Start the day with an orientation walk of Città della Pieve with a local guide who will point out landmarks, restaurants, cafes, grocery stores, the bank, pharmacy, post office, and anything else you might need during your stay.

The orientation walk will end at the saffron museum, where you’ll have the opportunity to taste the locally produced saffron that Città della Pieve is famous for. You’ll learn about the intricate cultivation process and why this precious spice has been an important part of the town’s heritage for centuries.

Afterward, we suggest a passeggiata (leisurely stroll) to take in the sights, sounds, and smells of the outdoor cafes and local shops sprinkled around this ancient town.

As you explore, you will see why Città della Pieve won the first Pio Alferano Prize as the most perfect city in Italy. The prize judges said this about the town: “Città della Pieve is a perfect city: it offers the ideal condition of being isolated and close. It is at the center of art with the masterpieces of Perugino, but without the anxiety of frenetic tourism. In the sheltered rooms of beautiful houses, villas, hotels, taverns, and restaurants, day and night, a slight euphoria animates the spirit and shakes the body when in this city.”

Later this evening, we suggest dinner at one of the many restaurants in town.

Included :

• Activities: Citta della Pieve orientation walk; Saffron tasting; Free time
• Meals: Breakfast
• Accommodation: Historic boutique hotel

Head to Tuscany and towards the hilltop town of Montepulciano, famous for its wines. Enjoy some free time in Montepulciano and its panoramic view of the surrounding Tuscan countryside and vineyards. Then, head to one of the oldest wine cellars in town dating back to the 16th century. A wine connoisseur will teach you all about the history of the cellar and the aging process and you’ll get the chance to taste the famous Vino Nobile Montepulciano wines.

Next up is Pienza, a beautiful Renaissance town surrounded by panoramic views of Orcia Valley. This town has been defined as the ideal city thanks to Pope Pius II’s endeavors to transform his hometown into the “perfect town”. You will have some time to wander around Pienza’s hidden alleyways and cobblestone streets and enjoy the small shops in the town center. Don’t miss out on Pienza’s specialty, a pecorino sheep’s milk cheese that you can taste and buy in the town.

Included :

• Activities: Montepulciano free time; Montepulciano wine cellar tour & tasting; Pienza free time
• Meals: Breakfast, Lunch
• Accommodation: Historic boutique hotel

Make your way to Assisi which many of our past travelers have said is their favorite town in all of Italy! Assisi is a hilltop town in the beautiful region of Umbria with charming lanes, massive gates, and stone buildings. The town is famous as the birthplace of St. Francis of Assisi, one of Italy’s most venerated saints, and has attracted pilgrims from all over the world for over 700 years. The Basilica of Saint Francis was built in his honor right after his death and is covered in some of the best-preserved frescoes in all of Italy. After lunch, enjoy some free time to explore. Be on the lookout for unique jewels inspired by Saint Francis that are only made in Assisi.

Included :

• Activities: Assisi tour; Basilica of Saint Francis; Assisi free time
• Meals: Breakfast, Lunch
• Accommodation: Historic boutique hotel

Start your day with a hands-on cooking class at the hotel led by the resident chef. You’ll learn to create fresh pasta from scratch, prepare a variety of delicious sauces that highlight the authentic flavors of the region, and master the art of making the iconic Italian dessert, tiramisu.

Once the cooking is done, sit down to enjoy a leisurely lunch featuring the dishes you’ve just crafted. It’s a perfect moment to savor your creations in the company of fellow travelers, sharing the joy of a true Italian meal.

The afternoon is yours to relax or explore Città della Pieve some more at your own pace. Wander through its medieval streets, discover hidden local gems, or simply unwind in a peaceful café.

Included :

• Activities: Cooking class; Free time
• Meals: Breakfast, Lunch
• Accommodation: Historic boutique hotel

Get ready for an experience far away from the main tourist attractions. Travel along the winding roads of Val d’Orcia where some of Italy’s best pecorino cheese is produced. Surrounded by towering cypress trees and rolling hills stretching toward the blue sky, Val d’Orcia is straight from a postcard!

Spend the day in the heart of the Tuscan countryside with Giancarlo and his brother, the owners of a family sheep and cheese farm. They will share their passion for nature and the secrets of pecorino cheese with you. Learn about how they work the land, raise the animals, and produce cheese as you see, smell, and taste this family’s everyday life over the generations. Not only will you participate in one of the best cheese tastings in Italy, but their infectious enthusiasm will guarantee you leave with a smile on your face!

Included :

• Activities: Sheep farm tour; Cheese making demonstration; Cheese and wine tasting
• Meals: Breakfast, Lunch
• Accommodation: Historic boutique hotel

Spend the morning at an innovative farm in the Umbrian countryside where you’ll see how food is grown, harvested, and brought to the table. You’ll learn about biomimic farming and what it takes to run one of the most biodiverse farms in Europe. After the tour, enjoy a fresh, seasonal brunch with wine right in the vineyard. The rest of the afternoon is yours to relax or explore at your own pace.

Included:

• Activities: Farm visit & brunch 
• Meals: Breakfast, Lunch
• Accommodation: Historic boutique hotel

Both remaining days are completely free to do as you wish. You might spend your time wandering through the medieval streets of Città della Pieve, discovering its historic charm and local treasures. Or perhaps you’ll feel like exploring the surrounding gems of Tuscany and Umbria, with a visit to the Renaissance wonders of Florence, the stunning cathedral in Orvieto, or the captivating medieval city of Siena.

Your host can offer advice on public transportation and assist you with booking private transportation with sufficient notice. Remember that this is a semi-independent trip, therefore you’re free to make your own plans. 

On Day 9, meet up for one last dinner, Italian style!

Included :

• Activities: Free days
• Meals: Breakfast, Farewell dinner (Day 9)
• Accommodation: Historic boutique hotel

Say farewell to Italy and your new friends. Today is the last day of your trip. We hope to see you on one of our next adventures!

Included:

• Activities: Free time; Departure (at your own expense)
• Meals: Breakfast

*Itinerary is subject to change.