With its medieval walled villages and ochre-coloured villas, set within a landscape of vineyards, cypress trees and hills rolling down to the coast, you could spend a lifetime exploring the best of Tuscany.

San Gimignano: Best for history
Once known as San Gimignano delle Belle Torri, or San Gimignano of the Beautiful Towers, there were originally 72 towers, 50 to 60 metres tall, crammed within the walls of this small, medieval town that crowns a hill in classic Tuscan fashion. There may be only 13 left, but they evoke a powerful feeling of time past. San Gimignano is probably the most complete and unchanged medieval town in Italy. The remarkable frescoes in The Collegiata, the Romanesque cathedral in the centre of town overlooking the Piazza del Duomo, give a sense of what life was like in the 13th century. Around the piazza also stands the crenellated Palazzo del Popolo, with its forbidding tower and loggia, and the Palazzo del Podestà. It is easy to imagine the piazza, and the steep, narrow streets leading into it, resounding to the clank of armour and clatter of hooves. Today, they echo to the tramp of modern invading hordes, three million tourists a year, armed with cameras and guidebooks rather than pikes and broad swords.

'I've lived here all my life,' says Maria. 'I'm almost as old as the stones. So many tourists these days. Now all the shops sell things to them or feed them.' The secret is to get here early, before 9am when the tour buses arrive, or stay on after they've departed, about 6.30pm, when you can stalk the streets like a medieval lord.

But you don't have to battle with bands of marauding tourists if you want to get a sense of medieval Tuscany. About halfway between San Gimignano and Siena is Monteriggioni, a small medieval village perfectly preserved within its walls, with towers at regular intervals. Monteriggioni owes its importance, and its walls and towers, to the dominant position that it held over the via Francigena, the ancient and vital trading road between Florence and Rome. Two magnificent doorways pierce the walls and there's access to sections of the walls that look down on the tiled roofs of the houses and their gardens. Monteriggioni, like San Gimignano, has a sense that the men in doublet and hose, ladies in wimples, peasants in jerkins and knights on horseback have just disappeared through the gates - and might return at any minute.

Further information
Visit sangimignano.com for details on the town.

Where to eat
Set about a mile back along the dirt road to Lucciola, Fattoria Poggio Alloro produces the ingredients for almost all its dishes at its farm, including pasta, cured meats, pigs, chickens, rabbits, Chianina cattle, wine and olive oil (00 39 0577 950153; fattoriapoggioalloro.com; via Sant'Andrea 23, 53037 San Gimignano).

Where to stay
Located at the end of a winding dirt road, four miles outside San Gimignano, the Podere Lucciola is lost amidst olive groves, vineyards, wheat fields and woods. It's an old farmhouse that has recently been renovated and opened for bed and breakfast. There are magnificent, sweeping views of the surrounding countryside all around. The nine rooms are large, comfortable and air conditioned, and there's also a swimming pool (£100; 00 39 0575 846119; italydreamvillas.com).

Siena: Best for campo life
Piazza del Campo, 8.30am. The sun is already warming the golden-ochre façades of the buildings surrounding it. A woman is pushing a baby buggy up a slope, while a delivery truck off-loads supplies to one of the many bars ringing the Piazza. There's the odd smattering of people colonising the tables, meditating over coffee and newspapers. Pigeons potter about the square undisturbed.

This is one of the most remarkable and beautiful urban spaces in the world. There is a feeling of immensity, of harmony and balance in spite of its irregularity. It rolls like the trough of a wave between two peaks. Paving stones radiate out in a vast, petrified fan from the 14th-century Palazzo Comunale (also known as Palazzo Pubblico) - with its bell tower rising 102 metres.

Piazza del Campo, 7.30pm. It's busy with people moving from one part to another like shoals of fish; one, twos, groups, families, pushing buggies, children chasing each other, talking on mobiles, talking to each other, shouting across the spaces. The tables at the bars - Bar Caffetteria al Mangia, Bar Manganelli, Bar Il Palio, Bar Fonte Gaux - are full. The scene is colourful, orderly, civilised. The tempo is mellow. But twice a year, on 2 July and 16 August, it will be very different. Piazza del Campo will be packed, bursting with 30,000 people crammed into every available space, balcony or rooftop to watch the running of Il Palio, as it has been run almost every year for the last 700 years. Il Palio is a magnificent medieval pageant culminating in 90 seconds of racing madness, when 10 horses representing 10 contrade - areas - of Siena, ridden bareback, speed twice round the oval track that runs inside Piazza del Campo. Each contrade chooses, and pays, its jockey champion, but none of the jockeys knows which horse he will be riding until the day of the race itself. In theory, this minimises the chances of doping, bribery and general skulduggery.

'They treat the horses much better than the riders,' says Lisa Fallon, who is married to a Sienese and has lived in the city for 13 years. 'It is absolutely a race for the Sienese, not for the tourists. It has real significance for us. It represents the rebirth of whichever contrade wins. And it is mind-blowingly exciting.'

Between the Titanic excitements of Il Palio, life in Siena, on the campo and in the steep streets behind it, continues at a reasonable, civilised pace. There's time for lunch and there's time for dinner. There's time for an ice cream and there's always time for a light refresher in one of the bars.

Further information
To climb Torre del Mangia, the bell tower adjoining Palazzo Comunale, costs £7 (10am-4pm Nov-mid- Mar, until 7pm mid-March-Oct). sienaonline.com has information on the city.

Where to eat
A lively trattoria a few steps from Piazza del Campo, Hosteria Il Carroccio serves up hearty Tuscan food packed with flavour. Highlights include crostini neri di milza (beef spleen on toast) and ribbolita (bean stew), (00 39 0577 41165; via del Casato di Sotto 32; closed Thursday).

Where to stay
The challenge in Siena is to find somewhere to stay inside the walls that is quiet and has its own parking. Palazzo Ravizza is the civilised solution to both problems. Originally a 19th-century family home, the rooms are very comfortable and reasonable sized, and have been decorated with immaculate taste. There is a small, beautifully situated and tranquil terrace garden and lemon house at the back, and the hotel also has an excellent English bookshop. It's conveniently located near the Duomo and is an easy walk to Piazza del Campo (from £100; 00 39 0577 280462; palazzoravizza.it; Pian dei Mantellini, 34, 53100 Siena).

Le Crete Senesi: Best for walking
While there's the odd outpost of village life in Le Crete, such as Mucigliana and San Martino in Grania, the region is more remarkable for its absence of human occupation; it lies either side of the S438, which runs southeast from Siena. Wandering through the area, you realise it's beautiful, but, well, different. Le Crete Senesi means 'Sienese clay', which helps explain the prevailing curious monochrome colour - warm grey, café-au-lait loam, cataracts of eroded soil, and abstract fields of wheat and sunflowers all without boundaries. There are steeply rolling, voluptuous hills seamed here and there with lines of trees, shaded by thicker pelts of woodland. These lines of cypresses stand like erect artist's brushes, tight and black against a sky that's as blue as the wing of a chalky blue butterfly before coiling across the side of a hill, marking the track leading to solid, handsome, muscular farmhouses. They no longer serve as farmhouses, but as the civilised retreats for rich Sienese, rich Florentines, rich Germans and rich English.

This is the landscape familiar from a thousand Renaissance paintings, the landscape we see when we dream of Tuscany, as if precisely ordered for the maximum aesthetic pleasure. Perhaps that's why it seems a bit weird: its openness, its perfection. The sensation is of being in a picture while looking at it. The particular nature of the countryside makes it ideal for walkers (there's a fine walk signposted from the road at San Martino in Grania) and cyclists.

Thirteen miles from Siena along the S438 is Asciano, a lovely town on the River Ombrone, with a splendid 19thcentury pharmacy and the Romanesque collegiate church of Sant'Agata. In June, Asciano holds the Sagra della Ranocchia, a festival that celebrates the frog as a gastronomic delicacy.

As Le Crete and now the S451 move a further 11 miles south towards the town of Buonconvento, which is tucked in behind massive 12th-century walls, the landscape begins to become more conventional. Dense woods take over from the beguiling hills, and olive groves replace the fields. It may be less striking than the barren landscape of Le Crete proper, but the beauty is no less.

Further information
For information on sightseeing, events and accommodation in Le Crete, visit cretesenesi.com (some parts in Italian).

Where to eat
La Brace in Asciano serves simple lunches from hand-written menus (from around £16; 00 39 0577 718056; Via Mameli 9, Asciano; Wed-Sun).

Where to stay
Located in Montepulciano, an attractive hill town south of Asciano, Agriturismo Ardene, a working farm, is the perfect base for exploring Le Crete and beyond. The elegant rooms have antique furniture, while fruit and jams served at breakfast are home grown (from £110; 00 39 0578 758648; agriturismoardene.it; Via di Valardegna 7, 53045 Montepulciano).

Montalcino: Best for wine
'To get the best quality wine, you have to start with the highest quality grapes, and that means the healthiest vines. And that means working with nature, not against it.' Francesca Padovani is an intense young woman when discussing her wines, but she breaks into a ready smile that illuminates the gloom of the cellar at Fonterenza like a shaft of Tuscan sunlight.

Francesca and her twin sister, Margherita, make Brunello di Montalcino. In the world of Italian red wine, Brunello di Montalcino has a certain cachet. More than a certain cachet. It is one of the most sought-after and expensive wines produced in Tuscany. And among producers of Brunello di Montalcino, Francesca and Margherita are remarkable, not only because they are young women in an industry dominated by older men, not only because 'we knew nothing about making wine when we started 10 years ago,' but also because they are producing all their wine from biodynamically (a kind of super-organic standard) managed vines. And that goes for their olive oil, too.

Their winery, Campi di Fonterenza, lies at the end of a dusty track that winds its way through thick woods below one side of Montalcino, a pretty hilltop village. Montalcino is all about wine. Neatly regimented lines of vines roll up to the very base of the houses. You can see where the wines are made in the cantinas in the surrounding countryside. You can drink it at any number of bars such as Campi di Fonterenza, Fiaschetteria and Fortezza in the narrow streets. And you can buy it at enotecas such as Pierangioli, Bruno Dalmazio and Di Piazza.

Brunello, itself, is a locally-specific clone of that classic Tuscan grape, Sangiovese. Its production methods are exacting - no Brunello will reach the market less than four years old, although there is the lighter and fruitier Rosso di Montalcino for more youthful, less expensive drinking.

A good many of the cantine - wineries - including Fonterenza, have tasting programmes. And should the spirit need refreshing after exploring the delights of the wines, the monks at the exquisite Romanesque Abbey of Sant'Antimo, just outside Sant'Angelo in Colle, a few miles down the road from Montalcino, sing the hours of service in Gregorian chant.

Further information
The tourist office, on Costa del Municipo 1, Montalcino, has maps, lists of vineyards and will help book hotels (prolocomontalcino.it, in Italian).

Where to Eat
The décor may be basic at Osteria Porta al Cassero - marble-topped tables, a stone floor, white walls - but the class of the food is unmistakable. Al Cassero celebrates classic Tuscan cooking - pici con le briciolie (home-made spaghetti with breadcrumbs), panzanella (tomato and bread salad) and scottiglia de cinghiale con fagioli all'uccelleto (wild boar stew with beans) - all produced to a high standard. It also has a wide range of top-class Brunello and Rosso wines (00 39 0577 847196; via Ricasoli, 32, Montalcino).

Where to stay
Set amid woods, olive groves and vineyards, Agriturismo Le Ragnaie, a farmhouse and winery, has elegant, comfortable rooms and apartments. Guests can hire bikes to explore the countryside, take part in wine-tasting sessions, tour the estate's wine cellar and enjoy traditional dishes at the restaurant - washed down with a glass or two of local wine, of course (£76; 00 39 0577 848639; leragnaie.com; Loc. Le Ragnaie, 53024 Montalcino).

Talamone and the Maremma: Best for the coast
With wild cattle and cowboys, pine forests and beautiful beaches as fine as golden salt, marshland and maquis, the Maremma is where Tuscany slides gracefully into the sea. It runs from Orbetello in the south to Livorno in the north - 93 miles of everything anyone wants to do with, by, under or on water. And just north of Orbetello, on the southern corner of the Parco Regionale della Maremma, is the small, beguiling port of Talamone.

It may not have the wild cattle or the cowboys, or the glitz and glamour of Orbetello, but in many ways Talamone is the whole of the Maremma writ small; a compact old fishing village hunched around a couple of piazzas with a sea wall guarding the ocean side. The harbour is packed with expensive pleasure craft but, says Massimo Palombarini, a local barman turned fisherman and windsurfing instructor, 'There are six boats still going out to catch the fish you get round here: sea bass, grey mullet, black bream. And three of the boats you can hire, to go to visit parts of the Maremma coast that you can't reach any other way. Or to dive or to fish. Whatever you like.'

He also explains why Il Golfo di Talamone is one of the best places in the whole of Italy for windsurfing. 'It's because the prevailing wind is from the west and when it blows, it gets channelled either side of that hill.' He gestures to the plump curve of a crest behind the port, 'and that directs it just perfectly onto the gulf.'

The same hill also marks the beginning of the Monti dell'Uccellina, a pine-forested part of the Parco Regionale della Maremma. It's criss-crossed with paths that lead through the spicy maquis, that distinctive Mediterranean mixture of bay, ilex and wild rosemary that cloaks the crest of the hill running parallel to the coast.

Looking back on this trip, I can't help but conclude that the genius of Tuscany is to have adjusted to the demands of the modern world without losing the beauty and richness of its past. Its hilltop towns and villages seem to have been modelled for visual perfection, but they function perfectly for the 21st-century traveller. Inside them lie some of Man's greatest artistic achievements. Around them lie some of Italy's most lovely countryside. Tuscany is a place to lose yourself not just for one weekend, but for a lifetime of them.

Further information
Parco Regionale della Maremma has a visitor centre in Alberese (parco-maremma.it; open 15 June-14 September).

Where to eat
Ristorante Da Flavia overlooks the harbour of Talamone. Most of the dishes are based on fresh fish and the wine list is impressive. Meals cost around £33 (00 39 0564 887091; Piazza IV Novembre 1, Talamone; closed Mondays in July-August).

Where to stay
Villa Bengodi, a 19th-century family house, overlooks the sea and is just outside Talamone. Set in 32 hectares of its own estate, it has large, comfortable rooms. Bed and breakfast only, but the homemade jams are worth the price of board on their own (from £80; 00 39 335 420334; villabengodi.it; Via Bengodi, 2-Loc. Fonteblanda, 58010 Orbetello).

The article 'The perfect trip: Tuscany' was published in partnership with Lonely Planet Magazine.