Orbridge: (866) 639-0079 or Email
+Itinerary

Flavors of Chianti

Day 1: En Route from U.S.
Day 2: Arrive in Florence, Italy / Castellina
Day 3: Volterra / San Gimignano
Day 4: Pienza / Bagno Vignoni
Day 5: Greve
Day 6: Cortona
Day 7: Monteriggioni / Via Francigena / Gaiole
Day 8: Siena
Day 9: Florence / Depart for U.S.

Optional Post-Tour: Florence

Day 1: En Route from U.S.

Day 2: Arrive in Florence, Italy / Castellina
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: Volterra / San Gimignano
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 on 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 some of 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 4: Pienza / Bagno Vignoni
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 on 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, and sharing the concept of the slow food movement, which emphasizes an integrated approach uniting the enjoyment of growing, preparing, and eating food in harmony with nature, with others.

After touring the grounds, enjoy a delectable lunch created from ingredients grown on and harvested from the farm.

Before returning to Castello La Leccia, stop at Bagno Vignoni, a small medieval village from the Roman times situated around a scenic piazza of thermal waters. Learn the story of St. Catherine of Siena, one of Italy’s patron saints, and how this village was instrumental to achieve her calling.
Overnight: Castello La Leccia (B,L,D)

Day 5: Greve
Today, venture to Villa Vignamaggio, the childhood home of Lisa Gherardini—who was later immortalized as the Mona Lisa in the iconic artwork painted 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.

Partake in a lively cooking class to learn the secrets of traditional Tuscan cuisine. Back on the garden terrace, a leisurely white linen al fresco lunch and wine tasting await.

Later this afternoon, enjoy a bit of free time to wander the area's unique shops or perhaps sip a macchiato at an outdoor cafe.
Overnight: Castello La Leccia (B,L,D)

Day 6: Cortona
After breakfast, travel to the hilltop town of Cortona—the adopted home of Frances Mayes who wrote Under the Tuscan Sun. Set out on a guided tour including a visit to Le Celle, a 13th-century Franciscan convent that was briefly the home of St. Francis of Assisi (who also helped build the first rooms of the structure in 1211). Currently, the hermitage is inhabited by seven friars who continue to practice the preachings of St. Francis.

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 7: Monteriggioni / Via Francigena / Gaiole
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 remain incredibly preserved today. Enjoy extra time unwinding in a courtyard, visiting the small shops, or venturing along Via Francigena down to Abbadia a Isola, a medieval abbey.

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 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 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.
Overnight: Castello La Leccia (B,L,D)

Day 8: Siena
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 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: Florence / Depart for U.S.
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 remain in Florence. (B)

B=Breakfast, L=Lunch, D=Dinner
(Itinerary subject to change.)

Activity Level:

Moderate

Activities are generally not very strenuous, however, this program requires individuals to 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.