Tuscany Sunset Tour & Dinner, Siena

Visit the hills of Chianti and take in the magic of San Gimignano, best appreciated when the tourists leave and the romantic afternoon light takes hold. In the evening, enjoy a traditional dinner at a local farm overlooking the towers and the soft rolling, vine-covered hills.

Start with a scenic drive through the Chianti region. You’ll pass dense oak forests, cypress trees, neat rows of vineyards, and landscapes shaped into works of art. You’ll first visit a Chianti wine estate and its wine cellars, learning about the winemaking process. Afterward, enjoy a tasting of Chianti Classico wine and olive oil. You’ll then make your way to Monteriggioni, a medieval and perfectly preserved fortress with a complete ring of walls and turrets. Established in the 13th century, Dante mentioned the castle in his Divine Comedy. Monteriggioni was Siena’s main bastion of defense against the armies of Florence, and today it sits as a quiet and charming hamlet.

In the late afternoon, you’ll arrive in San Gimignano when the crowds of the day have left. Enjoy some free time to roam this beautiful and romantic “town of towers” at a leisurely pace. There’s plenty to do in the hilltop village, such as visiting the Cathedral or Civic Museum, shopping in the many artisanal boutiques selling leather and hand-painted pottery, and sampling local products in the food stores and wine bars.

After San Gimignano, you’ll head out of town to an organic farm and enjoy a full Tuscan dinner. Pair your meal with wine tastings of famous whites from San Gimignano, Vernaccia, and red Chianti. Weather permitting, you’ll enjoy dinner on a terrace overlooking the cultivated fields and San Gimignano during sunset. During colder months or bad weather, you’ll savor your meal inside a cozy dining room. 

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