Your day begins with a personal pickup by your English-speaking driver from your hotel or apartment in Rome. After a quick introduction, settle into your private ride and set off through the Tuscan countryside towards Siena – a medieval gem renowned for its wines and timeless charm.

Enjoy a relaxing drive past rolling hills, vineyards, and rustic landscapes. Your driver will share local insights along the way, suggesting scenic photo stops at landmarks of interest. As the tour is fully customisable, you can decide where and for how long to stop, tailoring the journey to your pace.

Arriving in Siena, step into the UNESCO-listed Historic Centre and explore Piazza del Campo, the city’s beating heart. This shell-shaped square is a favourite gathering place for locals and visitors alike, home to charming cafés, the striking Fonte Gaia fountain, and the Civic Museum, which houses masterpieces by Sienese artists.

Just above lies Siena’s Duomo, a gothic masterpiece adorned with striking black-and-white marble stripes, the city’s symbolic colours. Inside, the cathedral boasts an extraordinary collection of works by Italy’s greatest artists. Even if you only admire it from the outside, the grandeur of its façade is unforgettable.

From Siena, your driver will whisk you away to San Gimignano, a UNESCO World Heritage Site famed for its medieval towers. Once boasting 72 soaring structures built by wealthy merchant families, the town still preserves 15 of these icons of medieval rivalry. Wander through the Piazza della Cisterna, admire its 13th-century walls, and soak up the atmosphere of this enchanting hilltop town.

No trip to Tuscany would be complete without wine. Along the way, your driver will suggest wineries and wine cellars where you can pause to enjoy tastings. We recommend Brunello di Montalcino, one of Italy’s finest wines, best enjoyed with local cheeses and cured meats for a perfect light lunch.

After a day of history, architecture, and indulgent flavours, relax on the return drive through Tuscany as your driver brings you back to your accommodation in Rome.