Your Tuscany driving experience begins at Borgo Scopeto Relais, a historic estate surrounded by vineyards and overlooking Siena. After meeting your fellow travelers, you are introduced to the fleet of classic Mercedes-Benz SL models waiting in the courtyard. The first drive leads through the rolling hills of Chianti, past cypress-lined roads, castles, olive groves, and medieval villages. In the evening, relax over dinner and wine in the refined atmosphere of the estate.

Today you experience the Mille Miglia firsthand. Known as “La Corsa Più Bella del Mondo,” the Mille Miglia remains one of the most celebrated historic car events in the world. Driving your Mercedes-Benz SL through the Tuscan countryside, you position yourself along the route to witness hundreds of legendary pre-war and post-war classic cars passing through historic towns and villages. The atmosphere is unforgettable, combining motorsport history, Italian passion, and the beauty of Tuscany.

Today’s route follows some of Tuscany’s most iconic roads. South of Siena, your classic Mercedes-Benz glides through the Val d’Orcia, a UNESCO-listed landscape of vineyards, cypress trees, and hilltop villages. In Pienza, the ideal Renaissance town created by Pope Pius II, you’ll have time to explore historic streets and enjoy lunch overlooking the countryside. The return drive through the Crete Senesi delivers the postcard Tuscany many travelers imagine: winding roads, golden hills, and endless panoramic views.

The final driving stage takes you through quiet country roads toward San Gimignano, famous for its medieval towers and remarkably preserved historic center. Often called the “Manhattan of the Middle Ages,” the town remains one of Tuscany’s most impressive destinations. After time to explore and enjoy lunch, the journey continues toward Monteriggioni, where you return your Mercedes-Benz SL and transfer back to Florence Airport or your hotel.