Your Week in Tuscany

A European Experiences week has an ideal balance of structure and flexibility, activities with the group and time on your own. Because our groups are small and we use two vehicles, we sometimes split into two groups or take a few group members on a spontaneous late afternoon excursion. Plans may also be adjusted based on weather, the interests of the group members, and unexpected opportunities. If there’s a special event in the area during your week, we’ll likely rearrange things to be there.

We’ll describe a “typical” week in Chianti, but every Chianti Experience week is somewhat unique. Your week might be organized differently, and for various reasons, experiences may be added or not included. This sample itinerary also doesn’t include some special stops we’d like to surprise you with when we’re together.

Day One (Saturday)

We meet the group at the train station in Florence and travel by chartered bus about an hour to our village of Castellina-in-Chianti. You’ll get to know your fellow travelers and enjoy the scenery as journey to the countryside. Soon we’ll arrive in Castellina and the elegant and welcoming former palace that will be our base for the week.

Castellina in Chianti

You’ll have time to settle into your room, and then we’ll introduce you to Castellina, one of the famous wine towns of Chianti. Our hotel is set at one end of the main street, a terrace and swimming pool adjacent to the vineyards. It’s a perfect location to experience a town and the countryside! This evening we’ll enjoy a welcome aperitivo and dinner together at the hotel’s restaurant. Over dinner we’ll discuss our plans for the week.

Day Two (Sunday)

On our first full day we’ll experience the culture, history, landscape, wine, and cuisine of this beautiful area. We’ll spend the day around the beautiful village of Panzano, sitting on a hilltop, halfway between Florence and Siena.

On the edge of the village we’ll stop at the tiny community of San Leolino and the lovely 12th century parish church, with views across the Conca d’Oro (“golden bowl”), a lush agricultural valley. Panzano’s busy Sunday morning is underway when we arrive. We’ll have time for shopping and a coffee break, as well as a stop at the world-famous butcher shop of Dario Cecchini.

After the market we’ll take a gravel “white road” to Vallone de Cecione, a small family-owned farm and winery in the Conca d’Oro. Our host Francesco and his parents will welcome us for lunch, accompanied by their excellent wine and olive oil. We’ll tour the winery, enjoy the lovely surroundings, and learn about this special family’s history and their life in the Chianti countryside.

Lindsay T - pasta making 4

At the bottom of the Conca d’Oro is a lovely farmhouse, Fagiolari, where we’ll spend the next several hours in a cooking class with Stefania and Giuiletta. This is always a highlight of the week. We’ll split into two groups in the farmhouse kitchen to make several Tuscan specialties: fresh pasta, a main course, a vegetable dish, and dessert. Everyone especially enjoys making the pasta.

It’s a very special environment with two warm and welcoming teachers. As the grand finale of our day, we’ll enjoy the delicious meal the group has prepared.

Day Three (Monday)

We’ll spend most of today in Siena, one of Italy’s loveliest medieval cities and a UNESCO World Heritage Site.

Siena duomoIn the morning we’ll enjoy a walking tour with Antonella, a knowledgeable and fun local guide. She’ll introduce us to the history, architecture, and traditions of Siena, including the system of neighborhood contrade.  We’ll learn about the famous Palio horse race, which takes place twice a year on the Piazza del Campo, one of Europe’s greatest medieval squares. We’ll also visit the beautiful 12th century duomo (cathedral).

Lunch in Siena is on your own, and you’ll have plenty of time to explore. There is some excellent shopping in Siena, including clothes, shoes, gourmet food products, wine, art, artisinal paper, and books.

On our way back to Castellina, we’ll stop at Monteriggioni, a medieval walled village with fourteen towers, dating to the 13th century.

Our good friends Rita and Rosita are our hosts for dinner tonight at their home, a medieval castle on a hill outside of Greve. We’ll enjoy Rita’s traditional homecooking in an idyllic setting.

Day Four (Tuesday)

In the morning we’ll visit the 70 acre Florence American cemetery, the resting place of 4,402 Americans who died in Italy in World War II. It’s a very special place and a reminder that this beautiful corner of Italy wasn’t always so peaceful.

We’ll take a stroll around the lovely medieval village of Montefioralle, sitting on a hilltop.  This is one of our favorite places in Chianti.

Later we’ll visit Vignamaggio, a famous wine estate between Greve and Panzano. The estate once belonged to the family of the woman believed to be Da Vinci’s “Mona Lisa,” and perhaps the famous painting was completed here. We’ll tour the winery and lovely gardens and enjoy lunch and a tasting of Vignamaggio wines.


In the afternoon we’ll visit Greve in Chianti, a major Chianti wine town with a unique piazza. You may want to do some more wine tasting at the Le Cantine, one of the largest and most important wine shops in Italy. (You can taste over 140 wines!) You can also browse in the many small shops, or relax over a drink or gelato. We especially enjoy Grazia Giachi, specializing in handmade linens and embroidery, where you can meet our friend Angela, the 4th generation of women in her family to own this shop. We think you’ll also enjoy the Antica Macelleria Falorni, a large butcher shop that has been in the same spot since 1729.

Dinner tonight is at a restaurant in Castellina.

Day Five (Wednesday)

Our day today will center around the neighboring wine village of Radda in Chianti. Radda is a beautiful medieval town, enclosed by defensive walls.

Lunch in VolpaiaAfter a morning in Radda, we’ll drive up on a neighboring hillside to the tiny village of Volpaia. We’ll explore Volpaia and have a special lunch together on the terrace of a country restaurant, three courses served family style.

After lunch we’ll drive down into the valley to the farm of our friend Nora, an American who has lived in this area for more than 30 years and raises cashmere goats. Nora has a very interesting story; you’ll enjoy meeting her and seeing her goats and the beautiful products made from their soft wool.

Dinner tonight is on your own in Castellina, where you’ll find a variety of restaurants to enjoy. There’s also a grocery store and some smaller food shops where you can buy supplies for a picnic.

Day Six (Thursday)

Today we’ll make a longer day trip to another area of Tuscany, accompanied by our friend Pino. We’ll first visit his town of Cortona, originally settled by the Etruscans. Pino will introduce us to Cortona and its lovely architecture, including an opera house, and you’ll have some time to explore on your own. We’ll have lunch together in Cortona. In recent years the town has been made famous by Frances Mayes (“Under the Tuscan Sun”), and we may even drive by the house featured in the book.

View from CortonaAfter lunch we’ll drive through the countryside to the famous hill town of Montepulciano, with views across the Val d’Orcia. We’ll drive to the top of the town and walk down with Pino as our guide. You’ll especially enjoy our visit to the artisan coppersmith. You’ll have time on your own here too before our return to Castellina.

We’ll have a special dinner tonight at a restaurant high in the Chianti hills in the little village of Lamole. We’ll enjoy a warm welcome from the owner Filippo and his team and a memorable meal in an incredibly beautiful setting.

Day Seven (Friday)

Castellina streetIt’s our last day and we’ll stay close to Castellina, with free time for a walk in the vineyards, shopping, a visit to the Archaeological museum and fortezza, or relaxation by the pool.

In the morning we’ll visit Castamonti, a family-owned farm and winery just outside Castellina. They produce wine, olive oil, and salami made from an ancient Tuscan breed of pigs, the Cinta Senese. We’ll learn more about the Cinta Senese and enjoy a tasting of all their products.

Lunch today is on your own in Castellina. Be sure to save room for gelato; just down the street from our hotel is a tiny shop many consider to be the best gelateria in Tuscany.

In the afternoon we’ll visit the Chianti Sculpture Park, an exhibition of 26 contemporary installations and sculptures by artists from all over the world, beautifully set within the surrounding woodland.

For those interested in Italian ceramics, Kathy will host an optional visit to Rampini Ceramics outside Radda, a producer of handmade pottery since the 15th century. You can look, buy, or even order custom pieces.

Our farewell dinner tonight is in Castellina. We’ll make a toast to new friends and our Chianti experiences.

Day Eight (Saturday)

We’ll have an early breakfast together and then return to Florence by our chartered bus, one last journey together. Some will enjoy Florence for a few days and others will continue their travels by train or air. We know you’ll take with you the memories of a wonderful week!