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 the new Florence tram system to Villa Costanza, where our two vans are waiting. It’s about a 45 minute drive 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 give you a quick introduction 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. During the aperitivo 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.

Our day begins with a walking tour of Castellina, led by our local guide Nicola. He’ll share the history of Castellina, including a visit to the Etruscan tomb just outside the village center.

The rest of the day we’ll spend around the beautiful village of Panzano, sitting on a hilltop on the Chianti wine road, halfway between Florence and Siena. Panzano is known for its 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 Anna. 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 in this beautiful setting.

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 a special 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 almost 4,400 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.

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 Italian gardens, following by 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 on your own in Castellina. There are several different dining options in the village, including an excellent gelato shop just two doors from our hotel.

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 and offering outstanding views of the countryside.

At Nora's Chianti Cashmere goat farmAfter our time 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.

We’ll then 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 will host us for a picnic lunch under the shady fig tree next to her home.

Nora has a very interesting story that always inspires us. You’ll enjoy meeting her and seeing her goats and the beautiful products made from their soft fiber. And hopefully there will be baby goats to cuddle!

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. The grand finale is the sunset, with views extending over the layers of Chianti hills for many miles.

Day Six (Thursday)

We’ll begin this morning in the village of San Donato in Poggio, another walled medieval village. This is Arianna’s home village, and she’ll lead a stroll around the village, introducing us to some interesting aspects of the history, architecture, and life in Tuscany today.

We’ll next travel up into the hills near Impruneta to meet Janet, an American expatriate who has lived here for almost 50 years. We’ll first visit with Janet in a small borgo (hamlet), where she and her family have an olive oil workshop. Janet will tell us much more about olive trees and olive oil… you’ll definitely have a much better appreciation for this staple of Tuscan cuisine. Then Janet and Stefano will welcome us to their home nearby for an truly memorable meal on their terrace. We’ll sample a variety of dishes, many using produce from their large vegetable garden. Stefano cooks bread and meat in his wood-fired oven.

On our way back to Castellina, we’ll visit a terracotta factory in Impruneta, the center for terracotta production in Italy.

Dinner tonight is on your own in Castellina… most people aren’t very hungry after our incredible lunch!

Day Seven (Friday)

San GimignanoIt’s our last day! We’ll journey down our hilltop to the Val d’Elsa, making our way across the valley to the famous town of San Gimignano, perched on a hillside. San Gimignano, a UNESCO World Heritage site, is known for its unique medieval towers, built to enhance the homes of wealthy families. At one time there were more than 70 towers! Today 14 towers remain, along with impressive architecture, a church filled with frescoes, and more incredible views. This is also the best shopping opportunity of our week, so there’s something for everyone here.

We’ll then drive 10 minutes into the countryside to the home and winery of Flavia and Francesco, where they produce Vernaccia di San Gimignano wines, the noted white wines of Tuscany. We’ll learn about the family’s history at this place and visit their winery, then enjoy a special lunch of local products including several dishes featuring saffron grown in this area.

We’ll return to Castellina in the mid-afternoon. You can enjoy an optional visit to the archaeological museum near our hotel (which includes the opportunity to climb to the top of the tower). Other travelers enjoy relaxing by the pool or a final walk around this special village.

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

Day Eight (Saturday)

We’ll have an early breakfast together and then return to Florence, 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!