Tuscan Countryside

Fall 2024 Dates Coming Soon!
Also Available as a Private Tour for 6 or more Travelers

This is an exclusive and all inclusive week in Chianti, Tuscany’s countryside. We will be staying in a private villa, located in the stunning and breathtaking scenery of San Casciano in Val Di Pesa, in Chianti. We will experience out-of-the ordinary day trips and excursions that will give you an insider’s perspective not typically found any other way. We will visit beautiful hilltop villages, wineries, farmers and local artisans and sample their products. You will be fully immersed in Tuscany’s country life. Fall is a beautiful time to visit Tuscany for its wine, olive oil and chestnuts. A bread workshop led by a local “panaio” (bread baker) is sure to be a learning and tasty experience! Hunt for truffles in the woods, and enjoy hands-on cooking classes. Drink all the wine your heart desires during the week! You’ll even be making your own wheel of Tuscan pecorino cheese to bring back to the States! 

This adventure is aimed specifically at participants who wish to really experience genuine life like a local Tuscan. You will have guided time to learn all about the area, but also plenty of unguided time to explore on your own. 

This adventure is limited to 12 participants.


  • This is an all-inclusive week. All meals, private transportation, entrance fees, tours, excursions, cooking classes, winery visits and local wine with every meal are included. 
  • 8 days / 7 night in beautiful agriturismo with stunning views, amazing rooms, and gracious hosts
  • Chianti Classico winery visit, tour, tasting with lunch on location
  • Pizza and focaccia workshop with pizza party following
  • 4-Course Cooking class with Chef Rosanna, with lunch on her property
  • Organic wine and olive oil farm visit with tasting of wine and local products
  • Evening stroll in Badia a Passignano with sunset dinner overlooking the majestic vineyards of Tuscany
  • Visit to a cashmere goat farm with local celebrity Nora Kravis. Lunch on her property.
  • Afternoon guided visit of Siena with some time on your own for shopping and exploring
  • Visit the gorgeous Tuscan seaside (yes, Tuscany has a seaside) feast on a seafood lunch enjoying the panoramic restaurant.
  • Visit to Impruneta to discover the local terra cotta
  • Visit to olive oil farm with large lunch following on their property
  • Visit to the lovely hamlets of Montefioralle and Greve in Chianti
  • Make your own wheel of pecorino cheese with our friend Ilaria. Enjoy lunch on the farm afterwards.
  • Truffle hunt in the woods of Certaldo, with local a feast at lunch afterwards.
  • Guided and alone time in San Gimignano
  • Group transfer from Florence to our villa on day 1, group airport transfer from Villa to airport on last day


  • Airfare / Flights (Folks should fly into Florence Airport). 
  • ​Tips / gratuities for guides, instructors and drivers (Appox. 150 USD or Euros for the week).  
  • Travel Insurance: As of 2023, we will require everyone traveling with us to carry some form of Travel Insurance. Click here for info.  

Day 1 - Let Your Tuscan Adventure Begin!

Benvenuti in Toscana!

Group pick up in Florence for transfer to the beautiful Chianti region. On our way there, we will be enjoying a lovely lunch at a family winery, enjoying a guided tour through the farm and cellar, followed by a delightful lunch paired with local wine.

In the afternoon, we will check in at our agriturismo, which has been all reserved just for us. After some time to unpack, we will participate in a delicious and fun bread making culinary workshop with Beppe at the farmhouse, learning the art of making delicious bread, focaccia and pizza. Beppe “Il Panaio,” is a trusted baker and bread expert. Together, we will learn about different kinds of flours and the characteristics of the ancient grains. We will then enjoy a bread-making demonstration, where we will get to see how delicious bread, pizza and focaccia are made.

A welcome culinary feast will be served at the farmhouse. We will be enjoying all kinds of pizzas, paired with Chianti wine, of course!  

Day 2 - Hands-On Cooking Lesson + Winery Visit + Dinner with a View

Today, we will spend a delicious morning, experiencing a hands-on cooking class with Rosanna, a Slow Food Movement Tuscan chef based in the Chianti Classico area. Rosanna’s cooking lessons are fun, educational and interesting. She uses only the freshest and best ingredients and she is a member of the Slow Food Movement. Her hands-on cooking lesson will guide us through the preparation of an entire meal from antipasto to dolce, and ends up on an elegantly decorated table, enjoying the lovely meal we have just created.

After lunch, we will enjoy a relaxing walk in charming Montefioralle, awarded as one of the most beautiful villages in Italy, with time for relaxation and to enjoy the stunning views.

On the way back to the farmhouse, we will stop at a beautiful family-owned organic winery. Enjoy a guided tour through the vineyards and the cellar with tasting of products. Our hosts will be welcoming us into their vineyards, where we will see an organic and passionate approach to wine and farming.

In the evening, we will enjoy a visit to the stunning Badia a Passignano abbey, a Middle age monastery still belonging to the monks, enjoy a sunset aperitivo in a lovely wine bar with stunning views over the green rolling hills!

Day 3 - Under the Tuscan Sun Experience + Visit to Siena

Our day begins with a visit to a unique Cashmere goat farm in Chianti, where we will learn everything we wanted to know about cashmere! Learn about the habits of cashmere goats, their names, how they are raised, how their lovely fiber is harvested and how it is processed into a finished garment. For those who love animals and incredibly soft and pure cashmere, this is going to be an amazing experience. We will have a guided tour of the farm, followed by a perfect lunch experience.

After lunch we will head to the stunning town of Siena. Enjoy both guided and unguided time on your own in one of Tuscany’s most beloved towns. Grab a gelato in Piazza del Campo or taste the “Senesi,” a delicious traditional sweet of this town. We will also have the possibility of admiring the majestic beauty of the Duomo and to learn interesting stories about the famous Palio, a tradition from Siena that goes back to the Middle Ages.

A delicious dinner will be enjoyed at the farmhouse.

Day 4: The Art of Pecorino + Visit to Cortona

We will begin our day with a visit to a wonderful family owned cheese farm in the Tuscan countryside overlooking the gorgeous town of Cortona. We will enjoy a fun hands on cheese making class, learn how to make the freshest ricotta, raviggiolo and pecorino cheese with the cheesemakers Lapo and Ilaria. Will follow a delicious cheese-themed lunch with homemade pasta and other specialties paired of course with locally made wine.

After lunch, we will head towards the stunning town of Cortona, where the famous movie “Under The TuscanSun” was filmed. You will enjoy free time there to explore the shops and alleys.

On the way back to the farmhouse, if time allows, we will stop for a beautiful and relaxing stroll along the beautiful Lake Trasimeno.

We will return to the farmhouse in the evening to enjoy dinner at the farmhouse.

Day 5 - Lunch on an Olive Oil Farm + Visit to Montefioralle

We will begin our day with a visit to a unique terra cotta kiln in Impruneta, seeing how artisans shape beautiful jars and pots.

We will then visit a family owned extra virgin olive oil producer in Chianti, enjoying a guided your of the farm and learning everything you wanted to learn about high quality extra virgin olive oil. The guided tour will be followed by a perfect lunch experience, sampling delicious specialties all paired with olive oil, enjoying time with this lovely family. 

After lunch, we will enjoy a lovely walk in the beautiful villages of Montefioralle, awarded as one of the most beautiful villages of Italy, and in Greve in Chianti, with time to enjoy the beautiful shops. 

Return to the farmhouse in the late afternoon, time forrelaxation and to enjoy the grounds.

Day 6 - The Val D'Orcia Experience: Pecorino Cheese and Brunello Wine

We will begin our day with a relaxing walk in the beautiful village of Pienza, a marvelous village named on the list of by the UNESCO world heritage sites.

We will then visit an organic pecorino cheese maker near Pienza, enjoying a guided tour of this fascinating farm and learning everything you wanted to know about the 100% Tuscan and famous Pecorino!

The experience will be completed by a cheese-themed lunch with a stunning view on the Val D’Orcia Valley.

After lunch, we will enjoy a visit to family owned Brunello di Montalcino wine producer, the most prestigious and well known wine of Tuscany. We will first enjoy a guided tour of the cellar, getting beautiful insights and tasting the classic Brunello wines.

Late afternoon of relaxation at the farmhouse, dinner at the farmhouse.

Day 7: Truffles, Pottery and More!

Our journey will begin with a unique truffle hunt in the forest with trained dogs and with an experienced local truffle hunter, who will tell you interesting legends and curiosities about this precious gift of the nature. 

The experience will start in the fields and will end up in their kitchen, understanding all the secrets and best culinary recipes with fresh truffles. 

After lunch we will enjoy a relaxing walk in the medieval castle of Certaldo, stopping at a beautiful pottery workshop where you could find unique gifts for family and friends.

After lunch we will enjoy a relaxing walk in the medieval village of San Gimignano which is famous for its multiple medieval towers. After we arrive, you can drift off with plenty of free time to enjoy the traditional shops and taste the “best ice-cream in the world.”

Late afternoon is time for relaxation at home. Dinner out in our favorite trattoria, trying the BEST homemade pasta you’ve ever had!

Day 8 - Check-Out & Return to Florence

After breakfast at the villa, we say our good-byes and reflect on the beautiful week we just experienced. Group airport transportation will be provided.

Price & Details

8 Days / 7 Nights

Email Francesca for pricing and images of the property.

Francesca Montillo, Native Italian, Owner and Tour Leader Accompanies all Activities​​. Contact Francesca at for booking/reservation and further details.

If you would like to reserve a spot for this tour, or have any questions, please use the contact form below and we will send you the necessary booking instructions or additional information.

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