Explore the enchanting region of Chianti and bask in the timeless charm of San Gimignano, a hilltop gem best experienced in the golden light of late afternoon after the crowds have dissipated. Begin your journey with a drive through the Chianti countryside, a landscape adorned with towering cypress trees, sprawling oak woodlands, and carefully manicured vineyards. Visit a prestigious Chianti wine estate, where you’ll delve into the art of winemaking with a guided tour of the cellars followed by a flavorful tasting session of Chianti Classico wine and fragrant olive oil. Continue your journey to the ancient fortress town of Monteriggioni, a perfectly preserved medieval stronghold encircled by walls and towers. Dating back to the 13th century and immortalized in Dante’s Divine Comedy, Monteriggioni once stood as Siena’s primary defense against Florence and now remains a serene village full of historic charm. Arrive in San Gimignano in the late afternoon, when its medieval towers glow in the soft sunlight. Enjoy leisure time to explore attractions such as the Civic Museum and the Cathedral, shop for artisanal leather goods and hand-painted ceramics, or savor local specialties in gourmet food shops and inviting wine bars. As the day winds down, head to a local organic farm for a full-course Tuscan dinner. Delight in Vernaccia white wines and robust Chianti reds while dining alfresco on a terrace overlooking the fields and San Gimignano’s iconic skyline, or in a warm indoor setting if the weather calls for it.

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