Chianti, Tuscany

May 6 - 13, 2023

  • 8 days / 7 nights fully inclusive stay in a private villa in Chianti
  • ALL INCLUSIVE: Accommodations, meals, transfers, excursions and activities
  • Visit to organic goat cheese farm
  • Farm visits with local producers and artisans
  • Hands-on cooking classes & demos
  • Pizza & bread making workshop
  • Inspiring walks in Chianti’s nature, ​enjoying the breathtaking scenery
  • Visits to San Gimignano, Siena, Pienza, Greve & Cortona
  • Cashmere goat farm visit with lunch following
  • Visit to pecorino cheese producer with lunch on location
  • Guided truffle hunting experience with lunch following
  • Enjoy small group attention throughout the week

This is an exclusive and all inclusive week in Chianti. We will be staying in a private villa, located in the stunning and breathtaking scenery of Tuscany’s country-side. We will experience out-of-the ordinary day trips and excursions that will give you aninsider’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. 

  • Pizza, focaccia & bread workshop
  • 4 course cooking lesson with Slow-Food movement chef
  • Visit to family-run organic winery with tastings of local products
  • Sunset aperitivo in Badia a Passignano
  • Visit to cashmere goat farm
  • Visit to Siena and tasting of local sweets
  • Pizza party back at the villa
  • Winery visit with tasting and lunch
  • Terracotta workshop visit in Impruneta
  • Cooking and olive oil lesson with Janet & Stefano
  • Visit to Pienza for lesson on pecorino cheese-making
  • Visit to Brunello di Montalcino winery
  • Truffle-hunting experience with truffle-themed lunch following our hunt
  • Tour of San Gimignano
  • Farewell dinner in local trattoria 
  • ​Group transfer from Florence to our villa on day 1, group airport transfer from Villa to airport on last day


  • Airfare / Flights
  • ​Tips / gratuities for guides, instructors and drivers (Appox. 150 USD or Euros for the week)  
  • Villa incidentals such as phone calls, mini bars and other amenities
  • Travel Insurance: As of 2023, we will require everyone traveling with us to carry some form of Travel Insurance. Click here for info.  
  • Anything not listed in the inclusions above

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”

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 - Pecorino Cheese producer in Pienza + Brunello di Montalcino

Visit to Pienza and Montalcino

We will begin our day with a relaxing walk in the beautiful village of Pienza, a marvelous village protected by the UNESCO world heritage sites. We will then visit an awarded organic pecorino cheese maker near Pienza, enjoying a guided tour of his fascinating farm and learning everything you wanted to know about 100% Tuscan Pecorino!

After lunch, we will visit a beautiful and family owned Brunello di Montalcino winery, enjoying a guided tour of the cellar followed by a Brunello wine tasting under their panoramic pergola.

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
$4,700 USD Per Person for Double Occupancy / Single Supplement is $500 USD. (See details above for list of inclusions / exclusions.)
$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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