San Gimignano's fourteen surviving medieval towers—once seventy-two—rise above vineyards that produce Vernaccia di San Gimignano, Tuscany's only white DOCG. The denomination was granted in 1966, revised in 1993, and remains the sole white wine in the region to carry the classification. The town's prosperity, built on saffron trade and the Via Francigena pilgrimage route, ended with the Black Death in 1348; what remained was a frozen tableau of thirteenth-century architecture and an unbroken viticultural tradition on the surrounding hillsides. Today, San Gimignano wine tasting and lunch experiences pair the town's architectural heritage with its agricultural output. Vernaccia vines thrive in the galestro and alberese soils encircling the comune, yielding a mineral-driven white that has been documented since 1276. Chianti Colli Senesi estates occupy the southern slopes, where Sangiovese ripens under the same sun that lights the Duomo's frescoes. A typical san gimignano wine tasting and lunch tour begins in the town's Piazza della Cisterna, then moves into the vineyards where producers offer three to five pours—Vernaccia, Chianti, and occasionally a Vin Santo—paired with hand-rolled pici pasta, pecorino aged in tufa caves, and wild boar ragù. The convergence of viticulture and medieval urbanism defines the experience. Farmhouses converted into agriturismi serve as tasting venues, many within sight of the Torre Grossa, the tallest of the towers at fifty-four meters. Lunch is served outdoors from May through October, under pergolas heavy with sangiovese clusters. The meal structure follows contadino tradition: antipasti of cured meats and preserved vegetables, a primo of pasta or ribollita, a secondo of grilled meat, and a dolce of cantucci dipped in dessert wine. Each course is calibrated to the wine flight, which progresses from the crisp Vernaccia through structured Chianti Riserva to the oxidative sweetness of Vin Santo. The architecture provides context, but the land provides substance. Vineyards planted on terraces built by Etruscan hands yield grapes that become wine served in rooms where frescoes depict the same harvest two centuries prior. The medieval towers, visible from every vineyard, serve as both landmark and reminder that San Gimignano's wealth has always been extracted from the soil—first saffron, now wine.