Siena or Syracuse, Sicily?

This is the widest gap between the two. Siena is inland, so a swim means the pool at your hotel or agriturismo, or a full day's drive to the Maremma coast at Castiglione della Pescaia or Follonica.

In Syracuse the sea is part of daily life. There are swimming platforms below Ortigia's sea walls, the sandy family beaches of Arenella and Fontane Bianche, rocky coves on the Plemmirio peninsula and undeveloped pale sand at Vendicari, about forty minutes south. From June to early October it is a real beach destination.

Both cook their own region and little else, but the two kitchens are very different. Siena's is food of the land: hand-rolled pici, ribollita, cinta senese pork and wild boar, panforte and ricciarelli. Its wine is excellent, with Chianti Classico, Brunello and Vino Nobile all grown nearby.

Syracuse has the edge, mostly because of the sea and the morning market on Ortigia. There, swordfish, tuna, sea urchins and capers become pasta with sardines, spaghetti alla siracusana and raw prawns. Add almond granita with brioche for breakfast and cannoli from the pastry shops, and eating becomes a larger part of each day's pleasure, though the choice is no more international.

Both are first-rate, and either deserves two or three days, but they belong to different eras. Siena is medieval: the Campo, the Palazzo Pubblico with Lorenzetti's frescoes of Good and Bad Government, the Duomo and Duccio's Maestà, all in a centre that reads as one Gothic city.

Syracuse goes back much further. The columns of a Greek temple stand inside the cathedral on Ortigia, the Neapolis park has the rock-cut theatre and the Ear of Dionysius, and the Paolo Orsi museum holds the finds, while the island's baroque lanes and a Caravaggio add later layers. Lovers of painting lean towards Siena, and anyone drawn to the ancient world towards Syracuse.

Neither is a place for clubbing, but Syracuse gives you more of an evening. On Ortigia an aperitivo by the sea walls leads on to small wine and cocktail bars, summer weekends run past midnight, and in July and August beach clubs on the southern coast add some dancing.

In Siena an evening means a long dinner, a glass of wine on the Campo and a few student pubs, and the town is quiet before midnight except around the Palio. Out of season both wind down early. For a big night out, Syracuse looks to Catania and Siena to Florence.

Siena's countryside is the more famous view. The clay hills of the Crete Senesi and the UNESCO-listed Val d'Orcia are best seen by bike on the strade bianche gravel roads or on foot along the Via Francigena. It is farmland rather than wild country, with no coast and no high mountains.

Syracuse has more variety. Inland gorges such as Cavagrande del Cassibile and the Anapo valley lead to pools and rock-cut tombs, Vendicari's lagoons draw flamingos, the Plemmirio marine reserve is good for snorkelling and diving, and Etna makes a day out. In both places the summer heat pushes walking into spring and autumn.

Siena has the richer choice of day trips, and more of them are close at hand. Florence is a bus ride away. San Gimignano, Monteriggioni, the Chianti villages, Volterra, Pienza, Montalcino and Montepulciano are all a short drive, with abbeys such as Monte Oliveto Maggiore and San Galgano between them.

Syracuse is a strong base as well, and its trips centre on the baroque towns of the Val di Noto: Noto, Modica, Ragusa Ibla and Scicli. Catania and Taormina lie to the north, and the mosaics at Piazza Armerina need a longer drive. In both regions a car opens up far more than the buses do.

Syracuse works better with children, mainly because the gently shelving sand at Arenella and Fontane Bianche gives every day an easy afternoon. Papyrus boat trips on the Ciane, the echo in the Ear of Dionysius and puppet shows on Ortigia break up the sightseeing.

Siena suits older children who enjoy climbing the Torre del Mangia and watching the contrada drummers. Its steep streets are hard work with a pushchair, though, and there is no beach to fall back on, so families there usually stay at a farmhouse with a pool in the countryside.

Siena is the easier place to get around. Inside the walls, nearly everything you will want to see is a few minutes apart on foot. Escalators carry you up from the station to the upper town, and buses run to Florence and some nearby towns. The cost is the steady climbing over its three ridges.

In Syracuse, Ortigia is flat and quick to cross on foot, but the archaeological park is a long walk or a taxi ride away. City buses are confusing for visitors and regional services are thin. Because of the beaches and the inland gorges, a hire car becomes close to essential.

Neither is a shopping destination, and most of what you take home will be food. Siena offers panforte, pecorino and wine, majolica and contrada scarves, Italian clothing and leather along Banchi di Sopra, and a weekly market by the Fortezza. In Syracuse it is Sicilian ceramics, coral and silver jewellery, linen and papyrus paintings, with capers, almonds and pistachio from the Ortigia market.

Syracuse is easier on a budget. Market sandwiches, arancini, granita and trattoria meals cost less than in central Italy, entry fees are moderate, and rooms on the mainland or outside high summer are good value, though Ortigia in August is not.

In Siena, rooms inside the walls are few and in demand, especially around the Palio, and separate tickets for the cathedral and the civic museums add up. Osteria lunches and an agriturismo base keep costs down. In both places a hire car adds to the bill.

Both have a modest programme lifted by one distinctive strand. In Siena it is music: summer concerts by the Accademia Chigiana in palaces and churches, Siena Jazz, and winter drama and music at the Teatro dei Rinnovati and the Teatro dei Rozzi.

In Syracuse it is theatre at its oldest. Greek tragedies and comedies are staged each late spring and early summer in the ancient theatre, a tradition since 1914, and Sicilian puppet theatre survives on Ortigia. For opera or an orchestra, Siena looks to Florence and Syracuse to Catania.

Siena is much the better choice for a restorative stay, thanks to the hot springs around it. Rapolano Terme's travertine pools are half an hour away, and there is the medieval bath at Bagno Vignoni, the free limestone pools at Bagni San Filippo and Petriolo's sulphur river, often paired with a rural spa hotel.

Syracuse has no thermal tradition and only spas in hotels and a few day spas. It offers a gentler kind of rest instead: long lunches and sunsets on Ortigia's sea walls, best away from the heat and crowds of August.