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.

Program Itinerary:

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.