Your journey begins as you drive along the cypress-lined driveway, your eyes settling on the majestic Borgo Scopeto Relais. This former noble residence will be your stylish home for the coming days. On the hotel terrace, with a breathtaking view of Siena, you’ll meet your fellow travelers. The sight of the gleaming Mercedes-Benz fleet in the gravel-covered courtyard of Borgo Scopeto gives you chills. The moment you turn the ignition key for the first time and drive out your Mercedes-Benz SL classic, your heart races. You glide effortlessly over the gentle hills of the world-famous cultural landscape of Chianti, with ancient castles and fortresses in view. After this diverse first day of driving, you’ll reflect on the day’s impressions in the refined ambiance of Borgo Scopeto.

The exact route of Italy’s most famous car race is still unknown, but one thing is certain: today, you’ll experience automotive history up close. The legendary “Mille Miglia,” with its several hundred participating classic cars, makes the hills of Tuscany tremble. Your excursion today in “your” Mercedes-Benz SL is planned so that you witness a city passage of the race cars, primarily from the pre-war era, and are close enough to touch the drivers and vehicles. If you’re tempted to join the convoy after the passage and ride along for a bit: go for it! In the evening, we take you to an agriturismo known for its remarkable cuisine and charming atmosphere.

This remarkably impressive stage partially follows ancient pilgrim routes, passing southwest of Siena into the Val d’Orcia. In Pienza, named after Pope Pius II, who transformed his birthplace into a jewel of the Renaissance, a guided tour awaits you. For your lunch break, there are many typical “trattorie” to choose from, some offering spectacular views of the Val d’Orcia. The return journey takes you through a Tuscan postcard landscape, the “Crete Senesi,” where one cypress-lined hill follows another. Along the crest of these steep clay slopes, the country road winds its way. The hotel terrace, with its spectacular view of Siena and the surrounding vineyards, provides the perfect setting for an atmospheric aperitivo in the evening light.

On this day we drive winding country roads and lonely mountain roads via Poggibonsi in the direction of San Gimignano . San Gimignano is world famous for its high number of surviving family towers, which are only stumps in other cities, and for its almost unchanged medieval appearance. During a city tour, we stroll through the historic old town, which was declared a World Heritage Site by UNESCO in 1990, and see the slender towers that characterize the cityscape. This fact has given the place the nickname “Manhattan of the Middle Ages”. After an individual lunch break, we set off for the last stage in the direction of the Citadel of Monteriggioni . There you will say goodbye to “your” Mercedes-Benz SL, we will accompany you back to Florence Airport or to the hotel if you are arriving by car.