Hit the open road in true Italian style as you cruise through the gorgeous Tuscan countryside from behind the wheel of a vintage Fiat 500. Starting in the rolling hills of Monteriggioni, wind along roads bordered by vineyards and olive groves before stopping at a local winery.

Enjoy the independence of driving your very own classic Fiat and follow your tour guide—who leads the convoy of little cars. Open up the sunroof and feel the wind in your hair as you speed along in your classic icon of Italian car manufacturing. The cars are very simple, and—more importantly—a lot of fun to drive. You also have the option to travel as a passenger if you prefer not to drive yourself.

Pass through the Chianti wine region and stop at a hand-picked local winery for a wine tasting with samples of some homegrown Chianti wine before hopping back in your car and making your way back to Siena.