Arrival at Farmhouse

Welcome Dinner
Old world farmThis will be your home for your stay in Cortona. The farmhouse is a 450 year old treasure, and an exquisite example of the art of blending ancient asthetics and modern comfort. Its newest addition, on the right side of the structure, dates to the 1870s. You will be at home in comfort, with a wonderful breakfast and dinner each day.  One of the highlights of LiveTuscan is the time spent at the table, enjoying Tuscan specialities, regional wines and new friends.
The property has a beautiful pool, and wonderful views of the surrounding countryside of Cortona. Cortona itself is an unforgettable destination, dating back to the Etruscans, around 900 b.c. It is a perfectly preserved town, with warm people and a history that predates ancient Rome. Cortona is one of the 12original Etruscan towns, and therefore one of the oldest in Italy. You will be learning much more about this hill town, which was the location of the book and film “Under the Tuscan Sun”tomorrow, on your Cortona tour.

Montipulciano/Pienza and Montalcino

Today you will meet Pino, a charming and expert guide to three of the most important towns for wine and cheese. He is a fascinating man, a geologist who knows the soil and the grapes. He is available to answer the most obscure questions about wine, or anything else that has to do with the Tuscan region. He is an absolute treasure.

Montipulciano is renowned for its walkable nature. The Cantina Contucci is off the Piazza Grande, where you can view how the city’s jail was converted into a wine cellar. The Contucci family claims to have made wine and owned vineyards for over 40 generations, or over 1000 years in the Montepulciano area. Pino will take you to the Contucci cellars, where you will enjoy a wine tasting.

On to Pienza, home of the famous Pecorino cheese. This town has amazing food shops everywhere, and many delicious samples for you to taste. You will have the chance to purchase cheese, and they will vacuum-seal it so that it can be packed in your suitcase for the trip home. The hard part is deciding which variety to buy; there are so many that the choice isn’t easy!


Your final stop for the day is Montalcino, home of the world-famous Brunello wines. You will enjoy some of the most gorgeous scenery on the way from Montipulciano and Pienza to Montalcino. The postcard views are some of the most memorable, and you will be in awe at what nature and man have done together in this region. A wine tasting is offered in Montalcino, and shouldn’t be missed.

Tour of Cortona

Louise, your lovely and knowledgeable guide. She will show you the highlights of this ancient town, your home. She holds a degree in Art History, and a Master’s in Etruscan architecture, and happens to have the answers to almost any question about this magical place. Cortona is located in the province of Arezzo, and is the main cultural and artistic center of the Val di Chiana, after the city of Arezzo.

Following the tour, you will be driven just 3 miles from the town walls to Le Celle, where St. Francis was imprisoned. It is truly an unforgettable stop, with some of the most beautiful scenery in Cortona. Along with Assisi, it is one of the most spiritual places that you will visit. Here the monks have taken a vow of silence, and it lends to the reverence of this very special place. Afterwards, you will have the opportunity to drive by Bramasole, the home of Frances Mayes, author of “Under the Tuscan Sun”.

Cooking Class

A cooking class will be waiting for you when you return home to the farmhouse that afternoon.

Dinner will follow.

Orvieto Driving

Today we will have a guide-free day of exploring beautiful Orvieto, another famous wine hill town. Our driver will show us points of interest along the way, and once we arrive we’ll have the day to shop, eat and discover what makes it one of the most popular places in Tuscany. Rick Steves says that Orvieto is “what an Italian hill town should be”.  On our arrival back at the farmhouse, maybe a swim in the pool before dinner?

Dinner al fresco, whenever possible.


Assisi is a hill town in central Italy’s Umbria region on the western flank of Monte Subasio. It was the birthplace of St. Francis (1181–1226), one of Italy’s patron saints, and St. Clare. The Basilica of St. Francis is a massive, 2-level church, consecrated in 1253. Its 13th-century frescoes portraying the life of St. Francis have been attributed to Giotto and Cimabue, among others. The crypt houses the saint’s stone sarcophagus.

Assisi is now the site of many pilgrimages, and is linked in legend with its native son, St. Francis. The gentle saint founded the Franciscan order and shares honors with St. Catherine of Siena as the patron saints of Italy. He is remembered by many, even non-Christians, as a lover of nature (his preaching to an audience of birds is one of the legends of his life). UNESCO collectively designated the Franciscan structures of Assisi as a World Heritage Site in 2000. You will again meet Marco, your guide of Perugia for an extremely informative tour of this spiritual town.

Montefalco Winery

A fter visiting Assisi, we will have a driving tour to a winery in Montefalco. For many years Montefalco was a closely guarded secret among Italian wine lovers. The main red wine in terms of quantity is the Rosso di Montefalco. This uses the Sangiovese grape that is found in the wines of Chianti but mixes in some of the local Sagrantino grape, which is what makes Rosso di Montefalco special. The Sagrantino grape is said to have more tannin than just about any other grape in the world. You can also find a pure Sagrantino red wine as well as a passito version which is a thick, syrupy wine. Montefalco’s white wine, Grechetto, is also made from a local grape, of the same name as the wine.

After our stop in Montefalco, we will drive home to the farmhouse. Tonight is our special dinner “party” in Cortona. After a stroll through town, we will have a wonderful wine dinner that will be very memorable.



Free Days

One of the most popular activities is to take the train to Florence for a tour or to walk this beautiful city on your own. The train is a very economical and easy way to get to Florence, under 1 ½ hours from Camucia. Rome is 2 ½ hours by train, and another easy destination, even for the day. With the two free days together, traveling farther and staying overnight opens a whole region of possibilities.

All free day transportation and activities are the responsibility of the guests, but I will be happy to help with suggestions for destinations for either one day or an overnight somewhere farther afield.

The Spanish Steps, Roma

The Duomo, Firenze

The Duomo, Firenze

Vespa tours, just relaxing in Cortona, or traveling by train to somewhere new…there are so many possibilities for us on the free days.





Today we have the privilege of seeing one of the most incredible buildings ever created, the Duomo of Siena. Inside and out, it is without a doubt a place that you will never forget. Works of art by every great master of the Renaissance are within its walls. Every inch of space has been filled with art and you will be amazed. We will have a tour with Louise, your lovely guide who taught you many things about Cortona. She will weave a story about the artists and history of this city, and tell how Siena had a major role in shaping the Italian political scene in its early days. The city of Siena is one of the highlights of the week not only because of its historical importance, but for the variety of shops, restaurants and culture that you’ll find all around the city. The historic center of Siena has been declared by UNESCO a World Heritage Site.


Our driver will take us a short distance to Monteriggioni, a charming, walled medieval castle. This beautiful, perfectly intact walled town is in the province of Siena. The town is architecturally and culturally significant. It hosts several piazzas, and is referenced in Dante Alighieri’s Divine Comedy.

We will have free time to explore this little hamlet, then return home, a little over an hour’s drive away.

Dinner under the stars.

Chianti Region and Prada Outlet


Today, our final day, will find us touring the famous Chianti region with our driver. We will stop at points of interest along the way…castles and wineries. There is so much scenic beauty that the drive, along with the driver’s knowledge of the area, is the highlight of the day. This is the region where the famous Chianti Classico (Black Rooster) is created. Some of Italy’s most iconic wines are produced here, and no time in Tuscany is complete without a drive and a taste of Chianti.

O n the way back to dinner at the farmhouse, we will stop at the fun, famous Prada Outlet, outside of Montevarchi. This stop is a cultural one, as well as fun. Did you know that of the world’s leading fashion designers, the vast majority are from Italy? Fashion is one of Italy’s largest exports, and we can consider this a museum of wearable art.


Our farewell dinner will be served under the stars. Memories shared, friendships made, and a farewell to Tuscany.



The city of Perugia is in Umbria, not Tuscany, but is so beautiful it is not to be missed. It has an active cultural life that goes year-round, and the views of Umbria and Tuscany from its particular vantage point must be part of your LiveTuscan experience. Truly one of my favorite cities.

You will meet Marco, one of the best and most memorable guides ever. Perugia is his home, and you will get a thorough and unique perspective on this fascinating city. It’s also the chocolate capital of Italy, home of the Baci factory, and the famous Baci “kisses”.


We will then drive a short distance to Deruta, a town dedicated to the art of Italian pottery. The local clay was potterygood for ceramics, whose production began in the Early Middle Ages, but found its artistic peak in the 15th and early 16th century. The lack of fuel enforced low firing temperatures, but from the beginning of the 16th century, Deruta compensated with its metallic lustre glazes in golds and ruby red. In the 16th century Deruta produced the so-called “Rafaellesque” ware, decorated with fine arabesques on a fine white ground.

Deruta continues to produce some of the finest Italian maiolica. All free time in this town to shop for treasures to ship home.

Back to our home in Cortona, with dinner at the farmhouse, a highlight of each day.

Departure Day

Coffee and pastries will be served for breakfast.

We will be departing the farmhouse by 8:30 am. Those of us taking the train to Florence to either the airport or a hotel can travel together. Those who have arranged for a driver should have them at the farmhouse by 8:30 am.

Ciao Amici!