Start the day with an orientation walk in the nearby town of Città della Pieve. Your local guide will point out landmarks, restaurants, cafes, and grocery stores as well as the bank, pharmacy, post office, and anything else that you might need during your stay. 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 that evening, we suggest dinner at one of the many restaurants in town.

*A daily shuttle from the villa into town is included in the trip cost.

Included :

• Activities: Citta della Pieve orientation walk; Free time
• Meals: Breakfast
• Accommodation: Villa

Head to Tuscany and towards the hilltop Montepulciano, famous for its wines. On the way, stop at the Sanctuary of the Madonna di San Biagio, a masterpiece of Renaissance architecture. It is also believed to be the exact spot where the Virgin Mary appeared to a shepherd and now, where pilgrims come to pray.

Continue to Montepulciano to enjoy the 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. After lunch, you will have some free time in Montepulciano. There are only a few shops here but if you’re looking for fine Italian leather, you can find some of the most affordable handmade leather goods in the area!

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 at stores in the town.

Included:

• Activities: Sanctuary of the Madonna di San Biagio; Montepulciano wine cellar tour & tasting; Montepulciano free time; Pienza free time
• Meals: Breakfast, Lunch
• Accommodation: Villa

Get ready for an authentic 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, feel, and taste every step of this family's everyday life over the generations. Not only will you experience 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: Villa

All remaining days are completely free to do as you wish. You can choose to relax by the veranda with a glass of wine or explore some more.

Your slowcation leader will have optional activities that you can sign up for such as truffle hunting or the Bagni San Filippo hot springs, one of the best-kept local secrets.

If you don’t want to participate in the optional activities provided, you’re free to make your own plans. There are many neighboring towns that can easily be accessed by train such as Florence, Siena, and Orvieto. Your slowcation leader can offer advice on transportation with sufficient notice.

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

Included :

• Activities: Free days (optional activities at your own expense)
• Meals: Breakfast, Farewell dinner (Day 9)
• Accommodation: Villa