Skip to main content
Lush vineyards on the hilly Chianti countryside
View from the rooftops overlooking Siena
Cortona town hall
Stautue of a man holding grapes outside Villa Vignamaggio
Villa Vignamaggio gardens
Villa Vignamaggio arched walkway through gardens
Panoramic cityscape of Siena
Panorama of medieval Siena with dome of Siena Cathedral and Mangia Tower
Siena Cathedral in Siena
Piazza del Campo of Siena
Piazza del Campo at the interior of Siena
Rooftop view overlooking Volterra
Ancient Roman ruins in Volterra
Etruscan ruins
Panoramic cityscape of the medieval town of San Gimignano
Piazza della Cisterna in the historic town of San Gimignano on a sunny day
Fortification at San Gimignano
Stone towers inside San Gimignano
Bird's-eye view over Monteriggioni
Stone pathway surrounding fortification
Rainy street in Monteriggioni
Quiet side street in Monteriggioni
Medieval fountain and buildings in Monteriggioni
Wide panorama of Monteriggioni
Wide panorama of Pienza
Charming colorful side street in Pienza
Pienza cathedral
Podere Il Casale, a small organic farm in Pienza
Sheep walking along path
Sheep grazing at Podere Il Casale
Al fresco dining area
Dessert-making class
Ingredients for cooking class
Scenic outdoor dining
Cheese platters at Podere Il Casale
Lush green landscape of Chianti's rolling hills
Flavors of Chianti

Flavors of ChiantiItinerary

September 7 – September 15, 2023

Day 1: En Route from U.S.
Thursday, September 7, 2023

Day 2: Arrive in Florence, Italy / Castellina
Friday, September 8, 2023
Welcome to lovely Italy! After arriving at the property, unpack and relax before joining fellow travel companions for a welcome dinner. If time allows, meander Castello La Leccia's tranquil garden and courtyard with panoramic views of Tuscany's seemingly endless countryside.
Overnight: Castello La Leccia (D)

Day 3: Castello La Leccia
Saturday, September 9, 2023
Revel in la dolce vita by spending today at the wonderful Castello La Leccia accommodations and enjoy a cooking class, lunch, winery tour/tasting, and dinner. 

Here at home base, we'll learn secrets of traditional Tuscan food with an informative and fun cooking class. Experience the preparation of Italian homemade pasta and bread with chefs and then savor the fruits of the labor by dining on a sumptuous lunch. 

The afternoon is open for leisure at this wonderful property. Hike the trail surrounding the castle to take in the views, stroll the gardens, unwind by the pool, or purchase a yoga or Shiatsu class or a spa treatment (additional fees apply).

Later, delight in the panoramic views over the Chianti hills during a behind-the-scenes winery tour and tasting. 
Overnight: Castello La Leccia (B,L,D)

Day 4: Pienza
Sunday, September 10, 2023
The charming village of Pienza awaits. Known as "the ideal city of the Renaissance," this UNESCO World Heritage Site, perched on a hill in Southern Tuscany, was designed to exemplify the principles and philosophy of classical times and the great Italian Renaissance. Constructed within approximately four years, the village has remained unchanged over the centuries. 

Continue to 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. Gain insight into the concept of the slow food movement, which emphasizes an integrated approach that unites the enjoyment of growing, preparing, and eating food in harmony with nature.

After touring the grounds, enjoy a delectable lunch created from ingredients grown on and harvested from the farm.  
Overnight: Castello La Leccia (B,L,D)

Day 5: Cortona
Monday, September 11, 2023
After breakfast, travel to the hilltop town of Cortona—the adopted home of Frances Mayes, author of Under the Tuscan Sun. Enjoy a guided tour to visit the church of Santa Margherita, the panorama, Bramasole villa, the city centre of Cortona, and the Etruscan museum.

The afternoon is at leisure in Cortona's town center. Stop at one of the many charming eateries for lunch on your own, and explore the various small shops lining the bustling streets.
Overnight: Castello La Leccia (B,D)

Day 6: Volterra / San Gimignano
Tuesday, September 12, 2023
Enjoy a traditional Italian breakfast before setting out for 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. Leisurely stroll through the narrow streets before reaching an overlook to view the ancient Roman theatre. Off in the distance, glimpse clouds of geyser steam as it escapes over the rolling hillside. 

Continue to the "New York of the Middle Ages" and UNESCO World Heritage Site, San Gimignano—whose skyline from a distance resembles a modern city. During an inside visit of San Gimignano’s Romanesque Duomo, behold colorful frescoes, including The Creation of Adam and Eve and Last Judgement. Also, 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.

After lunch on your own, rejoin fellow travel companions in the main square for a special treat—a visit with Sergio Dondoli, master gelato creator and owner of Gelateria Dondoli—winner of numerous awards and recognitions. Sergio's boundless passion for his craft is contagious as he boisterously describes his most popular flavors, including Rosemary Baby, Cream of Santa Fina, and Zabaione di Vinsanto. Afterward, visit the gelateria for a sampling of his decadent creations.Overnight: Castello La Leccia (B,D)

Day 7: Monteriggioni / Castellina in Chianti / Gaiole
Wednesday, September 13, 2023
Today, visit the walled medieval village of Monteriggioni—a popular stop on the Via Francigena pilgrim trail, an ancient route that connected Canterbury to Rome in medieval times. Built between 1213 and 1219, the castle's fortified walls and 14 guard towers are well-preserved today. Visit Abbadia a Isola to see the medieval abbey and then stroll around the small shops in the charming hilltop village of Castellina in Chianti.

This evening features 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, as well as the author of several cookbooks. Benedetta exudes spirited fun in the kitchen while teaching the simple techniques and preparations of classic Tuscan dishes. 

During the visit, learn of the winery's history dating back to the 11th century when it was founded by monks of the Vallumbrosan 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 that 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 through generations. Tour the Renaissance garden and noteworthy cellars followed by a special dinner.
Overnight: Castello La Leccia (B,L,D)

Day 8: Siena
Thursday, September 14, 2023
Today'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 remain unchanged. Explore the celebrated Duomo, with its striking striped columns and walls, and recently excavated 13th-century frescoes. Admire the Sanctuary of Santa Caterina—a place of pilgrimage—and learn about the city’s colorful history.

During free time, wander the shell-shaped Piazza del Campo—one of Europe’s finest squares—built on the site of a Roman marketplace. 

This afternoon, meet Lorenzo Rossi, a third-generation artisan baker and owner of Il Magnifico. Lorenzo will share his special family traditions and the ingredients unique to his creations during a tasting of fresh-baked Sienese sweets.

Tonight, share your experiences from a captivating week spent in Tuscany and raise a glass with fellow travel companions one final time at Castello La Leccia during a convivial farewell dinner.
Overnight: Castello La Leccia (B,D)

Day 9: Castellina / Florence / Depart for U.S.
Friday, September 15, 2023
After breakfast, guests departing during the suggested times take a complimentary group transfer to Florence's Peretola Airport for flights home. Guests continuing on the post-tour will transfer to Florence by private bus. (B)

B = Breakfast, L = Lunch, D = Dinner

(Itinerary subject to change.)

Activity Level:


Activities are generally not very strenuous, however, this program requires individuals have higher mobility due to many steep hills, streets, and stairs in each town visited. We expect that guests can enjoy two hours or more of walking, are sure-footed on cobbled surfaces, and can walk up and down stairs without assistance. Historic city centers are usually more accessible by foot than vehicle, and often it is not possible for your motor coach to drop you off at site entrances. Due to the structure of some buildings, facilities for persons with disabilities may be limited.