Embrace the bucolic ambiance and charismatic culture of Chianti’s colorful cities, cypress-studded hilltop towns, classic cucinas, and idyllic vineyards.


  • Enjoy seven nights in an elegantly appointed property on a hilltop in Castellina, featuring exceptional views of the lush, rolling Tuscan landscape.
  • Admire the Etruscan ruins and Roman center at Volterra before visiting charming San Gimignano, which is completely encircled by medieval walls.
  • At Podere Il Casale–an organic farm–learn about the owners’ passion for the slow food movement, watch a cheese-making demonstration, and savor a leisurely, locally sourced lunch.
  • Visit Villa Vignamaggio, the childhood home of Lisa Gherardini, who was immortalized in the Mona Lisa by Leonardo da Vinci.
  • Stroll through Siena—a UNESCO World Heritage Site—with its well-preserved cityscape, celebrated Duomo, and bustling Piazza del Campo.

Itinerary at a Glance

May 14Depart gateway city
May 15Arrive in Florence, Italy | Castellina
May 16Volterra | San Gimignano
May 17Pienza | Bagno Vignoni
May 18Greve
May 19Cortona
May 20Monteriggioni | Gaiole
May 21Siena
May 22Florence | Depart for U.S.

Optional Extension(s)

Post-tour: Florence