Sunset Wine Tour to Chianti and San Gimignano from Siena

Meet your guide at 2:30 PM under the large tree in Piazza San Domenico, Siena, to embark on a journey through the enchanting Chianti countryside. Begin with a visit to a Chianti wine estate, where you’ll tour the vineyards and wine cellars, learning about the winemaking process before indulging in a tasting of their celebrated wines.

Next, discover Monteriggioni, a perfectly preserved medieval fortress encircled by 13th-century walls and turrets, famously mentioned by Dante in the Divine Comedy. Stroll its cobbled streets and imagine life in the Middle Ages.

Continue to the UNESCO World Heritage site of San Gimignano, known as the "Town of Towers." Arriving as the daytime crowds dissipate, you’ll have time to explore its romantic medieval streets, marvel at its architecture, visit boutique shops offering local crafts and saffron, or sample Vernaccia di San Gimignano wine. For panoramic views, take a short walk to the Rocca fortress overlooking the iconic towers and rolling hills.

Conclude your day with a visit to a family-run farm, where a delightful Tuscan dinner awaits, complete with the farm's own wines. Weather permitting, enjoy your meal outdoors under the Tuscan sky (don’t forget a jacket for cooler evenings).

The wine tasting typically includes three or four wines and sometimes features a sampling of extra virgin olive oil. For the dinner at the estate, guests are served a four-course meal accompanied by three wines, or four when Vinsanto, a dessert wine, is paired with the final sweet course.