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 Ristorante Il Girarosto (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 "Il Girarosto Restaurant". 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 a zucchini carpaccio in a local mint oil and peanut sauce. This will be followed by a 1st course of a Tortelli pasta in local sauce. Our second course will be of several grilled select cuts of meat. For dessert, we’ll have a very traditional local favorite, Cantucci which is the Tuscan-style of Almond Biscotti and a sage cream. 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 lunch
App: Sausage and Stracchino Cheese Bruschetta
1st: Ricotta Gnudi in butter and sage saute'
2nd: Ossobuco alla Toscana
Dessert: Almond Cantucci Biscotti
Wine Tasting Class with Sommelier (included)


Breakfast: Buffet at At Palazzo Leopoldo (included)
Lunch: : The meal we prepared during cooking class. (included)
Dinner: At the Ristorante La Perla in Radda (included)

Our first full day in Tuscany, we’ll enjoy the morning relaxing at breakfast at our beautiful hotel and the town of Radda. You’ll quickly become accustomed to the charm and beauty of the surroundings of this Tuscan town with spectacular vistas of the Tuscan hills.

It's a Sunday and we're going to need to start preparing our traditional Italian Sunday meal! We'll head back to the Il Girarosto restuarant for our first cooking class with our chef instructor, Simonetta. She is a local Tuscan nonna that not only loves to cook, but loves to show people how she prepares everything the way she was taught by her nonna!

Our lunch is a full four course meal that will result in today's lunch, and it is all based on local Tuscan specialties. As always, class is 100% hands-on, so we'll get right into it!

For our appetizer, we will be making a sausage and stracchino cheese bruscetta. Our first course will be a Ricotta Gnudi seasoned in a butter and sage saute'. Gnudi is a Tuscan dish similar to Gnocchi, but made with ricotta! For our second course, we will be preparing Simonetta's Ossobuco. Braised beef shanks made with a Chianti wine sauce. For a side dish, we'll prepare a delicious caponata made from locally-sourced vegetables. Finally, for dessert, we will make her Almond Cantucci Biscotti.

Once class is over, we will sit down and enjoy the meal we prepared together for our lunch in this fabuluos and picturesque setting!

After lunch, we will have a little time to rest at the palazzo before we meet up for our sommelier class and wine-tasting experience. For those of you that are interested, the hotel offers spa services and massages. This could be an ideal time to take advantage of some down time during the week. The hotel front-desk can help you with your advanced spa-services bookings.

We'll meet up again around 6 pm to begin our oenological journey at the Enoteca del Palazzo 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 have dinner, and more wine, at the Ristorante La Perla, in Radda.

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: Charcuterie and Mixed Bruschetta with Faggiolini del Trasimeno
1st: Homemade Gnocchi with Garden-Fresh Tomatoes and Tuscan Pecorino Cheese
2nd: Tuscan-Style Chicken alla Cacciatora
Dessert: Tuscan Crostata with Fresh Marmalade


Breakfast: Buffet at At Palazzo Leopoldo (included)
Lunch: : The meal we prepare during cooking class (included)
Dinner: Italian-Style tapas at a local trattoria (included)

After breakfast at the hotel, we’ll make our way to the countryside not far from 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 estate of our friend, Patrizia and her family. They run a local farm that specializes in growing nearly everything from wheat to vegetables, with a distinct focus on beans and other legumes. All the essential ingredients used in our class will have come from their land. They 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.

The setting of the villa couldn't be more picturesque, complete with quintessential views of the sweeping Tuscan countryside and surrounding hills. What we’ll be cooking today has as much to do with tradition as it does with good taste and sourcing their local production of the freshest ingredients grown in their fields.

For our appetizer, we will be making some mixed bruschetta with a legume-inspired topping, fagiolini del Trasimeno, along with some assorted charcutterie. For our 1st course, we will be making gnocchi from scratch with farm-fresh tomatoes and Tuscan Pecorino cheese. Our main course will be Patrizia's Tuscan Chicken alla Cacciatora. This delicious and traditional recipe will be slow-roasted to perfection. History tells us that locals would come from surrounding villages for a special feast of these same types of recipes 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!

We'll all sit and enjoy our lunch "al fresco" under the oaks of their villa. This is one of those "ahhhhhhhhhh-take-it-all-in" moments that will leave an indelible mark etched into your memory.

We're quite confident that you probably will not want to leave this beautiful setting, however, we must. But, like everything else this week, one great thing leads to another one! So...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 our dinner at a local trattoria for an Italian version of a “tapas-style” dinner prepared exclusively for our group!

Places Radda in Chianti; Siena
Classes & Experiences

Get an in-depth look at life with these special breeds of goats. (included)


Breakfast: Buffet at At Palazzo Leopoldo (included)
Lunch: : At Poggerino Winery (included)
Dinner: Pizza, Sides and Salads (included)

This morning we stay very close to home, and really slow down the pace. We will visit a Chianti Goat Farm. We'll get to mingle with the kids and see how the family raises them and then produce some fantastic cheeses from goat milk.

After the farm, we will stop in at the nearby Poggerino winery. 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 the winemaker as well as lunch overlooking the vineyards, countryside and surrounding valleys. This is another fantastic moment whereby we have an exclusive, up-close and personal experience at a family-run winery with direct access to the owner and winemaker.

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 on our return drive to our hotel in Radda.

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

Michelangelo's David at the Academia Gallery. (included)
An evening of singing and dancing with friends and family at a small local farm & microwinery where have a Tuscan-style BBQ and dine on Grilled Bistecca Fiorentina, Schiacciata and more! (included)


Breakfast: Buffet at At Palazzo Leopoldo (included)
Lunch: Florence Trattoria (included)
Dinner: Griglata (BBQ) Party at a Family-Run Chianti Winery (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 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, we'll continue with a guided city tour that covers many of the highlights of the city, including the Duomo, Battistero, Giotto's Tower, Piazza Signoria and the Palazzo Vechhio. After this, we'll have worked up an appetite. Time for lunch at a wonderful trattoria nearby.

After lunch, take some time on your own to 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.

It's not uncommon for many of our guests to meet up with the tour host for some aperitivi (wine and small bites) and hangout while waiting for the other guests who may still be out shopping or site-seeing.

After this fantastic day in Florence, more fun awaits as we head out to a small Tuscan "borgo" to a family-run winery and farm. 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 have a tour of their winery and cantina, just before we get together with the family and relax and settle into the evening. After a very short time, it becomes very evident and 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! Here, we'll be having a "Grigliata" - A BBQ, Italian Style!

For our dinner this evening, we will have freshly baked Tuscan specialty pizza bread called "Schiacciata" that we will be making ourselves and putting in the wood-fired oven. Of course, Simone will be "Q-ing" up the grill and prepare their tender and delicious Chianina beef grilled on the open flame, just however you like it! There will also be a lot of additional seasonal local fare they’ll be preparing for us! And their fabulous wines, of course!

As the evening progresses, it becomes more of a festive party atmosphere as music starts playing, everyone startes dancing and singing many their favorite songs and living La Dolce Vita! This is surely going to be a night to remember!

Places Radda in Chianti, Gaiole in Chianti
Classes & Experiences

Cooking Class (included) resulting in lunch
App: Plum and Almond Pancetta Roll on Artisanal Bread
1st: Lasagna alla Toscana
2nd: Vin Santo Wine-Infused Braised Pork Spezzatino
Dessert: Simonetta's Caprese Cake in Orange Sauce


Breakfast: Buffet at At Palazzo Leopoldo (included)
Lunch: : The meal we prepare during cooking class. (included)
Dinner: A Specially-Prepared Farewell Dinner at The Ultimo Mulino (included)

After breakfast, we'll be heading back to Il Girarosto for our final cooking class with Simonetta.

Today, we'll be preparing a full-course lunch that begins with a plum, almond and pancetta roll that will be served with an artisanal and local black bread. The first course will be lasagna, Tuscan-style! This dish originates from nearby Emilia Romagna, and this is another delicious local version, just the same! Our second course will be a slow-roasted braised pork stew, known locally as spezzatino. This dish is prepared using Vin Santo wine, giving it a rich and distinctive depth of flavor. If that isn't enough, we'll also be making a "chef-favorite" Caprese Cake in an orange sauce. This is a family recipe that Simonetta loves to share with all our guests!

Of course, everything will be amazing and delicious and we'll enjoy our lunch together in the atrium room.

After lunch, you'll have some time to relax before we head out in the evening. This is an opportunity to rest up, take a stroll through Radda, or use the spa at the hotel. Reservations for any personal services should be scheduled well in advance.

Tonight's traditional Farewell Dinner will be at a unique setting in the nearby village of Gaiole in Chianti. The building was originally a 15th century water-mill that was used by the local community to channel water flow to fields and towns in the area. The building has been completely restored and converted into a boutique hotel and restaurant with a lot of charm as well as historical relevance as many of the features from the mill have been incorporated into the current architecture and design elements.

The chef will prepare a special menu exclusively for our group. We'll be treated to some wonderful appetizers other local fare as we relax with some wine, share photos and reminisce about the amazing week we all just had!

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 by 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 10:00 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.