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8 Days Palio di Siena, Cooking & Wine Tours in Tuscany

Tuscan Cooking Holidays

Just once per year during our regular cooking and wine vacations in Tuscany, we will visit Siena at the famed "Palio di Siena". We will have an insider's experience as we become honorary members of the Onda Contrada, dine with them, root for them, and experience festival life in Italy. Enjoy cooking classes, Tuscan wineries, wonderful sightseeing in Central and Southern Tuscany, and many other exclusive experiences that you can only experience this week. Booking this trip with us includes highly coveted balcony space for the Palio Race!


  • 5 wine tours, 5 wine tastings
  • Cheese tasting, olive oil tasting
  • 3 cooking classes, baking class
  • Excursions in Tuscany, Chianti, Siena
  • Experience exclusive access at Palio di Siena
  • Culture Discovery Vacations apron & recipes
  • 7 breakfasts, 7 dinners, 6 lunches, wines
  • 7 nights accommodation


6 days with instruction in English
Spoken languages: English
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Palazzo Leopoldo

Our home for the week is the beautiful "Palazzo Leopoldo". This ancient Palazzo dates back to the 1400's. A private villa for centuries, the Palazzo was recently restored and converted into a beautiful boutique hotel with just 18 rooms. It features large rooms, beautiful views, and a true small-town Tuscany experience.


  • While small, the palazzo offers most traditional services. Free WIFI throughout, air conditioning, heating, in room safes, hair dryers, laundry service, etc.


The hotel Palazzo Leopoldo receives your guests in elegant bedrooms, Junior Suites and Suites with ancient furniture that witness the splendid past of the manor house, bedrooms with all the comforts, from the satelllite TV to the air conditioning. Palazzo Leopoldo's rooms and suites offer sophisticated elegance in historical ambient, together with original frescoes, cotto floors and fireplaces wide bathrooms with hydro massage shower and a enchanting view on the hills of Chianti.

Wellness Centre

Holidays in Palazzo Leopoldo are made more beautiful by the fitness and wellness area. There is the possibility to have sauna, solarium, wellness treatments, massages and to use the fitness area with gym equipment and the indoor heated pool. Palazzo Leopoldo is glad to make for its guests personalized wellness packages.

The outdoor swimming pool

The guests of Palazzo Leopoldo can, without any extra charge, use the outdoor swimming pool of Ultimo Mulino, 4 stars hotel of Ross Hotels Group that is far from Radda in Chianti only 5 minutes by car. By the swimming pool it is possible to rent towels or to have a delicious snack or lunch by the restaurant of the hotel!

Our story

If you have been reading through Culture Discovery Vacations website, it should be clear that there is a personal story behind everything we do, and this is no exception. It all started when Spartaco and Rocky were scouting the area. They really wanted to put something together here, mostly because this is Spartaco's favorite area of the country.

They happened to meet Massimo, the owner of this and three other hotels in the area, and somehow there was an instant connection. So much so, that when they told Michael about what they had put together, most of their excitement was about Massimo! They said that he was just like us, and asserted that the moment Michael met him, he would be "all in" as well.

This was roughly two years before we launched this new location, and in that time, Michael Did meet Massimo, and Was "all-in" after meeting him. In fact, in that time, a friendship was born that went beyond business. Massimo has been our guest in Soriano and we frequently visit, if for nothing else, just to hang out.

The point is that it is rare to find people that truly share our philosophy. When we do, we need to work with them for the sake of working with them. That is, people that believe that it is about friendships, and passion, and not about money, need to stick together!


Day 1: Saturday

Highlights: Welcome to Tuscany!

Places: Florence Airport; Radda in Chianti

Classes: None

Dinner: at La Loggia del Chianti

Walking on Saturday: On Saturday when you arrive, you will be walking from piazza to the hotel for check in. We will help with your bags if you desire. The total is just about 200 feet (60 meters) on a very slight incline. Dinner tonight will be at a restaurant in town that will be the equivalent of several flights of stairs each way (down on the way to dinner, and up on the way back). Total walking Saturday is about 0.25 miles (0.4 km).

Time in Bus on Saturday: The only time you will be in the bus today is to get to Radda. The drive from the airport is 37 miles (60 km), and should take roughly an hour due to winding roads and traffic.

Welcome dinner menu


  • A sampling of Local Salame & Bruschetta

First Course

  • Panzerotti & Pici Pasta

Second Course

  • Tagliata (Tuscan Steak w/ Balsamic Vinegar)


  • Cantucci (Tuscan Almond Biscotti) that we will dip in sweet Vin Santo wine

Day 2: Sunday

  • Highlights: The Meleto Castle, Chianti Classico & Our First Cooking Class
  • Places: Radda in Chianti; Gaiole in Chianti
  • Breakfast: At Palazzo Leopoldo
  • Lunch: At L'Ultimo Mulino in Gaiole
  • Dinner: The meal we prepare in cooking class
  • Walking on Sunday: There is very little walking today, and no hills to speak of. Total walking today is about 0.25 miles (0.4 km).
  • Time in Bus on Sunday: We'll be staying very close to home today. Each leg of the day is within 10 minutes, for a total of about 35 minutes in the bus today.
  • Rest Time on Sunday: After lunch we will have an hour to an hour and a half o rest at the hotel before our first cooking class begins.

Chianti wine tour #1

We will begin our first full day together with a drive to the nearby Meleto Castle, at the boundary between the ancient Republics of Siena and Florence. It will feel like a like a fairytale as we drive up the cypress lined driveway to this beautiful 13th century medieval castle surrounded by vineyards. The Castle dates back to 1269, having belonged to the Benedictine monks of the Coltibuono Abbey.

After a tour of the castle and the wine cellars, we will be treated to a private wine tasting of several of the wines that come from this property, including their Chianti Classico DOCG.

Cooking class #1


  • Fried Sage

First course

  • Spinach and Ricotta Gnudi

Second course

  • Pork Fillet in Chianti Wine Sauce


  • Limoncello-Raspberry Tiramisu

Day 3: Monday

Highlights: A Day of Wine & Cheese in Southern Tuscany

Places: Montalcino; Montepulciano; Pienza; Radda in Chianti

Classes: None

Breakfast: At Palazzo Leopoldo

Lunch: At Piombaia Winery

Dinner: At De Ricci Winery

Walking on Monday: This is a long day out, with about 1.2 miles (2 km) of walking all day. Most of the walking is during the afternoon in Montepulciano. You will have free time to browse the town on our way to the main piazza. This is about 1/2 mile (0.8 km), which is on an uphill incline. If you prefer not to do this, there is a city bus that will bring you to the piazza. There is also a 0.4 mile (0.6 km) walk after the last winery that is all downhill.

Time in Bus on Monday: This is our longest driving day of the week. The drive to Montalcino is 48 miles (78 km), which will take about 90 minutes in the morning. From there, Pienza is 19 miles (30 km), which will take about 30 min. Next the drive to Montepulciano is 7 miles (12 km), taking about 10 min, and finally the drive home is 49 miles (78 km), which will take about 80 min.

Rest Time on Monday: Today is a full day out. We will not be back in town until after dinner . Most guests take time to close their eyes on the bus ride.

Tuscany wine tours #2

We'll start by driving to our furthest point, the town of Montalcino. To get there, we will be driving the famous Orcia Valley Wine Trail through this picturesque wine region which evokes the classic image of Tuscan rolling hills. This is the area of Tuscany that most of us think of, 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 over a thousand years. They produce only five to eight thousand bottles 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.

We will be hosted to a wonderful lunch with the owners of the estate, as we sample their Brunello wine with our meal. 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.

After lunch, they will treat us to a private tour of their vineyards before we move on.

Cheese tasting

Next, we'll take the short drive to beautiful Pienza, known for its incredible Pecorino cheese. You will have a 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.

Tuscany wine tours #3

Montepulciano is known for its Vino Nobile wine, a primary competitor for the Brunellos. Here we will tour the town's ancient 14th century cellar that was built underneath the Palace of Cardinal Ricci and 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.

As you visit the cellar, you will get a better feeling for how connected Culture Discovery Vacations is to this place, as well as the first 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 at the cellar, and 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.

Day 4: Tuesday

Highlights: The Palio di Siena (Day One)

Places: Radda in Chianti, Siena

Classes: None

Meals: Breakfast: At Palazzo Leopoldo

Lunch: At the Onda Contrada

Dinner: At the Onda Contrada

Walking on Tuesday:

Tuesday will be our first day at the Palio of Siena. It is difficult to say how much walking there will be today, because we have no idea how the festival will play out, or what guests will want to do. That said, assume a couple miles (3 km) of walking, mostly flat today. Also note that this is one of Italy's most popular festivals. It will be very crowded today!

Time in Bus on Tuesday: The drive Siena is 16 miles (26 km), and will take about 40 minutes each way.

Rest Time on Tuesday: This is another full day out, however we get a late start today, and won't be leaving the hotel until around 11:30 AM.

Excursion: Palio di Siena festival

The Palio di Siena is perhaps the most famous of Italian festivals. It is a truly iconic event that has been running since the 1600's. For millions, this is a bucket list event, much like the running of the bulls in Spain.

The "Palio" is a tall banner that serves as the trophy awarded to the winner of a horse race that will take place tomorrow. The race is held in the center of the city in Siena's Piazza del Campo. Riders from 10 of the city's 17 wards (called Contrade) will race bareback around the piazza in an effort to win the highly coveted Palio.

But this event is about much more than a mere horse race. That is simply the main event that is surrounded by one of Italy's most famous festivals. The event is more about the rivalry amongst the contrade, the pageantry, the incredible decor, and life in Siena for centuries. Ask anyone from Siena, and they will tell you that the Palio may only happen twice per year, but they live it every day, all year long.

This festival is very crowded and can be very chaotic. This will be an adventure, and guests that expect order should reconsider. Things will not go as we expect, restrooms will be difficult to find, areas to sit may or may not be easy to find, etc. There will be a good amount of walking, and while we have this itinerary planned out to some degree, it is nearly impossible to how things will actually play out. We will not be able to cater to guest needs while at the festival.

Please note that Onda may not race in this Palio. There are 17 contrade in Siena, and only 10 run the race. If a contrada ran in the last race, they participate in a draw with the other contrade that also ran the last race. The 7 that did not run will automatically run this time. Of the 10 that did run in the last race, 3 are chosen to run this time. Onda most recently ran (and won) the August 2013 Palio, so they will be participating in the July 2014 draw. If they are not selected, we may have some of our meals in other taverns. Whether or not they run, Onda is our contrada, so we still support them and wear their colors!

Day 5: Wednesday

Highlights: The Palio di Siena (The Main Event)

Places: Radda in Chianti, Siena

Classes: None

Breakfast: At Palazzo Leopoldo

Lunch: At The Onda Contrada

Dinner: At the Onda Contrada

Walking on Wednesday: Our second day at the festival will be much like the first. It is difficult to say how much walking there will be today, because we have no idea how the festival will play out, or what guests will want to do. That said, assume a couple miles (3 km) of walking, mostly flat today. This is the main day of the Palio, so it will be even more crowded today!

Time in Bus on Wednesday: The drive Siena is 16 miles (26 km), and will take about 40 minutes each way.

Rest Time on Wednesday: This is another full day out, however we get a late start today, and won't be leaving the hotel until around 11:30 AM.

Excursion: Palio di Siena festival

Today will be even more chaotic than yesterday! We cannot stress enough that guests wishing to come for this week are prepared. The crowds will be massive and disorderly. We have no way of knowing what to expect today, so you must have a sense of adventure.

Day 6: Thursday

Highlights: The Chianti Cashmere Farm, Vignavecchia Winery & The Grigliata!

Places: Radda in Chianti; Gaiole in Chianti

Breakfast: At Palazzo Leopoldo

Lunch: At Vignavecchia

Dinner: The Grigliata

Walking on Thursday: When we visit the cashmere farm, our mini bus may not be able to get all the way there. If this is the case, we may need to walk about 0.25 miles (0.4 km) each way. Other than that, there is very little walking today.

Time in Bus on Thursday: There is very little time in the bus today, with a total of about 20 minutes.

Rest Time on Thursday: Today is a quite relaxing day. After lunch, we have a couple hours of relaxation time at the hotel before the Grigliata.

Baking class


  • Tuscan Biscotti & Tartufo

Day excursion: 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.

Wine tasting #4

After the farm, we will stop in at the Vignavecchia winery, which is just 2 minutes away. The Meleto winery we visited a few days back was a good example of a larger, more commercial winery of the Chianti region. This gives us an example of a more mid-sized winery in the area.

Day 7: Friday

  • Highlights: Greve in Chianti, Schiacciata & Our Final Cooking Class
  • Places: Greve in Chianti; Castellinuzza; Radda in Chianti
  • Breakfast: At Palazzo Leopoldo
  • Lunch: At Castellinuzza e Piuca
  • Dinner: The meal we prepare in cooking class
  • Walking on Friday: There is not much walking today, except what you do on your own in Greve, which is completely flat. Estimate roughly 1/2 mile (0.8 km) today.
  • Time in Bus on Friday: There will be about a total of 1 hour in the bus today, half hour each way.
  • Rest Time on Friday: After lunch, we will have about an hour and a half of rest time at the hotel before our cooking class.

Day excursion: Greve in Chianti

Greve in Chianti is a great little town with a large piazza, full of excellent shopping. Being the final day of the week, we have set aside a couple hours today give everyone time to get some shopping and browsing in on their own.

Tuscan wine tours #5

As we leave Greve, we will head up to the tiny little hamlet of "Castellinuzza". Just two families live in this little hamlet, and they are the Tuscan answer to the Hatfield's and the McCoys! We'll be spending the afternoon with one of the families. Here, they raise Chianina Cows. These are the cows used for Florentine Steak, considered the best in Italy. They also have a tiny little winery here, giving us our fifth winery of the week.

Cooking class #3


  • Pear and Pecorino Tart

First course

  • Tuscan Lasagna

Second course

  • Stuffed Turkey Breast with Local Herbs


  • Cantucci (Tuscan Almond Biscotti) with Vin Santo Wine


The Palazzo Leopoldo is right in the heart of Radda in Chianti, on the main pedestrian road, just a few steps away from the Piazza. The location just couldn't be better, as you step out the front door and find yourself on the main "corso" of this darling little Tuscan village with shops, cafes, etc. Radda is a Tuscan hill town. There are moderate inclines while walking in town. The town is very small, but being on a hill, there will be some up and down, as well as stairs as you explore the town.



  • Fitness center
  • Gym
  • Indoor swimming pool
  • Massage
  • Outdoor swimming pool nearby
  • Sauna


  • Bar nearby
  • BBQ facilities
  • Caf nearby
  • Concierge desk
  • Garden
  • Lobby
  • Multilingual staff
  • Restaurant
  • Terrace


  • ATM/banking nearby
  • Free! WiFi
  • Laundry
  • Room cleaning
  • Shop nearby
  • Tour assistance


We are all about food & wine, and if there is one comment we hear more than any other from our guests throughout the week, it is "I can't eat another bite". You will never be hungry, and you will never want for more wine, period.

All of the restaurant meals are in small, local restaurants that are considered the best of the best for their area. These are the places the locals rave about, not the touristy places. Furthermore, we don't do "tourist food". We insist on the highest quality at all times, and always pull out all of the stops.

The wine is always flowing at lunch and dinner. We always focus on local wines from the area we are in, and it is always fantastic! Additionally, the meals at our cooking classes are not little 'learn to make pasta' classes like many others. Instead, the classes are traditional Italian 'Sunday Family Meals' 5 courses, done to the max.

When the week is over, you will have experienced the real Italy that few tourists have ever experienced. You will have made new friends, and you will have learned why Italian culture is so amazing, because you will have lived it!

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