Day 1: En Route from U.S.
Thursday, June 5, 2025

Day 2: Arrive in Florence, Italy | Castellina
Friday, June 6, 2025
Upon arrival to Florence’s Peretola Airport an Orbridge representative will be waiting to assist with your transfer to the property.

Dating back to the Middle Ages, Castello La Leccia exudes an aura of history—its architecture a testament to the castle’s rich past. Stone walls, turrets and charming courtyards seemingly transport you to a bygone era. Stepping into your accommodations, you’ll appreciate the blend of classic opulence and contemporary elegance. Comfortable furnishings, plush bedding and stunning views create a quaint haven in which to retreat after enriching days of exploration.

Take time to unpack and settle in before joining fellow travel companions for a convivial four-course welcome dinner.
Overnight: Castello La Leccia (D)

Day 3: Castello La Leccia
Saturday, June 7, 2025
Today meet with chefs from the property for an informative, hands-on cooking experience. Learn the secrets of preparing traditional pasta and bread, then indulge on your creations during a leisurely lunch.

The remainder of the afternoon, take advantage of free time to fully immerse yourself in Castello La Leccia’s varied amenities. Stroll through the meticulously maintained gardens where the fragrance of lavender and rosemary fills the air. Admire the endless panoramic views as you relax by the outdoor pool. Or opt for a rejuvenating treatment (additional fees apply) at the tranquil spa.

Later gather together for a guided tour to explore the vineyards and production area. Learn about the winemaking process, and savor the varietals during a tasting.
Overnight: Castello La Leccia (B,L,D)

Day 4: Pienza
Sunday, June 8, 2025
Following breakfast set out for the charming village of Pienza. Known as “the ideal city of the Renaissance,” this UNESCO World Heritage Site 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 for centuries.

Continue to Podere Il Casale, a small organic farm, to 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. Join them on a tour of the vineyard, olive groves, animal sanctuary and cheesemaking workshop, and gain insight into the concept of the slow food movement. This integrated approach unites the enjoyment of growing, preparing and eating food in harmony with nature. After walking the grounds, be seated for lunch featuring ingredients grown on and harvested from the farm.

Return to the property with time to freshen up before another five-star gastronomic experience—a specially crafted four-course dinner carefully paired with wines from the region.
Overnight: Castello La Leccia (B,L,D)

Day 5: Cortona
Monday, June 9, 2025
After breakfast travel to the hilltop town of Cortona—the adopted home of Under the Tuscan Sun author, Frances Mayes.

A local guide will escort you through neo-Gothic Santa Margherita Basilica, past Villa Bramasole, around Cortona’s city center, and to the Etruscan museum.

The remainder of the afternoon is at leisure. Stop for lunch at one of Cortona’s many charming cafés or restaurants, then meander the winding streets exploring the various shops and boutiques.
Overnight: Castello La Leccia (B,D)

Day 6: Volterra | San Gimignano
Tuesday, June 10, 2025
Today marvel at the ancient allure of 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 carve unique handmade alabaster crafts and souvenirs. Stroll through the bustling, narrow streets before reaching an overlook to view the ancient Roman theatre. Glimpse clouds of geyser steam in the distance as it escapes over the rolling hillside.

Continue to San Gimignano—the “New York of the Middle Ages” and UNESCO World Heritage Site—whose horizon of iconic towers resembles modern skyscrapers. During an inside visit of San Gimignano’s Romanesque Duomo, view colorful frescoes including The Creation of Adam and Eve and Last Judgement. Learn the story of local Saint Fina, 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, June 11, 2025
Following breakfast 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. See the medieval abbey at Abbadia a Isola, then stroll through the shops in the small village of Castellina in Chianti.

This evening features an exclusive culinary adventure—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 radiates spirited fun in the kitchen while she demonstrates the simple techniques and preparations of classic Tuscan dishes.

The property itself exudes an enigmatic atmosphere—melding centuries-old history with family traditions passed down through generations. During a tour of the Renaissance garden and cellar system, hear 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 developing a flourishing wine business. Since 1846 the winery continues under private ownership of the Stucchi Prinetti family.

Afterward gather together in the dining room for a special dinner.
Overnight: Castello La Leccia (B,L,D)

Day 8: Siena
Thursday, June 12, 2025
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 join fellow travel companions for a farewell dinner at Castello La Leccia, and celebrate the captivating week spent exploring Tuscany.
Overnight: Castello La Leccia (B,D)

Day 9: Castellina | Florence | Depart for U.S.
Friday, June 13, 2025
After breakfast guests departing during the suggested times take a complimentary group transfer to the airport for flights home.

Guests continuing on the post-tour will transfer to Florence by private bus. (B)

B = Breakfast, L = Lunch, D = Dinner