This is an exclusive, all-inclusive week in Chianti, in the heart of Tuscany’s countryside, centered around the grape harvest and the timeless tradition of stomping grapes. We will be staying in a private villa set amid the stunning, breathtaking scenery of San Casciano in Val di Pesa, in Chianti.
Throughout the week, you’ll experience out-of-the-ordinary day trips and excursions that offer an insider’s perspective rarely found any other way. We will visit beautiful hilltop villages, wineries, farmers, and local artisans, sampling their products along the way. You’ll be fully immersed in Tuscany’s country life during one of the most magical times of year—harvest season—when wine, olive oil, and mushrooms take center stage.
Join in the grape harvest, stomp grapes the old-fashioned way, hunt for truffles in the woods, and enjoy hands-on cooking classes using fresh, local ingredients. Drink all the wine your heart desires as we celebrate the flavors, traditions, and rhythms of rural Tuscany.
This adventure is designed for those who want to experience genuine Tuscan life like a local. You’ll have guided time to learn about the area, along with plenty of free time to explore at your own pace.
This intimate experience is limited to just 12 participants.
Benvenuti in Chianti!
We will pick you up in Florence in the late morning and we will head to the Chianti region. We will begin our day by visiting a beautiful wine and olive oil farm. 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 visit an organic honey producer and bee farm in Chianti, where you will be discovering the world of Tuscan bees and their delicious product: honey.
We will take you to the farmhouse in the afternoon, check in and you will have free time to get familiar to your new home for the week, with time for relaxation and to enjoy the magic beauty of our land.
A welcome feast will be served at the farmhouse. Benvenuti!
We will begin our day in a very special way! Today, we will head towards Greve in Chianti for the unique and spceial wine festival “Expo del Chianti Classico!” Expo Chianti Classico represents the privileged opportunity to get to know Chianti Classico wine in its unique production area. The event, organized by the Municipality of Greve in Chianti, is the only one that brings to the square the producers of all the Municipalities of the Chianti Classico. This highlights the importance of the unity of a great territory.
We will then visit a family owned extra virgin olive oil producer in Chianti, 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 experience a gentle and picturesque hike amongst the vineyards and olive groves. On the way, we will learn great stories of our land, and will admire stunning views over the rolling hills. During this light hike, we will able to discover our Tuscan land from another perspective, slowing down and getting closer to the incredible beauty of nature.
Late afternoon of relaxation and dinner back at the farmhouse.
Our day will begin with a visit to the stunning town of Siena, admiring the magical beauty of Piazza del Campo, the Duomo and learning interesting stories about the famous Palio, a charming tradition from Siena that goes back to the Middle Ages.
We will then visit a family owned winery specialized in the prestigious Vin Santo (Holy Wine) dessert wine, with guided visit of the Vinsantaia and the historical cellar followed by a delicious homemade lunch
Afternoon of relaxation and dinner at the farmhouse.
Our journey will begin with an incredible experience, especially created for you to capture the real essence of the harvest season in Tuscany.
Harvest has always been seen as a time of celebration in the countryside: the hard work, the cultivating sacrifices, all those efforts are finally paid off with the growth of grapes and the festive time of wine making.
The experience will begin in the vineyards, learning how to pick the juicy and colourful Sangiovese grapes,. We will then move in the cellar, stomping the grapes like in the old times. Such a unique and fun experience!
The experience will end with a wonderful “pranzo della vendemmia” (harvest lunch) celebrating together this special time of the year.
After lunch, we will visit the beautiful village of Castellina in Chianti, with free time to explore the shops and alleys. We will also visit the gorgeous Medieval town of Monteriggioni, learning fascinating stories of our land.
In the evening, we will enjoy a visit to the stunning Badia a Passignano abbey, a Middle age monastery still belonging to the monks, enjoying a sunset aperitivo in a lovely wine bar with stunning views over the green rolling hills.
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 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 visit a family owned Brunello di Montalcino with guided tour and panoramic wine tasting.
Late afternoon of relaxation at the farmhouse, dinner at the farmhouse.
Cook it, Eat it!
We will begin our day with a fun and delicious hands- on cooking course in a beautiful country home and wine and olive oil farm nestled in the Tuscan countryside. You will learn how to cook a lovely meal in a fun and relaxing atmosphere.
All the ingredients used are fresh, many of them directly from the farm. If the weather allows, the course is held outdoors overlooking vineyards and olive trees. The farm stands on top of a hill in an oasis of peace and tranquility away from noise, cars and pollution. A perfect Tuscan dream!
The class will be completed by a beautiful lunch tasting all the recipes we just prepared.
After lunch we will head to the lovely Chianti village of Panzano in Chianti, learning about the spectacular Golden Valley with its dreamy views. We will also explore the gorgeous hamlet of Montefioralle, awarded as one of the most beautiful hamlets of Italy.
Dinner at out a gorgeous property!
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 a beautiful pottery worshop where you could find unique gifts for family and friends.
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 gelato in the world”.
Late afternoon: time for relaxation at home, dinner will be out at our favorite trattoria in Chianti!
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.
NOTE: As we partner with small, family-run businesses, some flexibility in the above itinerary is necessary. We may adjust the schedule, modify activities, or substitute locations to ensure the best possible experience. A finalized itinerary will be provided two weeks before our adventure begins.
8 Days / 7 Nights
$5,950 USD Per Person for Double Occupancy Room / Single Supplement Not Available for This Tour
$1,000 USD Non-refundable deposit is required to secure your spot.
Francesca Montillo, Native Italian, Owner and Tour Leader Accompanies all Activities. Contact Francesca at francesca@thelazyitalian.com 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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