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A Tuscan Adventure with Il Chiostro!

The Tuscan countryside photo by Janine Queenin
Story and photos by Janine Queenin

When I dreamed of Tuscany, I imagined lush, green rolling hills, picturesque vineyards, and medieval villages with 1,000-year-old walls and secret alleys that lead to breathtaking views across the countryside. Now that I’ve seen it firsthand, I realize my imagination wasn’t even close.

Each fall, Il Chiostro runs workshops throughout Italy, culminating with the Autumn Arts Festival at Dievole Wine Resort in Vagliagli near Siena. This year, I was lucky enough to attend as one of the hosts for the Sights, Aromas, and Tastes of Tuscany workshop; the experience was enchanting.

The workshops run at several venues in Tuscany, all of which are unique and an essential part of the experience for guests. From the moment I arrived at Dievole, I knew it was special. For over 1,000 years, wine and olive oil have been lovingly produced here under the Tuscan sky. That means the landscape is stunning, and the resort is bordered by vineyards grown to produce Dievole’s wines.

The property is sprawling, with buildings linked by cobblestoned pathways and beautifully landscaped spots to relax and enjoy a cappuccino or glass of wine while taking in the view. The resort’s centerpiece is the 18th-century manor house with elegant rooms designed for comfort and style. While I could have spent all of my time at Dievole, there were too many things to see and do to stay in one place.

Autumn is a great time to visit Italy, the crowds are smaller, and things seem to unfold at more relaxed pace. The colors are vivid; reds, oranges, and gold fill the fields and hills beyond. The shorter days are warm and encourage lingering in the sunshine. There is a special magic in Tuscany in autumn that must have something to do with the harvest and the wonderful fresh food and wine available at that time of year.

Il Chiostro guests eating al fresco in Tuscany - photo by Janine Queenin

And, boy, did we enjoy the food and wine. First was the fantastic food at Dievole. The meals were a special highlight for me, starting with a fresh, beautifully prepared breakfast buffet and ending with a sumptuous dinner created for our group and paired with wine from the resort. We also traveled into the countryside to visit Siena, Pienza, and San Gimignano to explore and visit the oldest bakery in Siena, and sample local cheese, cured meats, balsamic, and handcrafted gelato. We also received a lesson in olive oil, and now I’ll never buy a generic supermarket gallon of olive oil again.

One highlight was cooking, eating, and drinking with Chef Andrea Anichini. Our group spent the day at his house overlooking his family’s vineyard and created a delicious meal with only the freshest local ingredients (some from his yard) and wine lovely crafted by his cousin at the winery next door. 

While the Tuscan countryside, Dievole, and the food certainly played a starring role in my adventure, the people I met made it magical. Il Chiostro often hosts more than one workshop at a location. While my group ate and drank wine around the countryside, others painted, created collages, learned about opera, and fine-tuned their skills with a camera. Il Chiostro offers more than 60 creative workshops for all skill levels during the spring and fall, and you’re sure to find something to spark your creativity. 

Linda and Michael like to say that once you participate in an Il Chiostro workshop, you are part of the Il Chiostro family for life. By the end of our week, hugs were shared, and tears of joy were shed over new friendships and a connection that would last a lifetime.

So what makes the Il Chiostro experience so special? Simple, experience, expertise, a love of Italy, and a passion for creating connections between their guest and the country they love.

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