Lecce or Siena?

This is where the two differ most. Lecce is 12km inland, but the Salento coast is the reason many people come. The limestone coves and sea stacks of Torre dell'Orso are about half an hour away, and the clear, shallow Ionian sands of Punta Prosciutto take about 40 minutes. In summer, a morning on the beach and an evening in town is the normal routine.

Siena has no sea at all. The Maremma beaches are well over an hour's drive, so a swim takes the whole day, and most visitors make do with a farmhouse pool.

The two eat about as well as each other, and both stick firmly to their own region. Lecce's food is southern peasant cooking. You start the day with a warm pasticciotto and iced espresso with almond milk, and later eat ciceri e tria and fava purée with wild chicory, with dark Negroamaro to drink.

Siena's table is heavier and Tuscan: pici with duck ragù, cinta senese pork, wild boar and panforte from bakeries that have been going for generations. Its wine is the stronger draw, with Chianti Classico and Brunello poured by the glass in its enoteche.

Both towns are complete historic townscapes, but Siena has the greater art. Lorenzetti's Good and Bad Government, Duccio's Maestà, the Duomo with its Piccolomini Library and the Sienese school in the Pinacoteca can fill two or three serious days.

Lecce is Baroque rather than medieval. Its honey-coloured limestone is carved into fruit, beasts and cherubs on Santa Croce, and Piazza del Duomo glows at dusk. There is also half a Roman amphitheatre under Piazza Sant'Oronzo. Its pleasure is in strolling rather than in great collections.

Neither town is worth the journey for its nights out alone, but Lecce gives you more to do after dinner. Its old-town lanes are lined with wine bars and small cocktail bars, and on weekends students fill them for most of the year. Siena's university supports only a few pubs and wine bars, and its centre has gone quiet well before midnight.

Summer widens the gap. Lecce's dancing moves out to the open-air discos and beach clubs on the coast around Gallipoli, which means a drive but gives you a proper night out. Siena has almost no clubs nearby. Its one stretch of late nights comes with the Palio, when each contrada sets long tables in its own streets. That makes it a festival evening shared by the whole neighbourhood rather than a round of bars.

Siena has the finer landscape on land. The bare clay hills of the Crete Senesi and the cypress-lined Val d'Orcia begin close by. Strade bianche gravel roads lead straight out of town for cyclists, and walkers have the Via Francigena and the beech woods of Monte Amiata.

Around Lecce the plain of olive groves is flat, and the outdoors means the coast. There are clifftop paths from Roca Vecchia to Otranto, boat trips into sea caves, snorkelling and diving, and birdwatching at Le Cesine. Water lovers may well prefer it.

Siena has the better choice of day trips, with one of Europe's finest clusters of towns around it. There are San Gimignano's towers, Volterra, the Chianti villages, Pienza, Montalcino and Montepulciano, the abbeys of Sant'Antimo and San Galgano, and Florence about an hour and a quarter away by bus.

Lecce has a good spread of its own: Otranto's cathedral mosaic, island Gallipoli, white Ostuni and the trulli of Alberobello. The best of these are further apart, though. From either base, a car makes the outings far easier.

Lecce is the easier place with young children. Its old town is flat and largely traffic-free, and the piazzas fill with families in the evening. The shallow sandy beaches around Porto Cesareo are ideal for paddling.

Siena's steep, stepped lanes are tough with a pushchair. It works better for older children, who enjoy climbing the Torre del Mangia and watching the contrada drummers. Many families stay at a countryside farmhouse with a pool.

Lecce's weak point is getting beyond the town. Its flat old town is easy on foot, and fast trains run north to Brindisi and Bari. Across the Salento, though, the local railways are slow and infrequent and the beach buses run only in summer, so most visitors hire a car for the coast and the smaller towns.

Siena is better connected. Escalators climb from the station in the valley to the upper town, and buses run to Florence and the nearby towns. The price is the climbing, because its three ridges mean steep slopes and stepped lanes. In both towns, drivers park outside the walls.

Neither is a shopping destination, but what you take home differs. Lecce's craft is cartapesta, papier-mâché saints and nativity figures made in old-town workshops, plus carved limestone and Grottaglie ceramics. Siena offers more clothing, shoes and leather along Banchi di Sopra, along with majolica, contrada scarves and a large weekly market by the Fortezza Medicea.

Lecce is the cheaper of the two for most of the year. B&Bs in old palazzi are fairly priced, and street pastries and trattoria meals cost little. August is the exception, when rooms, beach loungers and a hire car all get expensive.

In Siena, the few rooms inside the walls are always in demand and jump in price around the Palio. The separate charges for the cathedral and civic museums add up. Staying at an agriturismo outside town helps.

The two are evenly matched, but the music is very different. Lecce's distinctive sound is pizzica, the tambourine dance heard at village festivals all summer, which peaks at the huge open-air Notte della Taranta in Melpignano. Siena's music is classical and jazz: summer concerts from the Accademia Chigiana in palaces and churches, Siena Jazz, and winter seasons at the Rinnovati and the Rozzi.

Siena is better placed for taking the waters. Rapolano's travertine pools are half an hour away. Further south are the steaming medieval bath at Bagno Vignoni, the free white pools of Bagni San Filippo and Petriolo's hot sulphur river.

Lecce has one main spring, Santa Cesarea Terme, with sulphur pools in sea grottoes under an hour away. Otherwise rest there means a spa at a converted masseria and the long afternoon break.