(One of the larger south Tuscan hill towns with attractive churches and palazzo, a good main square and famous red wine. Another town with exceedingly steep streets.)

Montepulciano lies to the east of Pienza. There are signs to car-parks at various points on the way up to the old town (where parking is restricted). There are many steep climbs within Montepulciano, so to avoid adding to them, go right to the top to see if there is space in the uppermost car-park before trying the others. It is best to find a car-park by the Fortezza, which is at the top of the town, rather than by the Porta al Prato at the bottom.

Montepulciano changed hands a number of times between Florence and Siena in the early days of its history, finally passing permanently to Florence in 1511. The Florentine rulers immediately set about making their mark by building a large number of grand palazzi and well decorated churches (some 60-70 years before the construction of neighbouring Pienza). None is outstanding, but most are worth a look (the main churches have good descriptive panels in Italian and English). The only real architectural treasure is just outside the town, the temple of St Blaise. The town's other great treasure is its heady, heavy red wine, the Vino Nobile di Montepulciano, said by many (but doubtless not by anybody in vinicultural rival Montalcino) to be the best in Italy.

If on a day trip, it is best to start with the town proper, and visit St Blaise (which is open all day) on the way out. If you enter by the Porta al Prato, it is a long haul up to the main square (Piazza Grande) and Duomo. The churches of Sant' Agostino and Santa Lucia can be visited on the way up. One comes first to Sant' Agostino (about 1427), with a fine façade trying to be purely classical but betraying the odd Gothic touch still: pointed arches and the ghosts of crockets in low relief above the door. Its designer was Michelozzo, who also made the attractive relief of the Madonna and Child above the door. An attractive classical interior, but with so much else to see, not worth lingering. Opposite the church, there is a tower with a grotesque figure who strikes the hours, more reminiscent of Germany than Italy.

After Sant'Agostino, turn up to the right to go up to Santa Lucia and on to Piazza Grande (by via del Poggiolo and via Ricci). Santa Lucia has an attractive travertine façade and inside, behind a grill on the right of the right hand altar, there is a rather tender beautiful tender-faced Madonna by Luca Signorelli (1441-1523).

Piazza Grande

Piazza Grande is an attractive main square, marred only by the unfinished façade and ugly campanile of the Duomo (although the campanile is actually 15th century and earlier than the rest of the Duomo, it looks more like a hideous remnant of Mussolini's time). The Palazzo Comunale, the town hall, occupies another side of the square - a handsome 14th century building with crenellations and a tower. The diminutive terrace below the tower is open to the public (small charge) . Enter by the main door and take the stairs up to the left. There are the usual panoramic views over the surrounding countryside.

On the other side of the square stands the Palazzo Cantucci (now selling local wines), one of the Florentine palaces. The bottom part was built by Sangallo the Elder, who was sent by the Florentines to fortify and embellish the town after it passed into their hands. The top floor was added later. The best building on the square is opposite the Duomo: the Palazzo Tarugi, also by Sangallo, with a grandiose baroque travertine façade, unfortunately marred by the filling in of the arches on the top floor to create more rooms. Sangallo also designed the well in front of the Palazzo, which must count as one of the most attractive wells anywhere, with its Florentine lions and Medici pawnbroker's balls matched by the Montepulciano griffon. Next to the Palazzo Tarugi stands the older but much restored Palazzo del Capitano del Popolo - Gothic windows to be seen clearly on the side going down the via Ricci.

The Duomo

Usually open all day.

From the outside, the Duomo (built in the early 16th century) is disappointing, with its unfinished, raw-looking façade. But it has an elegant classical interior giving an impression of coolness and space. It contains several paintings and sculptures of interest. On either side of the main door there are tombs surmounted by the figures of their occupants. The most distinguished is on the left and is by Michelozzo (1427-36) and belongs to Bartolomeo Aragazzi, secretary to pope Martin V. He is portrayed in gleaming marble, with a wonderful characterful face beneath a deep hood. The tomb was originally a much larger structure that was broken up at some stage. Other fragments of it are to be found around the church - two bas-reliefs on the pillars of the nave nearest the door; the two marble statues on either side of the altar; and the beautiful marble frieze immediately above the main altar table. Two other statues are in the Victoria and Albert Museum in London.

In the first chapel of the left hand aisle, there is a good polychrome terracotta altar (1512) by Andrea della Robbia, portraying saints Stephen, Bonaventura, Catherine and Bernardino. It frames an earlier 14th century marble relief. On either side there are strongly carved statues of St Peter and St John the Baptist, attributed to Tino di Camaino (1280-1337). Further along in the same aisle, between the third and fourth pillars, ther is a charming painting of the Madonna and Child - the Child with red hair and a beautifully painted robe - by Sano di Pietro (1406-81). Over the main altar there is a tryptich (1401) of the assumption by the Sienese artist Taddeo di Bartolo (commissioned during one of the periods of Sienese domination). Immensely colourful and crammed with figures, it gives a splendid overall impression from afar, but is a bit of a muddle close to.

Other sights inside the town

Distinguished Florentine-built palazzi and churches are scattered throughout the town. A little way down the via Ricci, there is a small picture gallery with some Sienese paintings (not of tremendous interest), open 09.30-13.00 and 15.00-18.00 except Monday and Tuesday. The main shopping street of the town is the Corso, or more properly via Voltaia nel Corso and via Gracciano nel Corso, running from the Fortezza at the top of the town down to the Porta al Prato. The church about half-way down, Gesu, has a baroque interior, although money appears to have run out when they got to the side altars which have trompe l'oeil pillars.

Montepulciano seems to have sprouted large numbers of fancy restaurants in the last few years. For good simple Tuscan food, go to the trattoria just inside the Porta al Prato, Diva e Maceo, well patronized by the locals. An alternative is to eat at the more sophisticated and expensive restaurant near St Biagio (it has a garden for summer eating).

Tempio di San Biagio

The temple (in fact a straight church) of St Blaise, just outside the town, is one of the best buildings of the high renaissance anywhere in Italy. In the form of a Greek cross, it was built of honey-coloured stone by Antonio Sangallo the elder between 1518 and 1534. Its beautifully carved interior encompasses almost every classical motif which the renaissance drew from ancient Greece and Rome - rather like a text-book exercise in renaissance design. Proportion and symmetry are all, going out of the window only in the failure to complete the second tower - what was it about the inhabitants of Montepulciano that made them incapable of completing their churches? - and the baroque angels high above the main altar, who are dangling their feet over the arch below in a most unclassical way. There is a good echo, especially from the central point. The only thing remaining from the previous church on the site is the rather battered 14th century fresco of Virgin, Child and St Francis immediately above the main altar - it had a reputation for working miracles, so was given pride of place in the new church.

The beauty of the church is enhanced by its setting, unusual for Italy, in the middle of a green field with a well and a nearby loggia (the Canons' house), both built at about the same time as the church.

1995, revised in 2003.