Flavors of Chianti

Flavors of Chianti

Embrace the bewitching enchantment, bucolic ambiance, and charismatic culture of Chianti.

Meander through Tuscany’s colorful cities, cypress-studded hilltop towns, classic cucinas, and idyllic vineyards during this small-group journey. Explore this Italian countryside that provides overwhelming inspiration for artists, chefs, and vintners alike.

Each invigorating day is enriched by historical site visits, cultural activities and interactions, memorable cuisine, and festive wine tastings.

With your small group, enjoy seven nights deluxe accommodations in the luxurious hilltop Castello La Leccia in Castellina featuring exceptional views of the lush, rolling Tuscan landscape. Visit the childhood home of Lisa Gherardini—immortalized as the Mona Lisa by Leonardo da Vinci—at villa Vignamaggio. And work side-by-side with Italian chefs during a cooking class and wine tasting in Greve.

Enjoy a stroll through spectacular Siena—a UNESCO World Heritage Site—with its well-preserved cityscape, celebrated Duomo, and bustling Piazza del Campo. Admire the Etruscan ruins and Roman center at Volterra before visiting charming San Gimignano—the Town of Fine Towers—which is completely encircled by medieval walls.

At Podere Il Casale—an organic farm—learn about the owners’ passion for the slow food movement and see a cheese-making demonstration. And learn the history of Bagno Vignoni, a small village surrounded by thermal waters.

Trip Itinerary:

September 30 En Route from U.S.

October 1 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)

October 2 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 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)

October 3 Pienza

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)

October 4 Greve

Today, venture down the historic highway known as the “Chiantigiana” to visit La Fattoria di Vignamaggio—halfway between Greve and Panzano in Chianti. This farmstead is a magical place, amidst vegetable gardens and orchards, which provide fresh ingredients for the kitchen. Explore the Laboratori dell’Attesa (the ageing rooms), where different production methods of vinegar, Vinsanto, and extra virgin olive oil will be demonstrated.

Afterward, delight in the panoramic views over the Chianti hills during a wine tasting and food pairing.
Overnight: Castello La Leccia (B,L,D)

October 5 Cortona

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)

October 6 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 are well-preserved today. Enjoy extra time unwinding in a courtyard, visit the small shops, or venture 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 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)

October 7 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 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)

October 8 Castellina / 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 transfer to Florence by private bus. (B)

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