Mellini
We took the Country Walkers guided hiking tour of Tuscany and Umbria immediately after our Dolomites tour with the same company, taking the train from Venice to the starting city of Florence. As with our Dolomites tour, this tour was led by two excellent guides, Alessandro and Manuela – knowledgeable, affable, cheerful and capable. The routes chosen were well thought out, taking us through the classically beautiful scenery – rolling hills decorated with vineyards and olive groves punctuated with sentinel poplars; quaint hillside villages with narrow streets between ancient, well-preserved buildings; informative tours of several towns; and well selected restaurants we would never have found on our own. Great food and wine (well, we were in Tuscany and Umbria!), and very affordable on the few occasions we were on our own for meals (just six Euros for a half liter of vino rosso della casa!). Hotels were all good, and each with its own character. As with our Dolomites tour, everything was taken care of so we could relax and enjoy the whole vacation. The farewell dinner was at Assisi’s most impressive restaurant, La Locanda del Cardinale, with glass floors so you can see the ancient Roman ruins over which the centuries-old restaurant is built – utterly magical. Very classy service and excellent food and wines. A unique and profoundly memorable experience. Our last day travelling to Rome was wonderful too, stopping at Spoleto en route for a tour of this remarkable hillside town before being dropped at our well-located hotel in the center of Rome.
Italy: Tuscany & Umbria
I have high praise for Country Walkers tours,this being my 2nd trip,my first was to Vermont. The gufes are knowledgable about the destination, and attentive to all the details, making it a stress free adventure. The groups tend to bond easily, making it enjoyable for couples,singles, and friends to share the experience.The guides always offered options in the walking experience when possible.It offered a balance of meals together and meals on our own with suggestions from the guides.I look foward to other Country Walker tours..so much more to explore!!
Italy: Tuscany & Umbria
Experience your destination like an insider with people who call it home.
Alessandro Gullo
Alessandro Gullo has Sicilian ancestry and was educated in the US as well as Italy. He is a certified guide of historic monuments who effortlessly combines his charming personality with a vast knowledge of the culture, art, history, food, and wine of Italy.
Costanza D'Amico
Born in Assisi, Costanza D’Amico is fascinated by both ancient and modern cultures. While studying archaeology in Rome, she participated in many excavations among the ruins; while in New York City, Costanza studied modern and contemporary art history. When not guiding tours of her native Umbria, Costanza teaches at a local high school, volunteers as a family counselor, and travels around the world. Costanza loves to prepare delicious Umbrian meals—and also enjoys experimenting with culinary styles from across the globe.
Claudia Piombi-Barnabe
Claudia Piombi-Barnabé infuses all guests with her passion for mountains and professional expertise in geology. A formal mountaineering guide of the Italian Alpine Club (CAI), Claudia brings a high level of precision and safety to all her tours. Her knowledge and love of the mountains is matched only by her appreciation of the Italy’s food.
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