Late summer in Italy can resemble a special circle of Dante’s Inferno—one filled with too many tourists in tar-melting heat as Italians flee their work posts to go to the beach or mountains. But then, occasionally, even in summer, Italians do what they do best: surprise you with rabbit-out-of-the-hat magic that leaves you agape.

That charming wizardry was in full force in coastal Tuscany, at the Bolgheri appellation’s 30th anniversary “Dinner for a Thousand,” staged Sept. 4 along the iconic, cypress-lined road that passes under Bolgheri’s medieval castle.