Experience small town Italy like a local on our semi-independent trip… Tuscany conjures up dreams of life at a slower pace where you can soak in the culture, food, and picturesque vistas of the Italian countryside. Stroll through narrow passageways of medieval villages perched on hilltops. Pick out cheese & wine at the market in town and chat with the locals. Then, head back to your 18th-century villa passing olive groves in time for an amazing sunset. Tuscany is the dream vacation and now is your chance!

Live like a local: Sip on espresso & people-watch at a sidewalk cafe in town. Stop by the local grocery store for provisions to prepare a family-style meal in the villa’s fully-equipped kitchen. End the day with a glass of fine wine in your new home.

Ideal location: Most villas in the region are 7 kilometers on average to the closest town & you’d need a rental car during your trip. Our villa is only a 15 to 20-minute walk into town with charming shops, cafes, and restaurants.

Discover Italy: Many of Tuscany & Umbria’s most famous towns are only 30 – 45 minutes away from the villa so you can explore all the best locations in the region without going far. 

Welcome to Italy! Transport to your private villa in the hills of Umbria is included.* Upon arrival, your trip host will greet you and you can enjoy some welcome drinks and hors d’oeuvres. You have the rest of the day to explore your new home.

Later that evening, there will be a welcome dinner at the villa as you get to know your fellow travelers.

*Airport pick-up is only included if you are arriving on Day 1 or if you are staying in Rome before the trip begins. If you are arriving at another date or city, airport pick-up is not included.

Included :

• Transfers: Rome - villa by private car/van (approx. 2 hours)
• Activities: Villa transfer; Welcome drink & hors d’oeuvres, Welcome dinner
• Meals: Dinner
• Accommodation: Villa

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

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: Villa

Experience a unique and immersive journey through the art of agriculture at an innovative farming project in the beautiful Umbrian countryside. Follow your food from the soil to your fork and learn about the hard work and dedication behind every step of the cultivation process. Not only will you better understand where your food comes from, but you'll also gain valuable insights into sustainable farming at one of the most biodiverse farms in Europe! After the farm visit, enjoy a fresh brunch at the heart of the farm's vineyard with wine and fabulous views! The rest of the afternoon is free.

Included:

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

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 trip host will have optional activities that you can sign up for. 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 trip host can offer advice on transportation with sufficient notice.

On Day 10, 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 10)
• Accommodation: Villa

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.