Flavors of Chianti Enjoy seven days exploring Italy like a local—from dark, earthy cellars brimming with varietals like Chianti Classico, Super Tuscan, and Vin Santo, to aromatic kitchens overflowing with pasta, parmesan, and prosciutto.

Amidst rolling hills, verdant fields, and endless rows of colorful vines abundant with fruit ready for harvest...

Castello La Leccia

...settle into a private villa perched serenely within the lush landscape providing 360-degree views of the pastoral countryside.

Castello La Leccia's historic ancient rock walls, terra cotta tile roof, inviting rooms and common spaces—both indoors and out—and affable staff provide the perfect introduction for an enriching and lively week in Tuscany.

Dine al fresco when weather permits, stroll the tranquil grounds, sit poolside or take a dip, and tour the winery and cellar with your gracious host.

Castello La Leccia's courtyard, pool, and cellar

Your Itinerary

Visit Volterra—an Etruscan and Roman center high atop a hill in a volcanic region—surrounded by fortification walls. Famous for its alabaster quarries, the town's artisans produce unique handmade alabaster crafts and souvenirs.

At San Gimignano, step inside the Romanesque duomo to view the colorful frescoes including The Creation of Adam and Eve, and Last Judgement. Plus learn the story of local Saint Fina while stepping through a dedicated chapel, added in 1468, where the Florentine master Domenico Ghirlandaio depicted her dramatic life.

Volterra's Roman theatre, alabaster workshop, and San Gimignano's cathedral frescoes

Set out for the charming village of Pienza before a remarkable afternoon at Podere Il Casale—a small organic farm—for a behind-the-scenes look at their scenic vineyard, olive groves, animal sanctuary, and cheesemaking workshop. Meet the owners—Ulisse and Sandra—a husband and wife duo who moved from Switzerland to Tuscany in 1991 to pursue their dreams of creating a sustainable farm-to-table lifestyle.

— the countryside surrounding Podere Il Casale —

— a bustling animal sanctuary on the grounds —

— learn about the farm's cheesemaking process —

— appreciate the farm-to-table ingredients that make up a decadent lunch —

Then enjoy a blissful visit to Villa Vignamaggio—the childhood home of Lisa Gherardini—who was later immortalized as the Mona Lisa by Leonardo da Vinci.

Vignamaggio's impressive acreage, which sits serenely amidst lush gardens, stately cypress trees, and whispering streams, cultivates an extraordinary harvest including pomario plants, orchard fruit, olive trees, and endless grapevines. The breathtaking panoramic views from each terrace imprint memories into the soul that will last a lifetime.

Travel to the hilltop town of Cortona for a guided tour including a visit to Le Celle, a 13th-century Franciscan convent that was briefly the home of St. Francis of Assisi.

Le Celle Monastery

The second to last evening offers an exclusive experience—a visit to Badia a Coltibuono winery for a cooking class with Benedetta Vitali, chef and co-founder of Cibreo and Zibibbo restaurants.

Learn of the winery's history dating back to the 11th century when founded by monks of the Vallombrosan Order, a Tuscan reform of the Benedictines. These monks planted the first vineyards in the northern Chianti area. Over centuries, they extended their vast land holdings to include many thousands of acres and developed a flourishing wine business. Since 1846, the winery continues under private ownership of the Stucchi Prinetti family.

The property itself exudes an enigmatic atmosphere—melding centuries-old history with family traditions passed on through generations. Tour the Renaissance garden and noteworthy cellars followed by a special dinner.

Your final day's highlight features a visit to Siena—a UNESCO World Heritage Site—to admire its remarkably well-preserved medieval cityscape. Spared from major modern industrial development and large-scale urban extensions, Siena's original 15th-century street plan and Gothic architecture remains unchanged. Explore the celebrated duomo, with its striking striped columns and walls, ornate mosaic floor panels, and recently excavated 13th-century frescoes. Admire the Sanctuary of Santa Caterina—a place of pilgrimage—and learn about the city’s colorful history.

Siena's cityscape, duomo, city center, and Il Magnifico bakery

Click here learn more about Orbridge's new Flavors of Chianti travel program, or call us at (866) 639-0079.