Itinerary - Wine & Cooking in the Heart of Chianti and Florence, Tuscany

Places Florence-Peretola Airport (FLR); Radda in Chianti
Classes & Experiences n/a

Dinner: Welcome Dinner at La Loggia del Chianti (Included)

For our week in Chianti, we offer a free shuttle pick up from the Florence airport today at 2:30 PM. If you are already in Italy, you can make your way by train to the Florence Rifredi train station, and get a taxi that will bring you to the airport in a few minutes. For those arriving at times that do not coincide with our shuttle schedule, we can arrange for a private driver to bring you to Radda in Chianti for an extra charge.

Once in Radda we will help you get checked into your room for the week and give you some time to get settled in, unpack and rest up. As you get settled in, you will find some snacks and drinks waiting for you when you get to your room.

At around 6PM, we will meet on the terrace of the Palazzo for a little Proseco and local salames and cheeses as we get to know one another and discuss the week ahead.

Our welcome dinner tonight will be at "Loggia del Chianti" A short walk from the hotel, this restaurant not only has delicious local fare, but also spectacular views of the beautiful rolling hills of the Chianti wine country.

For dinner tonight, we’ll start out with some local salamis & bruschetta for appetizers, followed by a 1st course of Panzerotti & Pici Pasta. Our second course will be Tagliata – Sliced Tuscan Steak w/ Balsamic Vinegar. For dessert, we’ll have a very traditional local favorite, Cantucci which is the Tuscan-style of Almond Biscotti. Of course we’ll need to dip them in the sweet and sultry Vin Santo wine.

As always, wine is provided with all dinners, and we favor small local wineries wherever we dine. Tonight's wine will be Tuscan Chianti from nearby vineyards.

Places Radda in Chianti
Classes & Experiences

Wine Tasting Class with Sommelier (included)
Cooking Class (included) resulting in dinner
App: Pomodori Toscana al Forno
1st: Spinach and Ricotta Gnudi
2nd: Pork Fillet in Chianti Wine Sauce
Dessert: Limoncello-Rasberry Tiramisu’


Breakfast: Buffet at At Palazzo Leopoldo (included)
Lunch: : At Palazzo San Niccolo (included)
Dinner: The meal we prepare in cooking class (included)

Our first full day in Tuscany, we’ll enjoy the morning relaxing at our beautiful hotel and the town of Radda. You’ll have some time on your own to take in the charming surroundings of this Tuscan town with spectacular vistas of the Tuscan hills. Spa services and massages are also available. A great way to start out the vacation week before we hit the ground running!

We begin our oenological journey at Palazzo San Niccolo in Radda with a certified sommelier to kick-off our week featuring Tuscan wines. We’ll relax in the outdoor courtyard and gardens of the palazzo as we learn and discover what all those crazy wine terms like sulphites, tannins, acidity, balance and body actually mean. We will be treated to a tasting and pairing while learning about the intricacies of these world-renown wines such as Chianti Classico, Brunello and Vino Nobile. After learning about so many complex flavors and senses that encompass wine, we’ll all be able to impress our friends with our wine-snobbery in no time! Afterwards, our group will dine on an exclusively prepared lunch here at the palazzo.

After lunch, we will have a little time to rest at the palazzo before we start our first cooking class of the week. This afternoon's class will be a full four course meal that will result in tonight's dinner, and it is all based on local Tuscan specialties.

Our instructor has been instructing cooking classes here in Central Tuscany for ages.

For our appetizer, we will be making baked tomatoes with local herbs and spices. Our first course will be a Spinach and Ricotta Gnudi - a dish similar to Gnocchi, but made with ricotta! For our second course, we will be preparing a pork fillet in a Chianti wine sauce. Finally, for dessert, we will make Limoncello-Rasberry Tiramisu’.

As always, class is 100% hands-on, so today we will get right into it! Once class is over, we will sit down and enjoy the meal we prepared together for dinner before calling it a night.

Places Montalcino; Montepulciano; Pienza; Radda in Chianti
Classes & Experiences

Private Winery Tours & Tastings with the owners of the wineries. (included)


Breakfast: Buffet at At Palazzo Leopoldo (included)
Lunch: : At Piombaia Winery (included)
Dinner: At De Ricci Winery (included)

After our morning breakfast we will head out for a day full of wine, cheese & more in beautiful Southern Tuscany.

Today you will be treated not only to amazing views, but two very special wineries that are very closely tied to us. As you experience the connections today, you are sure to discover that you are part of something truly unique and special in Tuscany. That is, our relationship is not like other tour companies. These are our close and dear friends.

We'll start off heading towards the town of Montalcino. To get there, we will be driving the famous Orcia Valley Wine Trail (An UNESCO World Heritage Site). This picturesque wine region evokes the classic image of Tuscan rolling hills and cypress trees. This is the area of Tuscany that most of us think of and have seen in many well-known movies such as Under the Tuscan Sun, Life is Beautiful, and many more.

Montalcino is home of what is arguably the best of all Italian wines: Brunello. Instead of going to the big wineries for impersonal tastings like the tourists, we will visit the small, private Piombaia winery in Montalcino. This is the only winery we have ever encountered that makes a truly artisan wine. That is, all of their grapes are hand-picked & selected, and all of pressing is done with a manual wine press, the way it has been done for millennia. Roberto and his family only produce about six-thousand bottles of Brunello per year here, making it something truly exclusive. However, their pricing doesn't reflect the exclusivity of this wine, except that you can only get it here.

On those "just right" days we will be on the terrace under the vines, otherwise in their cozy dining room we’ll be treated to a flight of their different vintages as well as their wonderful Brunello wine. After the tasting, we will be hosted to a Tuscan lunch with the owners of the estate. As we have lunch together, they will share their family history with you and answer any question you can imagine. You are sure to fall in love with this gracious family. It is always one of the major highlights on our weeks, and provides for a truly exclusive and unique Brunello experience. Time and weather permitting, after lunch, we’ll have a private tour of their vineyards before we move on.

Next, we'll drive to the beautiful Tuscan town of Pienza (Also an UNESCO World Heritage Site) – Famously known for its incredible Pecorino cheese. You will have some time to walk around this charming village, do some Pecorino cheese tastings and some shopping before we leave for the town of Montepulciano, where we will do our final wine tasting, tour (and dinner) of the day.

Montepulciano is known for its Vino Nobile wine, a primary competitor for Brunello. Here we will have a personal tour by the owner, Enrico, of his ancient 14th century cellar that was built underneath the Palace of Cardinal Ricci. This truly unique cellar is widely considered to be the most beautiful wine cellar in the world. Those that have seen the 2009 film 'New Moon' (The sequel to 'Twilight') will recognize this wine cellar and other areas of town from the movie.

During our visit with Enrico you will get a better feeling for how connected Culture Discovery Vacations is to this place, as well as the Brunello winery we visited today. You are sure to hear stories about the wines we are producing together, and how an unlikely friendship of otherwise competitors was born through Culture Discovery.

After the cellar tour, we will participate in a complete tasting of these fantastic wines with dinner in the fabulous tasting and dining room with the owners of the winery. Again, you will have an extremely unique insider experience today, and will learn much more about wine and the business of Italian wines that you ever otherwise could. Dinner will be a specially prepared meal by Enrico’s family at the winery!

Places Cortona; Radda in Chianti
Classes & Experiences

Cooking Class (included) resulting in lunch
App: Eggplant Millefoglie
1st: Homemade Pici Pasta with Fresh Pesto Sauce
2nd: Wood Fire-Roasted Tuscan Chicken and Potatoes
Dessert: Tuscan Crostata with Fresh Marmalade


Breakfast: Buffet at At Palazzo Leopoldo (included)
Lunch: : The meal we prepare in cooking class (included)
Dinner: On the Terrace* at Palazzo Leopoldo (included)

After breakfast at the hotel, we’ll make our way to the Tuscan village of Cortona for a cooking class. Cortona is best known as the setting for the movie, “Under the Tuscan Sun”. You will most certainly recognize the town from the movie, however you will be surrounded by scenery from this movie all week, as we travel through the Tuscan countryside.

Our class is at a private villa on the outskirts of town. Franca and her son, Francesco, will teach us their family-style Tuscan home-cooking from recipes that have been passed down through generations. These are the times we savor at CDV as we get the opportunity to mingle with the locals and share their love and passion of their Italian heritage.

What we’ll be cooking today has as much to do with tradition as it does with good taste!

For our appetizer, we will be making Eggplant Millefoglie, which is a local take on Eggplant Parmesan. For our 1st course, we will be making Pici pasta from scratch with fresh pesto sauce with hand-picked basil. Our main course will be Tuscan Roasted Chicken. This delicious and traditional recipe will be baked in the villa’s centuries-old wood-fire brick oven. Back in the day, the locals would come to the villa for a special feast to celebrate the grain harvest which was vital for the farmers of Cortona.

The Tuscan Crostata we’ll make for dessert is another delicious local favorite. These local miniature pies or tarts will be filled with homemade seasonal marmalade and baked in the wood-fire oven! Yum!

After lunch, we’ll have a chance to walk-it-off as we’ll stroll the town of Cortona. We can do some shopping, or take a short walk to visit “Bramasole”, Francis Mayes’ villa described in the famous book... or “Villa Laura”, the villa that doubled for “Bramasole” in the movie.

After a filling day, we’ll make our way back to Radda in time for some rest before we meet up for dinner on the terrace* of the Palazzo Leopoldo for an Italian version of a “tapas-style” dinner prepared exclusively for our group!

Places Radda in Chianti; Siena
Classes & Experiences

Get up close & personal with Cashmere Goats. (included)


Breakfast: Buffet at At Palazzo Leopoldo (included)
Lunch: : At Vignavecchia Winery (included)
Dinner: Pizzeria in Siena (included)

This morning we stay very close to home, and really slow down the pace. We will visit the Chianti Cashmere Goat Farm. Nora Kravis is an American woman that has lived here for more than 30 years, and has developed this wonderful farm where she produces some of the best cashmere in the world. We'll get to know her goats and learn all about her wonderful cashmere while here.

After the farm, we will stop in at the Vignavecchia winery, which is just 2 minutes away. Instead of visiting a large commercial operation, this visit gives us an example of a more mid-sized winery in the area. We'll have a full wine tasting here with lunch today.

In the afternoon, we will make our way to the magnificent city of Siena. Much like many of our other stops this week, it is another UNESCO World Heritage Site. It’s no wonder, as here, we find an amazing representation of medieval Tuscan architecture and art. With the roots of the city dating back to the Etruscan period, Siena has become a city of distinction and pride. All the residents have personal ties to the 17 Contrade or neighborhoods that make up the teams for the famous Palio horse race that takes place twice a year in the famous main piazza.

We’ll take a guided walk through the city together, visit the amazing Piazza del Campo and beautiful Duomo: The Cathedral of Siena. You will also have some time on your own to stroll through Siena’s historic and beautiful streets and visit local artisan shops and shopping areas.

Dinner tonight is at a wonderful pizzeria just off of Piazza del Campo.

Places Florence; Radda in Chianti, Gaiole in Chianti
Classes & Experiences

See David at the Academia Gallery. (included)
A Local Tuscan BBQ Evening with Singing & Dancing (included)


Breakfast: Buffet at At Palazzo Leopoldo (included)
Lunch: Florence Food Tour (included)
Happy Hour: Italian Appetizers and Wine in Florence (included)
Dinner: Griglata (BBQ) Party at Ultimo Mulino - The Original Village of Chianti Wine! (included)

Florence- Birthplace of the Renaissance, Michelangelo, Dante & The Medici Dynasty.

Welcome to the historic capital of Tuscany! The epicenter of renaissance art and architecture, it’s no wonder that Florence is one of the premier destinations in Italy and the world. From the Uffizi Gallery, the Ponte Vecchio and Pitti Palace, Florence boasts some of the most impressive sites anywhere, leaving visitors and guests bewildered with its splendor and beauty.

Our day in Florence will start with an insider’s food and wine tour with one of Florence’s premier "foodie" guides. We’ll be visiting markets, shops and culinary artisans of some of the best known eateries among the Florentines. We’ll learn about and sample breads, cheeses, salumi and prosciutto. We’ll also be treated to a very special pairing with Tuscan wines, olive oil and balsamic vinegars. The perfect finish to our casual walking tour is at a wonderful artisan Gelato maker and chocolate shop that will leave your tummy and taste buds completely satisfied.

After our gastronomic gallivanting, we’ll be treated to a guided tour of the Galleria dell’ Academia. This world famous museum houses one of the most spectacular marble masterpieces in all the art world - Michelangelo’s David. The museum also houses incredible works by other epic Italian artists such as Botticelli and Giambologna. Another impressive exhibit is that of the Hall of Musical Instruments that has a Stratovarius violin along with a 17th Century Pianoforte designed and built exclusively for the Medici’s. But, the real treat is undoubtedly The David.

After this cultural feast, you can enjoy a couple of hours seeing Florence at your leisure. Your host will be happy to give you some suggestions of some wonderful things to see or do during this time. Such as a visit to the Duomo and Giotto’s Bell Tower. The Ponte Vecchio or Pitti Palace. There is spectacular shopping too! Whether you are looking for artisan leather goods, street markets, high fashion, or touristy trinkets, Florence offers all of that and more! Or, simply relax at a local café and enjoy the beauty around you.

We’ll meet up for some aperitivi (wine and small bites) and hangout with the locals at a fantastic enoteca with spectacular views of the Ponte Vecchio! Before our bus takes us back to Radda, we’ll stop for an incredible Florence photo-op at Piazza Michelangelo.

In the evening, we will be having a "Grigliata" -- A BBQ, Italian Style! This will be a group effort, as all who wish to can pitch in, family style. Some of our guests will help man the grill as we BBQ Tuscan sausage, pancetta and more. We'll have a family-style dinner tonight in the lush gardens or rustic dining room with music under the stars.

Places Castellinuzza; Radda in Chianti
Classes & Experiences

Schiacciata & Chianina Steak Lunch Experience with a family at a small local farm & microwinery. (included)
Cooking Class (included) resulting in dinner
App: Pear and Pecorino Tart Or Chef's Selection
1st: Tuscan Lasagna
2nd: Stuffed Turkey Breast with Local Herbs
Dessert: Cantucci (Tuscan Almond Biscotti) with Vin Santo Wine


Breakfast: Buffet at At Palazzo Leopoldo (included)
Lunch: : At the Family Farm & Microwinery (included)
Dinner: The meal we prepare in cooking class (included)

After last night’s BBQ, we’ll take the morning easy and have some extra time to spend in Radda, enjoy the spa or some of the other amenities at our hotel.

After some well deserved rest, we’ll head up to the tiny little hamlet of "Castellinuzza". Our hosts, Simone and his family, raise Chianina Cows. These are the large white cows used for the “Bistecca Fiorentina”. Arguably considered the best beef steaks in Italy, if not the world! They also have a wonderful boutique Chianti winery here, giving us our fourth winery of the week.

We will get together with the family today and it’s easy to understand how they have become fast friends! This will be a very private and immersive experience that is far away from any tourists or big guided tours! They will also be firing up their pizza oven for us!

For lunch today, we will have freshly baked Tuscan specialty pizza bread called "Schiacciata" that we will be making ourselves in the wood-fired oven. Of course, we'll also be having some Chianina beef grilled on the open flame, as well as a lot of additional seasonal local fare they’ll be preparing for us!

After lunch, we will head back to the hotel for a little rest before our final cooking class of the week, which will result in our farewell dinner.

For our appetizer, we will be making a Pear and Pecorino cheese tart. For our 1st course, we will be making Tuscan Lasagna from scratch. Our main course will be Stuffed Turkey Breast with Local Herbs, and for dessert we will be making Traditional Tuscan Cantucci, which are almond biscotti that we will dip in sweet Vin Santo wine. A fitting ending to another special day.

Places Florence-Peretola Airport (FLR)
Classes & Experiences n/a

Breakfast: Buffet at At Palazzo Leopoldo (included)

Sadly, our week comes to a close this morning. The shuttle leaves Radda at 7:00 AM. We will arrive at the Florence Airport by around 8:15 AM. This will be sufficient time for outbound flights leaving after 9:45 AM.

The Not So Fine Print:

Itinerary Subject to Change

This is a base itinerary, which is subject to minor changes before the vacation begins. Changes may be reorganization of days due to closure and festivals, changes due to weather, or seasonal changes. Additionally, these itineraries are prepared well in advance, and at times there are unexpected closures for various reasons that require us to alter the plans. In the end, our goal is always to make it better for our guests, and when substitutions happen, they are always wonderful.

Menu Variations

The menus listed on the itineraries are subject to change depending on season. We use only fresh ingredients wherever possible, so if we are unable to prepare a certain dish, it will be substituted. Occasionally we make changes to some items as certain dishes prove to be very popular.


Some places on our itineraries don't work well with cold weather or rain. We may have to have some of our meals indoors that were scheduled to be outside. When we do expect rain, we try to rearrange the schedule to make the best of it, but substitutions may be made.