Portofino or Siena?

Portofino has no sand of its own, but the sea is right there. Swimmers climb down from rock platforms on the lighthouse path into clear, deep water, and Paraggi's small, sheltered bay is a short walk away, though paid beach clubs take up most of it. Boats run to the pebble cove at San Fruttuoso and to the beaches around Camogli and Santa Margherita.

Siena is an inland hill town. In town a swim means a hotel or agriturismo pool. Otherwise it is a full day out to the Maremma coast around Castiglione della Pescaia, well over an hour's drive away.

Both cook their own regional food: Ligurian pesto, focaccia and fritto misto in Portofino, and Tuscan pici, ribollita and cinta senese pork in Siena. In Portofino that mostly means a small cluster of harbour terraces where you pay for the view of the yachts and the cooking is solid at best, so people who care about food go to Camogli or the trattorie in the hills.

Siena rewards eating in town. There are family osterie in the contrade, old pastry shops selling panforte and ricciarelli, and enoteche pouring Chianti Classico and Brunello by the glass. Neither town offers much beyond its own tradition, but Siena's goes far deeper on the plate.

This is where the two are furthest apart. Portofino's main sight is the village itself, with its ochre houses round the harbour. Add the church of San Giorgio, Castello Brown and the abbey at San Fruttuoso, and you have seen it all in about a day.

Siena's whole centre is a medieval city on the UNESCO list. It has the Campo and the Palazzo Pubblico with Lorenzetti's Good and Bad Government, the Duomo with its inlaid floor and Piccolomini Library, Duccio's Maestà in the Museo dell'Opera, and the Sienese painters in the Pinacoteca. That is enough for two or three full days of sightseeing.

Neither town has clubs. In Portofino the evening is a dressed-up aperitivo and dinner facing the yachts, then very little, and outside July and August the village goes quiet early.

Siena has a little more going on thanks to its university, with a handful of pubs and wine bars and late glasses of wine on the Campo. Around the Palio, long outdoor contrada dinners keep the streets full until late.

Portofino's headland is protected on land and at sea. Trails through holm oak and pine climb to the Semaforo Nuovo viewpoint and drop along the cliffs to San Fruttuoso, with chains on some exposed stretches. Below, the marine reserve offers diving among red coral and seagrass and down to the Christ of the Abyss.

Siena's countryside is gentler and more open, with the bare clay hills of the Crete Senesi, the Val d'Orcia, and the strade bianche gravel roads that draw cyclists. It is lovely country for riding and walking, but it has no coast and nothing as wild as Portofino's sea cliffs.

Portofino is well placed on the Riviera di Levante. Camogli, Santa Margherita and Rapallo are close, Genoa is under an hour away, and summer ferries run to the Cinque Terre and Portovenere, so getting there by boat is part of the outing.

Siena has more within reach, and more variety: Florence, San Gimignano, Volterra, the Chianti villages, Montalcino, Pienza and Montepulciano, plus abbeys such as Monte Oliveto Maggiore and San Galgano. The catch is that most of these need a car, whereas Portofino's outings run on boats and trains.

Both are safe and calm, and neither has anything built for children, so the difference lies in what a family does there. In Portofino it is boats, swimming off the rocks and the walk up to the castle, with Genoa's aquarium as the obvious outing. The steep steps rule out a pushchair.

Siena appeals more to older children who like climbing the Torre del Mangia and watching the contrada drummers, and its streets are just as steep. In both places families tend to stay outside town, in Santa Margherita or Rapallo on the coast or at a Tuscan farmhouse with a pool.

Portofino is reached by a single narrow, winding road from Santa Margherita, about 5km along the coast, with very little parking at the end of it. A local bus runs that road to meet the trains, and from spring to autumn ferries link the harbour with Santa Margherita, Rapallo, Camogli and San Fruttuoso, which is the pleasanter way to arrive. In summer, though, the buses fill and the road jams. Once you are there, the village is only a few minutes across, apart from the steep paths up to the castle and the lighthouse.

Siena's walled centre is largely closed to traffic and spread over three ridges, so you walk everywhere, up and down stepped lanes between the Campo and the Duomo. Escalators carry you up from the railway station in the valley, and buses are the better link to Florence. A car left outside the walls opens up the hill towns. Trains are slow and infrequent, but Siena is still easier than Portofino to get to and to leave.

Neither is a shopping destination, and they differ in kind. Portofino's few lanes hold boutiques from big fashion and jewellery houses, plus resort clothes for people coming off the yachts, and you can see them all in under an hour.

Siena has more everyday shopping. Banchi di Sopra has Italian clothing, leather and stationery, and you can take home majolica, contrada scarves, panforte and pecorino. A large weekly market sets up by the Fortezza Medicea. Only for designer labels does Portofino have the edge.

Portofino is one of the most expensive places to stay in Italy. It has a handful of luxury hotels, drinks with a view cost a lot, and so do the loungers at Paraggi. Walking and the local buses are about the only cheap things, which is why many visitors sleep in Rapallo or Camogli.

Siena is much easier on the wallet. Rooms inside the walls are in demand, especially in summer and around the Palio, and museum tickets add up. Still, an osteria lunch with house wine is good value, and an agriturismo nearby can cut costs further.

Portofino has almost nothing here beyond the odd summer concert in the piazzetta or at the castle, so for opera you go to the Teatro Carlo Felice in Genoa. For a small city, Siena has a real musical life. The Accademia Chigiana holds summer concerts in palaces and churches, Siena Jazz adds performances, and the Teatro dei Rinnovati and Teatro dei Rozzi stage drama and music through the winter.

Portofino's calm comes from its pace in the early mornings, the evenings and the months either side of summer. The only treatments are in the hotel spas, and in high summer the midday tour-boat crowds break the peace.

Siena itself is no more restful, but it has thermal water nearby: the travertine pools at Rapolano Terme half an hour away, the medieval bath at Bagno Vignoni, and the free limestone pools of Bagni San Filippo. Combined with a farmhouse stay, that makes Siena the better choice for a spa-centred trip.