Tuscany Countryside

May 6 - 13, 2023
2024: 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 Montefiridolfi. 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. We will participate in a gentle hike among the villages of Chianti, only to be refreshed with a stop at a local winery for a light lunch and sample of their wines.  A bread workshop led by a local “panaio” (bread baker) is sure to be a learning and tasty experience! A visit to an artisanal pasta producer with lunch following is also planned for the week! This adventure is aimed specifically at participants who wish to really experience genuine life like a local Tuscan.


  • 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. 
  • 7 Night stay in beautiful agriturismo in 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.
  • Guided visit in the town of Bolgheri
  • 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.
  • Guided visit to Assisi, Umbria’s favorite town and home to the St. Francis Basilica. Enjoy both guided and alone time to explore.
  • 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 - The Experience Begins!

Arrival in Chianti, Bread & Pizza Workshop

Benvenuti in Toscana! Group pick up in Florence for transfer to the beautiful Chianti region, checking in at our beautiful villa, which has been reserved just for us. In the afternoon, 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 served at the farmhouse for dinner, if you still have room!

Day 2 - Four-course Cooking lesson

Learn from a Slow-Food Chef + Organic family run winery visit with sunset aperitivo

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

Cashmere + “Under the Tuscan Sun” Lunch Experience + 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, where we’ll enjoy a real espresso in the stunning Piazza del Campo and 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 Assisi

Cheesemaking Class + Visit to Umbrian Village

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 Assisi, in Umbria. A UNESCO World Heritage Site, Pilgrims have been coming to Assisi for centuries to visit the famed Basilica of St. Francis, walk the streets, tour the many churches, and simply to visit this stunning town.

You will enjoy some guided time, as well as free time there to explore the shops and alleys at your leisure.

Day 5 - Visit to Olive Oil Mill + Visit to Montefioralle

Lunch with Dear friends Stefano and Janet + Cultural Visit to Small Hamlet

Today, we will 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.

Day 6 - A Day at the Tuscan Seaside

Today we visit a different side of Tuscany!

We will begin our day with a relaxing breakfast at the villa. After enjoying a breakfast made by our villa hosts, we will heads towards another part of Tuscany few folks venture out to, the seaside! Yes, Tuscany does have a seaside. After a walk in the gorgeous and panoramic environment, we will feast on a seafood lunch!

After lunch, we will visit the lovely hamlet of Bolgheri in the provence of Livorno. Here we will enjoy a guided walk, as well as some time on your own to shop for souvenirs to bring back to lucky recipients! 

For dinner tonight, we head back to our villa for a delicious meal!

Day 7: San Gimignano and its Treasures

Truffle Experience + Discover San Gimignano

Our journey will begin with a unique truffle hunting experience in the forest with trained dogs and with an experienced local truffle hunter, who will tell us interesting legends and curiosities about this precious gift of 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 village of San Gimignano. This magical location is famously known for its array of medieval towers that can be seen from miles away. We will enjoy a stroll through the traditional shops and streets, and we will also visit an interesting silversmith workshop there, where Matteo, a young and talented silversmith, will show us how he transforms shapeless silver in marvelous objects.

A farewell dinner will be enjoyed at our favorite trattoria in Chianti, tasting 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
2024: This tour is available as a private tour in 2024, please inquire about price and dates.
$1,000 USD Deposit is required to secure your spot. Deposit will be applied towards overall cost of tour.

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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