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Every day, to the clang of midday cathedral bells, signor Cuzzi creaks his way up Montepulciano’s cobbled streets to the Piazza Grande. It takes half an hour for his hunched figure to reach his seat in the piazza bar for lunch and a glass of Vino Nobile. As Cuzzi gazes at the panorama, he contents himself that everything on his plate – and in his wine bottle – comes from the valleys below. This is remarkable in two ways: firstly that at a hundred-and-three he is still able to see across a valley; and secondly that he credits his longevity to the local food.

From a stone bench on the front of Palazzo Contucci, I eavesdropped on the town’s centurion discussing his choice of dolce with the waiter. The palazzo stands on one side of the Piazza Grande - Montepulciano’s central square. Its singular acoustics are apparently designed to fuel local gossip, with conversations easily overheard from thirty yards away.

The bench was a waiting room for my appointment with the head of a family whose house I was sitting on: Montepulciano’s professor of wine, Almano Contucci. The Contuccis produce some of the town’s prized red Vino Nobile and - as Almano puts it - the family has been ‘rowing in rivers of wine for 1000 years’. Montepulciano owes its reputation as a city of art and viticulture to the Nobile: “Voltaire wrote about it in Candide and the poet Redi dubbed it the ‘king of all wines’,” enthuses Contucci. ‘Its name comes from the tradition of saving the best grapes for the nobles, but now we export it across the world’.

Some vintages, however, are still exclusive: Almano recently found a hidden cellar created by his grandfather during the war to stop occupying Nazis stealing the best wine. ‘We discovered a cache of bottles from 1887 which we open on very special occasions. The last one we opened was the ‘millennium bottle’ - now there are only seven left’.

In search of a setting to match the Vino Nobile’s high breeding, I headed down a shaded cobbled street toward the Antico Caffe Poliziano. Originally opened in 1868, literati such as Pirandello would sit on the balcony and gaze over to Lake Trasimeno. After the war the Poliziano’s fortunes declined - becoming a cinema before being completely abandoned. Reopened as a Café in 1992, it was – fittingly - given a visit of approval by the engineer of la dolce vita himself Frederico Fellini.

The bar upstairs is an ideal place to try local dishes. Montepulciano’s wine may be noble, but its food is rustic: country recipes fashioned from wheat, bread, oil, and beans. The local pasta is pici: fat, homemade spaghetti made from durum wheat - served with sauces which vary from one town to the next. My spicy tomato Pici alla Ragu tingled the tongue nicely while a side dish of bruschetta drizzled in sweet Tuscan olive oil cooled the palette. I followed this with a ribollita: a thick, almost solid vegetable and bread soup which has fuelled peasants though Tuscan winters for centuries.

There is one food which, whenever I mentioned it, brought tears of nostalgia to the eyes of the most hardened peasant: conserva di susine. Unique to Montepulciano, this plum jam was traditionally prepared by doting Italian mammas for sons titillated by the plum’s fruity nickname: ‘nun’s thighs’.

In an orchard on the edge of town the Peruzzi family have been ‘squeezing thighs’ to make this organic sugar-free jam for the last twenty-five years. The Peruzzi’s organic orchards keep Montelpulciano’s shops stocked with jarloads of conserve which locals buy to make their favourite snack: plum jam spooned onto fresh ricotta or pecorino.

The town’s great architectural feat is the Church of San Biagio. Best approached by walking the steep quarter mile down the hill, this heart-stopping renaissance church stands in a natural setting framed by lawns where it easily outshines all the baroque ecclesiastical fiddling within the city walls. I stood under the dome and clapped my hands to hear a remarkable acoustic echo which has bewitched pilgrims for hundreds of years.

As I drove through the wavy green knolls of the Val d’Orcia towards Pienza the landscape mellowed and the scent of aromatic herbs – with quaint names such as barbabecco (nose-peck) - filled the air. Pienza is a renaissance mini-city: built in a five-year homage to Pope Pious II, it is still virtually intact.

Pienza is also the capital of pecorino – known in the local dialect as cacio. The sheep that pasture the Val d’Orcia lactate a delicate and fragrant milk which is ideal for cheese; the result is cacio pecorino - mild, semi-seasoned and seasoned. The semi-seasoned matures in tomato paste, tinting the skin a tell-tale red, while the strongest cacio is conserved in walnut leaves giving it a dark colour.

Pienza seems to have more food shops than houses; local produce bursts onto the pavement, with peppers, artichokes, hams and cheeses wafting scented invitations to passers by. In recent years Cacio flavoured with herbs such as fennel has elbowed its way onto the pavement shopfronts - for some this is culinary profanity; but maybe the Pientini are turning back the clock to when the Etruscans - Tuscany’s mysterious ancient civilisation – first made ewe’s milk cheese with artichoke flowers.

Il Prato opened two years ago when local chef and restaurateur Riccardo Valenti converted a Pientine hay loft. Valenti’s restaurant serves traditional food in a classy ambience, with painstaking attention paid to finding fresh ingredients - so the dish of the house, Pasta al Tartufo, comes with different truffles according to the season. As I was in the cheese capital I decided to try the cacio in action and ordered an Insalata di Pecorino di Pienza. The fresh green salad was the perfect counterpoint to the milky unseasoned pecorino - a great a lazy lunch to eat on Il Prato’s garden terrace.

On the opposite side of the Val d’Orcia from Pienza is the medieval town of Montalcino. For years it was the focal point in a struggle between Florence and Siena and its military significance is marked by city walls and fortified towers. The 14th century fortress, known as the Rocca, is an ideal entry point into the town’s history and gastronomy. The Rocca is home to an enoteca where I ate al fresco and sampled the most compelling reason to visit Montalcino: the world class Brunello wine.

The Brunello is one of Italy’s greatest, most long-lived and wallet-tapping red wines. Fanatical oenophiles arm themselves with a list of the 141 producers from the Consorzio del Vino and treck round the vinyards in search of their favorite. I took a more relaxed approach by chatting with the local restaurateurs to find out which Brunello they serve.

Those with a sweet tooth and a romantic soul can buy a bottle of Vin Santo (dessert wine) and then pitch up at Mariuccia’s pasticceria. This family run shop has been dispensing some of Tuscany’s finest biscuits since 1935 when La Mariuccia set up shop here. Grab a selection of Ossi di Morto – the bizarrely named but delightfully crumbly ‘dead man’s bones’ – and some of pasticceria’s own-recipe biscuits and picnic on a vantage point on the city walls and gaze across southern Tuscany.

To the north of Siena is San Gimignano: the medieval Manhattan. The nickname comes from stone towers erected in the 12th century by the town’s powerful families. Seven are still standing - from a distance they stand like giant sundials, their shadows twirling round the hillside.

Only one tower is open to the public. Fortunately this is the tallest, the Torre Grosso. I just about had enough breath to make it to the top to be rewarded with a vision of medieval urbanism. The streets of San Gimignano fan out below, while beyond the countryside revels in its beauty; green fields, dotted with impressionist flecks of red poppy and yellow rapastrella, are marshalled by rows of cypress trees grouped like pilgrims to an Elysian landscape.

This fertile terrain means San Gimignano’s shops are bursting with food for all seasons. I visited Mauro Ghini and Ornella Capizzouli owners of La Buca di Montauto, which brings together the best in local produce. Nearly everything in the shop is produced at their farm: ‘from the earth to the counter’ insists Mauro. Stuffed wild boar stand guard at the shop entrance marking the fact that this was the town’s first salumeria di cinghiale. Mauro and Ornella also produce a heavily flavoured Senese ham, an olive oil with a typically Tuscan sweet and delicate texture and their own vintage wines.

To mark my last evening Tuscany I headed to La Collegiata. This renaissance palazzo on a hill opposite San Gimignano was once home to an order of Franciscan monks. The monastery’s former chapel is now a restaurant and it is worth eating at just to marvel at the service. Waiters whisper in cabals, forming strategies to bring a dish to your table, all under the orchestration of Maitre D’ Salvatore Roccoro whose four stage wine service is an act of oenic performance art.

Fortunately the food lives up to the setting and delivery. My artichoke salad was sprinkled with fine chopped pecorino and nuts, while the main course of asparagus rolled in laser-thin steak was flavoured with a lusty pepper sauce. The dessert was pure culinary aesthetics: individual spun-sugar moulded shells each one cradling a different flavour of ice cream.

San Gimignano is famed for its Vernaccia. This is Tuscany’s great white wine, whose roots go back 800 years to when Dante wrote about the gluttonous Pope Martino who stuffed himself with eels alla Vernaccia and ended up in purgatory. I ended up in heaven when Salvatore brought me two vintages of Panizzi Vernaccia – the fresh and fruity basic and the more weighty golden reserve which is aged in oak. The perfect goodbye toast to Tuscany.

There is an Italian saying: tell me what you eat and I’ll tell you where you’re from. There is no better way to discover this bond between food and landscape than the hill towns of Tuscany: anything that they can’t see or smell from the hilltop is not to be trusted. What grows around here is food for a lifetime - which, if signor Cuzzi is anything to go by, seems to be around a century or so.

FACTBOX

Montalcino.
Osteria di Porta Cassero. This popular trattoria is run by ex-barber Piero and his family . 9 Via della Liberta. Closed Wednesday.

Enoteca della Fortezza. There is no kitchen here, so be prepared for a raw lunch of cheese, bread and salami plus copious glasses of Brunello. Open daily 9am-8pm. Head for the fort in Piazzale Fortezza.

Wine: Arm yourself with a list of Brunello producers from the tourist office or Consorzio del Vino (Costa del Municipio). On the back is an appraisal of the annual vintages. Empowered by your new found wine buffery - 1990 and 1995 were outstanding but if someone tries to fob you off with 1984 just say no - you are ready to tour the vineyards in the surrounding countryside. For the less bibulous, bottles can be bought in enoteche around town: Barbi, Caparzo, Villa Banfi, Salvoni are good names. Opinions on Brunello flow as freely as the wine in Montepulciano, but a good bet is to ask restaurateurs for an upsum on the current state of play. If you’re here on a Sunday head to the Civic Museum - housed in a former convent - for the weekly glass-and-cloisters tasting in the presence of some extraordinary devotional art.

Marriuccia. The Montalcinese biscuit emporium. Try the Ossi di Morto, Dandi and Rustaci di Montalcino. 29 Piazza del Popolo

San Gimignano
Dorando is an intimate restaurant located off the Piazza Duomo. Marcello Bisogni and the chef Duccio Ferri spent a lot of time researching Etruscan, Roman and Medieval cuisine before opening. 12.30-2.30pm 7.30-9.30. 2 Vicolo del’Oro. Tel: 0577-941862 La Buca di Montauto. (see text) 9am-8pm. 16 Via San Giovanni. Tel: 0577 940 407

Gelateria Di Piazza. Sergio Dondoli is the laughing ice cream maker whose shop has gained legendary status. While on his Tuscan holidays Tony Blair dishes up cornettos to his family from Sig. Dondoli’s parlour. 4 Piazza della Cisterna.

Wine: In 1966 La Vernaccia was the first wine to be awarded DOC (Denominazione di Origine Controllata) status. There is a strada del vino (wine trail) and the tourist office will give you a leaflet and send you on your way around the producing vineyards. Try the Panizzi – both the basic and the reserve which is aged in oak.

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