11 Best Wine Tours and Wineries Near Siena, Tuscany (Chianti & Tuscan Vineyards)

The area around Siena produces some of the region’s most celebrated Chianti Classico wines, built on the Sangiovese grape, with a tradition that goes back centuries.
Many of the best wineries are just a short drive—or even a walk—from the city, making it easy to spend a day tasting, learning, and enjoying the landscape.

March 15, 2026

Hi, we’re Gary and Sally 

“Our European ski story began in the 1980s and has continued with annual trips for the past 25 years. With deep experience across countless alpine resorts, skiing has become more than a sport—it’s our passion and a life that inspires our travels, adventures, and the stories we love to share.”