Tuscany by Car, or better yet, by Cabriolet (Italy)
We commenced our jaunt through Tuscany from Rome's Fiumicino (or Leonardo da Vinci) airport and headed north along the inland route. Our ultimate first day destination was a farm just outside Castellina in Chianti, but as is ideal for the region, we were not clock watching.
It takes a little over an hour and a half of relaxed driving to arrive at Orvieto and its really rather fascinating Cathedral.
The mosaic work on the exterior is really something to see, especially close up, as you try (almost in vain) to imagine the devotion that must have gone into laying every one of those tiny glass pieces all over the impressive structure. Inside is just as intriguing, the frescoes (including Luca Signorelli's Day of Judgment and Life after Death, compulsory study according to Michelangelo) are striking and even if you feel you have seen every church in Europe, you won't be disappointed wondering into this one.
Montepulciano is a compulsory stop, and that being the case we recommend making it your lunch location, specifically at Osteria Acquacheta for t-bone steak and the towns famous vino.
The historic town is a maze well worth exploring, and of course vehicles are not allowed, so ensure you have your walking shoes on.
From Montepulciano you are perfectly placed to explore the Val D'Orcia, a Unesco Would Heritage site, and an area of cultivated plains dotted with picturesque villiages.
Highlights for us, deserving of your visit include Pienza, Bagno Vignoni and the Abbazia di Sant'Antimo (the Abbey of Sant'Antimo).
Pienza was transformed by Pope Pius II who rebuilt it into the "ideal" or "perfect" town and the crowds it draws are testament to his success.
Bagno Vignoni ( (Thanks to the Via Francigena (which was the main route followed by pilgrims in antiquity who went to Rome), these thermal waters were found and have been used since Roman times. At the heart of the village is the "Square of sources", namely a rectangular tank, of sixteenth-century origin, which contains the original source of water that comes from the subterranean aquifer of volcanic origins. Since the Etruscans and Romans - as evidenced by the numerous archaeological finds - the spa of Bagno Vignoni was attended by eminent personalities such as Pope Pius II, Saint Catherine of Siena, Lorenzo the Magnificent and many other artists who had elected the village as their main holiday resort.
