Sunrise in Tuscany, Italy
Il vino è un composto di amore e luce – Wine is made of love and light [Galileo Galilei].


For Tuscany, wine is culture, family, and land, a fundamental part of the history of the entire region. The best way to understand this bond is to just dive into it. Join us on this exploration of Italian language, wine, and culture. Gain insider perspectives from local wine experts and network with industry professionals and wine enthusiasts!

All levels of Italian welcome, even beginners.

Location: Tuscany, Italy
Price: $6,100-$6,900 (airfare not included)
Register/Questions: To register or for any questions, please email Alicia Brent at
Date: Monday, September 19, 2022, to Saturday, October 1, 2022

Registration Deadline: June 30, 2022


Our 12-day adventure begins in the historic city of Florence, where we will spend four days and five nights immersed in its language, history, and culture as we gain unique perspectives on this “pearl of the peninsula.” We will then journey through the Tuscan countryside south toward Siena where we will stay for one week in a 14th century villa owned by one of Tuscany’s oldest and well-known families. As we explore the Tuscan countryside, we will be guided by some of the region’s most knowledgeable experts in Italian wine, its traditions, evolution, and the industry that supports it today. 

*The Italian language component of the program will be limited to the morning sessions while in Florence, but opportunities to engage with locals and practice your Italian are unlimited throughout the experience!  

Florence, Italy skyine at dusk.
Arches in a cathedral in Florence


In Florence, you will explore the essence of Florentine culture through a combination of Italian language classes and cultural excursions along with insights about the wine tradition of the region given (in English) by Italian faculty from the University of Florence’s School of Viticulture and Oenology. Together we will explore the evolution of the wine industry in the region and the trends that will influence the future of wine production across Italy. 

The language and culture classes, a blend of English and Italian, will be centered around wine and food vocabulary and expressions with a special focus on how food and wine have been depicted through Italian art over the centuries. Silvia, an art historian with a special interest in Italian food history, will walk you through the streets of Florence providing a unique view of its cultural heritage from the Roman times until the modern era. During these sessions, you will also taste wines from the various regions, pair them with the local cuisine, and learn how to talk about them in Italian!


Top of a cathedral in Florence, Italy with clouds and sky in the background.


  • Communicate with locals in Italian! Spend your mornings in Florence learning to talk about Italian wine, food, art, and culture at Middlebury’s renowned language school in Sede Capponi. *We can accommodate those with different levels of Italian, including beginners.
  • Gain new perspectives from local experts: Faculty from the University of Florence will share their knowledge of the traditions and current innovations of the Italian wine industry providing an in-depth understanding of the unique characteristics and production of wine across the different regions. 
  • Experience Italy’s cultural heritage with professors of Florentine art and history as you discover some of the lesser-known stories from the birthplace of the Renaissance.
  • Travel through time as you experience the treasures of the House of Medici and learn about its powerful influence on modern Italy.
Tuscany town skyline
Grape fields in the Tuscan countryside on a sunny morning.

The Tuscan Countryside and Siena

From Florence, the group will travel through the beautiful countryside of Tuscany, south toward Siena, to an impressive 14th century villa that will be our home for the week. There, we will meet the owners of the villa from the well-known Guicciardini family, whose history in the region goes back centuries. The villa is conveniently located near Siena, San Gimignano, and Val d’Orcia, offering the opportunity to visit several of UNESCO’s World Heritage sites.

Cases of wine in a cellar

You will also have the opportunity to discover some of the secrets behind the production of wine in Tuscany! Particular attention will be given to Chianti Classico, Vino Nobile of Montepulciano, and Brunello of Montalcino and their history going back to Medieval times. All wine-related activities will be tailored to the interests and wine knowledge of the group.

The Villa

This 14th century villa overlooking the Siena countryside is nestled in the heart of a 150-acre property surrounded by an organic garden, vineyard, olive grove, two lakes, and sprawling woods. The structure is completely renovated and equipped with state of the art silent, central AC and high-speed internet, both powered by an on-site solar energy system. Though equipped with modern amenities, this villa remains a beautiful reflection of the heritage and aesthetic of this exceptional part of Italy.

A villa in the countryside of Tuscany


  • Discover the beautiful landscapes of Val d’Orcia, as you taste the wines of Brunello of Montalcino, Chianti Classico, and Vino Nobile of Montepulciano.
  • Visit the estate of one of the original five families of Brunello, taste their wine, and learn about their history. You will be treated like one of the family!
  • Visit the Guicciardini Family farm, winery, and family estate in Chianti, which includes a charming chapel with 16th century frescoes.
  • Learn about the wine culture from local industry experts and walk through the wine production facilities of some of the region’s most exclusive wineries with private tours guided by the owners themselves!
  • Explore picturesque villages and towns like San Gimignano and Siena as you immerse yourself in a uniquely Tuscan experience. 
  • Discover a 14th century castle with splendid views and a priceless art collection that is open only to villa guests.
  • Enjoy a private wine tasting at the villa with a professional sommelier.
  • Learn about the local culinary tradition and taste how certain dishes are best paired with particular wines. 
  • Learn how to cook an authentic, organic, Italian meal, and enjoy it afterwards! 
  • Visit the local open markets, where you will be able to practice your Italian language skills and buy all the ingredients to realize your dishes.
  • Relax by the pool immersed in the beauty of Val d’Orcia as you sip the estate wine grown and processed by the Guicciardini family themselves. 


The package includes:

  • Accommodations in Florence and at an exclusive villa near Siena.
  • All breakfasts, lunches, and most dinners. 
  • Italian language and culture classes at Middlebury Language School in Florence.
  • Transportation to and from all excursions and to and from the villa and *hotel. 
  • Customized cultural excursions in Florence and in Val d’Orcia.
  • Wine tastings with sommelier and wine producers.
  • Entry fees for all excursion to wineries and cultural sites.
  • Italian cooking classes at the villa.

Accommodations: In Florence, you will stay in a very well-situated and comfortable 4-star downtown hotel at walking distance to many of the highlights. In the countryside, you will stay at a 14th century villa, which includes beautifully renovated rooms with exceptional views from each. At the Villa, all rooms have their own bathroom with modern amenities and a semi-private living area suite that is shared with one other room (some suites have independent kitchens as well). In addition to the bedroom suites, there is also a common living room, kitchen, dining room, and a pool area.

Excursions: These are very unique experiences organized in collaboration with local wine industry experts and well-established cultural consultants from the Tuscany region. While our guests will have plenty of opportunities to explore and learn through these high-touch experiences, we are mindful of their need to relax and absorb the local culture and the space on their own time. For this reason, we have included some down time at the villa and on several of the evenings in Florence, so our guests can relax and explore at their own pace.

Transportation: *Airfare and transportation from the airport to the hotel are not included, but all other transportation associated with our organized activities is included. For the departure day, we have two vans and can take a group from the villa to the airport in Florence at two different times (we will try to accommodate the group’s needs).

Detailed Program Cost: All guests will receive the same level of attention and engage in the same experiences throughout the program. Each of the six rooms at the villa are beautiful and unique with an amazing view of the hills of Tuscany. All have private bathrooms and access to semi-private living room suites. However, as this is an authentic Tuscan home, some of the rooms are larger than others, so there are three pricing options.

  • Luxury Option: $6,700/person - Double Occupancy Only
  • Deluxe Option: Double Occupancy $6,400/person; Single Occupancy $6,900
  • Standard Option: Double Occupancy $6,100/person; Single Occupancy $6,700 

*Airfare not included

Our partners

Custom Language Services at the Middlebury Institute of International Studies

Custom Language Services (CLS) offers language and cross-cultural training, program development, and curriculum design customized specifically to meet the language and intercultural training needs of the individual or groups involved. It focuses on applying practical skills through the use of authentic materials and real-world interactions.

Middlebury School in Italy

Since 1915, Middlebury Language Schools has been one of the nation’s preeminent language learning programs. Middlebury Schools Abroad offers programs in 17 different countries. The Middlebury School in Italy is situated in downtown Florence at Sede Capponi. Here it will be possible to accommodate both beginning learners and more proficient ones.

University of Florence

The modern university dates from 1859, and the Faculty of Oenology and Viticulture is within the School of Agriculture, one of the 12 of the University.

The Guicciardini and Biagini Families of Florence

The owners of the villa and family-run winery Fattoria Majnoni Guicciardini will be your hosts at the villa and are also co-organizers of the excursions throughout the Siena region.