Fall in Tuscany's Countryside

October 12 - 19, 2024 (Sold Out)
October 4 - 11, 2025 (Sold Out)
October 18 - 25, 2025

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! 

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 unlimited local wine with every meal are included.
  • 8 days / 7 night in beautiful villa with stunning views, amazing rooms, private bathrooms and gracious hosts.
  • Guided visits to: Siena, San Gimignano, Panzano, Castellina in Chianti, Greve, Monteriggioni, Marradi and Certaldo.
  • Chianti Classico winery visit, tour, tasting with lunch on location.
  • Pizza and focaccia workshop with pizza party following, enjoy unlimited pizza.
  • Hands-on saffron themed cooking class  with lunch on the property.
  • Visit and guided tour of a special winery that produces Vin Santo, Italy’s Holy Wine. Enjoy lunch on the property afterwards.
  • Attend the world famous annual chestnut festival in Marradi. Enjoy samples and an ample lunch on location.
  • Visit a pasta producer and learn all about Italy’s most iconic ingredient.
  • Visit an olive oil farm, meet our friends Janet and Stefano, and enjoy a gourmet lunch on their property.
  • Head into the woods with our favorite truffle hunter, Luigi. Learn all about one of the world’s most expensive ingredient and enjoy a truffle-themed lunch afterwards.
  • Visit to a pecorino cheese farm, and enjoy a cheese-themed lunch afterwards.


  • Airfare / Flights (Folks should fly into Florence International Airport).
  • Transfer from airport to Florence upon arrival.
  • Tips / gratuities for guides, instructors and drivers 
  • 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!

Welcome to Tuscany! Enjoy a Full Lunch on a Winery, plus a Pizza Workshop

Benvenuti in Toscana!

Our day begins in Florence in the late morning where you will be picked up in our private vans and we will head to the countryside area of Chianti. We will stop for lunch along the way at a family-owned winery. Here, we will enjoy a guided tour through the farm and the cellar followed by a delightful homemade lunch sampling the real “cucina chiantigiana.

After lunch, we will check in at the villa, where you will meet our lovely hosts Massimo and Miranda. Get familiar with your new home for the week, with time for relaxation and to enjoy the magic beauty of our land.

In the later afternoon we will enjoy a delicious and fun bread culinary workshop with Beppe, learning the magic art of making delicious Tuscan bread, focaccia, and pizza. Beppe is our trusted baker and local bread expert. Together with him, you will learn about the different kinds of flours and the characteristics of the ancient grains. You will then enjoy a bread making demonstration, where you will get to see how delicious bread, pizza and focaccia are made.

You’ll enjoy a welcome pizza party afterwards with all-you-can-eat pizza and wine!

Day 2 - Chestnut Festival in Marradi + Discovering the Unexplored Mugello Area of Tuscany

Enjoy a Visit to Undiscovered Marradi for the Yearly Chestnut Festival

Get ready for a wonderful experience, as today we will be heading to the unexplored area of Marradi to attend an amazing chestnut festival! Marradi is a lovely mountain village in the Mugello area north of Florence, and every Sunday in October they host a wonderful chestnut festival!

It is the most historic and important chestnut festival in all of Italy. Marradi is known for its marrons glaces (candied chestnuts), and October is the season they are celebrated. This local festival is full of food stands offering all the best local products and traditional food based on their prized chestnuts. We will enjoy a love walk at the festival, with some free time to explore the food stands and to wander in the village on your own to shop for souvenirs. We will also enjoy a fabulous lunch at the sagra, with plenty of food and specialties.

We will return at our home base in the late afternoon and enjoy dinner prepared by our hosts.

Day 3 - Saffron Inspired Hands-On Cooking Class + Visit to Panzano and Castellina in Chianti

Grab Your Apron for Our First Hands-On Cooking Class

The day begins with a fun and delicious hands-on cooking course in a beautiful country home nestled in the Tuscan countryside. You will be learning how to cook a lovely full meal all based on the prestigious saffron, using the host’s own production of postils. From the pasta course to dessert, you will fall in love with saffron today as we use all fresh ingredients, many of them directly from the farm. As a bonus, if the weather permits, we will hold the course outdoors, overlooking the vineyards and olive trees. The farm stands on top of a hill, an oasis of peace and tranquility. A perfect Tuscan dream!

After lunch, we will explore the lovely villages of Panzano and Castellina in Chianti, getting lost in incredible views and enjoying plenty of time to explore the alleys and shops.

Dinner tonight will be at one of our favorite Tuscan spots.

Day 4: Siena + Vinsanto Winery + Monteriggioni

Enjoy a Special Visit to a Vinsantaio, Plus Visit Undiscovered Hamlets

Our journey today begins with a visit to the stunning town of Siena, admiring the spectacular beauty of Piazza del Campo. Admire the majestic beauty of the Duomo and learn from our licensed guide the fascinating stories about the famous Palio, a charming tradition from Siena that goes back to the Middle Ages.

We will then enjoy a visit to a family-owned winery that specializes in the prestigious Vin Santo (Holy Wine) dessert wine, with guided visit of the Vinsantaia and the historical cellar followed. A delicious homemade lunch with tasting of wines in front of an incredible view awaits us.

After lunch, we will head to the beautiful medieval castle of Monteriggioni, learning interesting stories of this town and enjoying free time to enjoy the shops and gorgeous piazza.

We will return to our home base for dinner tonight.

Day 5 - Artisanal Pasta Workshop + Olive Oil Experience with Harvest Lunch + Chianti Villages

We're in Fall, so Time for the Olio Nuovo! Plus a Lunch to Remember.

We will begin our day visiting an artisanal pasta workshop in Chianti, learning everything you always wanted to know about one of the most important icons of Italian cuisine!

We will then visit our dear friends Janet and Stefano, who are extra virgin olive oil producers in Chianti. Enjoy a guided tour of the mill and learn everything you wanted to learn about high quality extra virgin olive oil. A perfect lunch experience sampling delicious specialties all paired with olive oil is sure to follow. You’ll love spending time with this lovely family.

After lunch, we will visit the lovely village of Greve in Chianti, with free time to enjoy the beautiful shops and piazza, and to another small hamlet, Montefioralle.

Apericena tonight will be at another favorite spot. Wait until you see the views!

Day 6 - Truffle Experience + Discover Certaldo and San Gimignano

Everyone's Favorite Activity is Today! Time to go Hunt for Our Lunch!

Always a group favorite, our journey today begins with a unique truffle hunt in the forest with trained dogs, and with our dear friend Luigi, a local truffle hunter. Luigi will tell us interesting legends and curiosities about this precious (and expensive) gift of nature. The experience will start in the fields and will end in the kitchen, where you will sit down to enjoy a full meal, sample the truffles, and finish with Tuscany’s best panna cotta. 

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

Later in the afternoon we will visit the 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 visit the traditional handmade shops that sell leather, pottery and of course, foodie gifts. If you still have room, visit Gelateria Dondoli, which has been named to have the best gelato in the world.

Dinner tonight will be out, where you will enjoy some of the best homemade pasta you’ve ever had!

Day 7: Pecorino Cheese Farm + Volterra and the Alabaster

Say Cheese! Enjoy the Best Sheep's Cheese Milk this Side of Tuscany!

We begin today with a visit to a wonderful cheese farm in the Tuscan countryside. Get your camera ready as the views on the property are some of the best from all over Tuscany! After a tour of the farm, a delicious cheese-tasting and cheese-themed lunch with homemade specialties will follow. 

Walk off lunch at the magnificent medieval town of Volterra. Along the way, we will stop at for a stunning picture at the famous sculpture called “The Ring” created by the artist Staccioli. This will be a frame-worthy picture for sure! In Volterra, we will explore the charming alleys and visit a historical Alabaster workshop.

A festive farewell dinner prepared by our hosts awaits us tonight as we celebrate our week together. 

Day 8 - Check-Out & Return to Florence

Time to Say Ciao to Toscana

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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