Montepulciano & Cortona

In Montepulciano, from here we start our pleasant five-mile descent through the vineyards, where the only sound is the wind in our hair. Plunge into some of the most beautiful vineyards in Tuscany. Relaxed and glowing, it's time to set off on a long, slow climb towards Cortona, the delightful hilltown made famous by Frances Mayes in her bestselling novel Under the Tuscan Sun. After lunch at a local trattoria, we'll stroll around Cortona's pristine medieval streets….and then if we're up for it, we'll sail downhill back to Montepulciano.