Tuscany

Lucca kept its independence as a republic for centuries, and its proudest monument is the ring of red-brick ramparts built between the sixteenth and seventeenth centuries to protect it. They were never tested in a siege, and in the nineteenth century the broad top was planted with trees and turned into a promenade. Today the walls, a little over four kilometres around, form an elevated park where locals walk, jog and cycle, looking down on one side over the roofs and towers of the old town and on the other over gardens and the Apuan Alps.

Inside, Lucca is flat, quiet and lovely to wander. The oval Piazza dell'Anfiteatro follows the outline of a Roman amphitheatre, its houses built into the old arena; the cathedral of San Martino and the church of San Michele in Foro have striped, arcaded Romanesque façades; and the Torre Guinigi has holm oaks growing on its summit. The composer Giacomo Puccini was born here, and concerts of his music are held in the town through the year.

TipRent a bike from one of the shops near the gates and ride the full circuit of the walls; it takes well under an hour at an easy pace.

When Pisa was a maritime power to rival Genoa and Venice, it spent the spoils of trade on a great religious complex on a lawn at the edge of the city. The Romanesque cathedral, begun in 1063, its circular baptistery and the bell tower together form one of the most harmonious ensembles in Europe, in white marble with bands of grey. The tower began to lean while it was still being built in the twelfth century, as its foundations sank into soft ground. Engineering work at the turn of this century reduced the tilt and stabilised it, and visitors can again climb the worn spiral stairs to the bells.

Most people come only for the photograph of themselves propping up the tower, but the rest of the square repays the time: the cathedral's carved pulpit by Giovanni Pisano, the baptistery's remarkable echo, the frescoed cloister of the Camposanto cemetery, and the museum of the cathedral works with original sculpture from the buildings.

TipClimbing the tower requires a timed ticket, which sells out in busy months, so book on the official Opera della Primaziale Pisana site rather than through resellers. Young children are not allowed up. Entry to the cathedral itself is free but also needs a timed reservation.

Perched on a high, wind-blown ridge between the coast and the Elsa valley, Volterra feels sterner and more remote than its neighbours. It was one of the great cities of the Etruscans, the people who ruled central Italy before Rome, and an Etruscan gate, the Porta all'Arco, still leads into town. The Piazza dei Priori is one of the most austere medieval squares in Tuscany, faced by a town hall begun in 1208. The Guarnacci museum holds a huge collection of Etruscan funerary urns and a strikingly elongated bronze figure known as the Shadow of the Evening, and below the walls lie the excavated ruins of a Roman theatre.

Volterra is also famous for alabaster, quarried nearby and carved in workshops around the town, and to the west the land drops away to the crumbling clay cliffs of Le Balze, which have swallowed churches and houses over the centuries.

TipVolterra has no railway station and the road up is winding; park outside the walls and walk in.

Seen from the road below, San Gimignano's skyline of stone towers looks like a medieval Manhattan. Rich merchant families built more than seventy of them in the town's heyday, as fortresses and status symbols, and around fourteen survive. The town grew wealthy on pilgrims and trade along the Via Francigena, then stagnated after the Black Death, which is why it has survived so complete. At its heart, the triangular Piazza della Cisterna, with its old well, opens into the Piazza del Duomo.

The Collegiata, the town's main church, is covered inside with fourteenth-century frescoes of Old and New Testament scenes, and the town hall has a painted council chamber and access to the tallest tower, the Torre Grossa, for a view over the vineyards that produce Vernaccia, a crisp white wine.

TipDay-trip coaches fill the main street from late morning to late afternoon. Stay overnight, or arrive early or in the evening, when the town empties and the towers glow at sunset.

Chianti is the hilly wine country between Florence and Siena, a patchwork of vineyards, woods, castles and stone farmhouses, and Greve is its unofficial capital and market town. Its unusual triangular piazza is lined with arcades, wine bars and a celebrated old butcher's shop, and on the second weekend of September it hosts a large wine fair. Just above the town, the tiny hilltop hamlet of Montefioralle is a perfect walled village of stone houses and lanes.

The Chiantigiana road, the SR222, runs north to south through the region and is one of the best drives in Italy, passing estates where you can taste and buy Chianti Classico, the wine with the black rooster on its neck.

TipMany wineries ask you to book tastings in advance. If you are visiting several, choose a designated driver, take a tour, or stay at an agriturismo that is also a working estate.

Radda is a small walled village in the high centre of Chianti, once the capital of the medieval League of Chianti, a defensive alliance under Florence. Its Palazzo del Podestà is studded with the coats of arms of past governors, and a covered walkway runs inside the old walls. The surrounding countryside is among the most beautiful in the region, with the medieval church of Badia a Coltibuono, now a wine estate, and the hamlet of Volpaia, a fortified village turned into a winery, both nearby.

Further south, towards Gaiole, the castle of Brolio is the ancestral seat of the Ricasoli family, whose nineteenth-century baron, Bettino Ricasoli, set out the formula from which modern Chianti grew.

TipRoads here are narrow and winding, and distances on the map take longer than they look; allow a full day just for this corner of Chianti.

Monteriggioni is a tiny fortified village on a low hill just north of Siena, built in the thirteenth century as a Sienese outpost against Florence. Its ring of walls, punctuated by fourteen square towers, survives almost intact, and the circle is so distinctive that Dante compared it in the Inferno to giants standing around a pit. Inside there is little more than a square, a church, a few houses and cafés, but you can walk along sections of the ramparts for views over the countryside. The village sits on the Via Francigena, and many pilgrims and walkers still pass through.

TipIt takes only an hour or so, making it an easy stop on the way into Siena. In early July the village holds a medieval festival.

Siena's great square is one of the finest public spaces in the world, a sloping, fan-shaped piazza paved in red brick and divided into nine segments, a reminder of the Council of Nine that governed the city's medieval republic. At its lowest point stands the Palazzo Pubblico, the Gothic town hall, and its slender bell tower, the Torre del Mangia. Inside, the Civic Museum holds Ambrogio Lorenzetti's frescoes of Good and Bad Government, a vivid fourteenth-century picture of city and country life, and Simone Martini's luminous Maestà.

Twice a year, on 2 July and 16 August, the square becomes the track for the Palio, a short, ferocious bareback horse race between the city's contrade, its historic districts. Each contrada has its own church, museum, flag and emblem, and the rivalries run deep all year round.

TipThe square fills to bursting on Palio days. If you prefer to avoid the crowds, visit in the days just before, when you can watch the trial races and the contrade's festive dinners in the streets.

Siena's cathedral is a striped marble masterpiece of Italian Gothic, its façade crowded with sculpture and its interior a forest of black-and-white columns. The floor is unique: over some two centuries, dozens of artists created a pavement of marble inlay showing sibyls, allegories and Bible stories. Most of it is covered to protect it, and it is shown uncovered only for limited periods each year. The Piccolomini Library has brilliantly coloured frescoes by Pinturicchio, and the pulpit is a masterpiece by Nicola Pisano.

In the fourteenth century the Sienese planned to make this building the transept of a vast new cathedral; the plague of 1348 ended the project, and the unfinished walls still stand beside the church. The cathedral museum, built into them, holds Duccio's great Maestà, and you can climb to the top of the unfinished façade for a view across the city.

TipA combined pass from the Opera della Metropolitana covers the cathedral, library, crypt, baptistery and museum; access to the roof walkways, the Porta del Cielo, is a separate, timed ticket in small groups. Check the official site for the dates when the floor is uncovered.

Montalcino sits high above the Orcia and Ombrone valleys, a compact hill town best known around the world for Brunello di Montalcino, one of Italy's most prized red wines, made only from Sangiovese and aged for years before release. Its fourteenth-century fortress, the Rocca, was the last stand of the Sienese republic after Siena fell to Florence and Spain in 1555, and today it houses a wine bar where you can taste local bottles, plus a walkway along the ramparts with views towards Monte Amiata.

The town itself is a pleasant tangle of steep streets, with a fine collection of Sienese art in its civic and diocesan museum. Dozens of estates on the slopes around it open for tastings.

TipRosso di Montalcino, the younger and cheaper sibling of Brunello, is an excellent everyday wine and is widely available by the glass.

In a quiet valley below the village of Castelnuovo dell'Abate, south of Montalcino, the Romanesque abbey church of Sant'Antimo stands among olive trees and cypresses. Tradition credits its foundation to Charlemagne; the present church dates largely from the twelfth century and is built of pale travertine and alabaster that glows softly in the light. Inside it is simple and serene, with carved capitals, including a famous one of Daniel in the lions' den.

The abbey is a living religious house, so visitors should be quiet and respectful, particularly when services are taking place.

TipA footpath of about two hours links Montalcino to Sant'Antimo through vineyards and woods, a lovely walk if you can arrange a lift back.

Bagno Vignoni is a tiny spa hamlet with one of the most unusual squares in Italy: instead of paving, its centre is a large stone-lined pool of steaming thermal water, fed by springs used since Roman times. Medieval popes and the Medici came here to take the waters, and the square is framed by an arcaded loggia and the small church of San Giovanni Battista. Bathing in the pool itself is not allowed, but the hot water runs down through old channels and mills to the Parco dei Mulini at the edge of the village, and several hotels and spas offer thermal pools.

Nearby, the walled town of San Quirico d'Orcia has a fine Romanesque church and the formal Horti Leonini garden.

TipFree natural pools below the village, where the water cascades down the hillside, are popular with locals; visit early or out of season.

The Val d'Orcia, the broad valley of the Orcia river south of Siena, is the Tuscany of postcards: bare, rounded hills of wheat that turn green in spring and gold in summer, lone farmhouses on ridges, and lines of cypress trees winding up to them. Much of this landscape was shaped deliberately by Sienese landowners in the Renaissance, who reorganised farms into an ideal, productive countryside, and painters of the Sienese school recorded it. UNESCO listed the valley in 2004 as an outstanding example of how a landscape can be designed.

Several views are especially famous. The little chapel of the Madonna di Vitaleta, between San Quirico and Pienza, stands alone with a pair of cypresses on a hill. Near San Quirico, a ring of cypresses rises from the fields, and south of Montepulciano, near Monticchiello, a road zigzags uphill between rows of cypresses.

TipMany of the best-known viewpoints are on private farmland or unpaved white roads. Stay on public roads and paths, don't drive onto fields or block gates, and go at sunrise or sunset for the softest light and fewest people.

Pienza was the village of Corsignano until a local boy, Enea Silvio Piccolomini, became Pope Pius II in 1458. He set out to rebuild his birthplace as an ideal Renaissance town and, in just a few years, the architect Bernardo Rossellino created a new central square with a cathedral, a papal palace and a town hall, all carefully proportioned. The cathedral is unusually bright inside, as the pope wanted, and the Palazzo Piccolomini has a hanging garden and loggia looking straight out over the Val d'Orcia.

Pienza is also the capital of pecorino, sheep's milk cheese, sold fresh, aged, or wrapped in walnut leaves or ash in shops all along the main street. Lanes with names like Via dell'Amore and Via del Bacio lead to the walls, where a walkway gives one of the finest views in Tuscany.

TipPienza is small and fills up at lunchtime. Come in the late afternoon and stay for sunset on the walls.

Montepulciano stretches along a narrow limestone ridge between the Val d'Orcia and the Val di Chiana, its main street climbing steeply past Renaissance palaces to the Piazza Grande at the top. The square, with its town hall, cathedral and a well decorated with lions and griffins, is the highest point of the town, and the town hall tower offers views as far as Lake Trasimeno. Many of the palaces have cool cellars carved deep into the rock, where Vino Nobile di Montepulciano, a noble red made mainly from Sangiovese, is aged and offered for tasting.

Just below the town, the church of San Biagio by Antonio da Sangallo the Elder is a perfect Renaissance temple of honey-coloured travertine, standing alone at the end of a cypress avenue.

TipThe walk up the main street is steep. Park near the bottom and walk up, or use the car parks at the top end of town and walk down.

Cortona clings to a steep hillside above the wide, flat Val di Chiana, near the border with Umbria, with one of the broadest views in Tuscany, across to Lake Trasimeno. It was an important Etruscan city, and the MAEC museum and the nearby tombs called the Meloni hold impressive finds. Its steep lanes lead between medieval houses to the Piazza della Repubblica, with a town hall on a grand staircase, and up to the Medici fortress, the Girifalco, at the top of the town. The Diocesan Museum holds a beautiful Annunciation by Fra Angelico, who lived here as a friar.

TipCamucia-Cortona station in the valley below has trains towards Florence and Rome, and local buses climb to the old town.