Climbing the steep hill to the centre of Cortona, I was struck by just how many American accents I heard en route that is, until I realised that this handsome town was the location for a much-loved book and film. Under the Tuscan Sun charted a year in the life of American escapee Frances Mayes and it was a big hit in the US a couple of years back (think A Year in Provence and you have the general idea). Since then, the Americans have flocked to this town, tucked away in the south-easternmost corner of Tuscany, with its slightly surreal flavour of 1950s Italy and Fellini.

They aren't disappointed and nor were we. It's an enchanting place with the bonus of stylishly individual shops lining narrow, cobbled streets that lead up to Cortona's historic centre. We found Venetian glass pens, hand-made paper in all hues and the kind of eclectic fashion shops that get you reaching for the MasterCard.

In its historic heart is the marvellously eccentric 18th-century theatre Luca Signorelli, named after Cortona's most famous painter. Adjacent to this was the perfect touch a gentleman's hat shop. Oh to be a gentleman!

The Cortona experience was a highlight of our stay in the region of Italy that's fondly known as Chiantishire by Brits who return every year, enticed by the pea-greenery of its unmistakable landscape, the gourmet food and, of course, the wine.

And then there are the historic hill towns. We were well placed for many of these from our base at Villa Cristallo. Booked via Meon Villas, this was a characterful house that can accommodate up to 20 people, set in a working vineyard near Montepulciano, one of the most splendid and highest hill towns.

Yes, we sampled the vineyard's wine: the red Vino Nobile of which the locals are so proud, the lighter, fruitier white wine and the dessert wine, Vino Santo, delicious when used to dunk an almond biscuit. We feasted by the pool on plates packed with tomatoes that tasted how they used to in our childhood, salty hams and the tangy local pecorino cheese then played at being restaurant critics on nightly tours of the nearby gastronomic eateries. We sampled ravioli filled with wild boar, saltimbocca veal rolled with ham and sage and, for the children, freshly-made pizzas.

By day, our trips involved driving through a verdant green sea with gentle waves rippling through it. Forgive me if I sound poetic, but the Tuscan countryside has a way of unearthing the Byron in the most verbally-challenged. Tall cypress trees march up the hills and encircle old palaccios the more trees, the grander the residence and everywhere are the vineyards, to either side of the switchback roads that lead you (slowly) around the region, raising a gasp at every corner as another jaw-dropping view comes into sight.

The most spectacular of these was in the Crete Senesi, the clay country southeast of Siena. Crests formed by the clay make this a dramatic desert of hills and ravines, broken only by dark green cypresses. Little wonder that the landscape inspired some of Italy's greatest painters. This is the scenic route to Siena, but then every road seems to lead there.

This is where our villa holiday turned into a city break or more accurately, a cities break. We started with Siena, famous for the mad bareback Palio horse race, ridden twice a year by ten competing districts. The racetrack is Siena's vast central Piazza del Campo, where locals and tourists congregate for what seems to be an all-day lunch in the numerous establishments that line the splendid shell-shaped square'.

Here the crowds were amused by a witty street entertainer. Sporting a business suit and red beret, this clown directed passers-by and pigeons alike, showing a red card to some, blowing the whistle on others. He helped' photographers, keen to get shots of the Campo's most famous landmark, the gothic Palazzo Pubblico, by pointing a mirror at their cameras and cooled down the hot and bothered with a water sprayer. It's clearly a daily show and an endearing one.

On to the sightseeing: Siena is packed with ancient treasures, many with the familiar ochre and sienna-coloured paint box colours for which the city is renowned. The Duomo, zebra-patterned inside and out, bucks the trend but gives its big brother in Florence a run for its money.

To the west of Siena, another city beats it hands down for the crunchy-bar effect of its golden buildings. In the Middle Ages more than 70 tall towers dominated the skyline of San Gimignano. Now just a dozen are left but they're still impressive, as much from the approach road as in the historic centre itself. Almost too perfect for words, San Gimignano is more compact and, thankfully, less steep than many of Tuscany's hill towns.

Closer to home, a hat-trick of hilltop towns kept us busy. Nearest to the villa, Montepulciano has a laid-back, lived-in feel. It's a labyrinth of tiny alleyways, out of which tiny cars, reminiscent of The Italian Job, dart and dive. Connoisseurs of fine wine rate Montepulciano's Vino Nobile among Tuscany's best and there's no shortage of wine-cellars in which to try them. There are plenty of fine palazzo and churches to explore, too, including the majestic Church of San Biagio, one of the finest Renaissance buildings in Tuscany But when it comes to wine, one hilltop town lords it over all others. Montalcino is a place entirely devoted to its local vintage, the famous Brunello red, with every establishment promising a tasting of high-rated, highly-priced wine. Even its castle, in the 14th-century Rocca fortress, has a wine cellar. There are formidable ramparts to walk, offering panoramic views over the southern Tuscan hills or you can see these from one of several Window on the World' wine bars, while sipping a Brunello.

Between the two, pretty Pienza is a different kettle of fish. Remodelled from a simple country village into a perfect small city, on the orders of Pope Pius II, Pienza has beautiful herringbone brick streets, sloping pavements and classical proportions and is almost entirely lacking in tourist traffic. It's also the home of Pecorino cheese and you can taste this, much as you sample the wines in other hill towns. We tried some at a nearby cheese producer and took home a car-load.

Away from city life, we found time to walk in the countryside. Beyond Chiancharo Terme spa resort we came across an old house with a grand wilderness of a garden and counted more than 100 cypress trees at its entrance. From here, a dirt track road leading to Chiarentana, with views of Monte Amiata, offered a refreshingly cool stroll among trees, the silence broken only by the birdsong.