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 the Italian countryside that provides endless inspiration for artists, chefs, and vintners alike.
Day 1: En Route from U.S.
Day 2: Arrive in Florence, Italy / Castellina
Day 3: Volterra / San Gimignano
Day 4: Pienza
Day 5: Greve
Day 6: Cortona
Day 7: Monteriggioni / Via Francigena / Gaiole
Day 8: Siena
Day 9: Florence / Depart for U.S.
• With your small group (maximum 22 guests), enjoy seven nights deluxe accommodations at the luxurious and exclusive Castello La Leccia in Castellina, featuring exceptional views of the lush, rolling Tuscan landscape.
• Admire the Etruscan ruins and Roman center in Volterra before visiting charming San Gimignano—the Town of Fine Towers—which is completely encircled by medieval walls.
• Stop at the Renaissance town of Pienza, a UNESCO World Heritage Site, which sits atop a hill overlooking the Tuscan countryside.
• Discover Podere Il Casale, an organic farm. Tour the grounds while learning about the owners’ passion for the slow food movement, followed by a leisurely lunch.
• Visit La Fattoria di Vignamaggio to explore the grounds and ageing room before a wine tasting and food pairing.
• Take a guided tour of Cortona with free time to explore afterward.
• Wander within the walled medieval village of Monteriggioni—a city along the ancient pilgrim road of Via Francigena—before strolling down the road to visit the Abbadia a Isola abbey.
• Savor a cooking class and dinner at Badia a Coltibuono, a remarkable winery featured on the Netflix TV show, Salt Fat Acid Heat.
• Stroll Siena—another UNESCO World Heritage Site—with its well-preserved cityscape, celebrated Duomo, and bustling Piazza del Campo.
What’s included: 7 nights accommodations; 7 breakfasts, 3 lunches, and 7 dinners served with wine; all lessons and tastings as described in the 9-day itinerary; private motor coach transportation; luggage handling; gratuities to Orbridge Travel Director, local guides, drivers, porters, and wait staff for included meals; and group airport transfers for guests arriving and departing during the suggested times.