Milan or Taormina?

Taormina wins easily here. Below the town, Isola Bella and Mazzarò have clear water for snorkelling, though the beaches are narrow strips of pebble. Giardini Naxos and Letojanni have longer stretches of sand and shingle a short bus ride away.

Milan has no coast at all. Swimming means the Idroscalo basin, a city pool or a train to the lidos on Lake Como or Lake Maggiore. That makes it an occasional outing rather than something that shapes your day.

Milan eats better and more widely. Beside its own butter-rich classics, such as risotto alla milanese and cotoletta, it has serious fine dining, cooking from every Italian region and the aperitivo culture of the Navigli and Isola.

Taormina's Sicilian cooking tastes more of the south: swordfish, pasta alla Norma, granita with brioche for breakfast, and Etna wines. The weakness is depth, since the Corso leans towards tourist menus and there are fewer good everyday places to choose from.

Milan has far more to see. There is the Duomo and its rooftop, the Last Supper, the paintings at the Brera and Michelangelo's Rondanini Pietà in the Castello, with Sant'Ambrogio and the Ambrosiana behind them. The heritage comes in clusters among modern streets rather than as one old town.

Taormina has one world-class sight, the Greek theatre with Etna framed behind its stage, and a pretty medieval Corso showing Arab, Norman and Catalan influences. A day of slow walking covers it, and there are no major museums.

Milan offers a real night out. There are canal-side bars on the Navigli, the gay scene of Porta Venezia, dressy clubs around Corso Como and warehouse nights on the city's edges. It is well dressed rather than wild, and quiet in August.

In Taormina an evening means a passeggiata, a terrace wine bar and perhaps a piano bar, with a few beach clubs open late in summer. There is no club scene, and out of season the town goes quiet soon after dinner.

Taormina has the stronger outdoors, and it is close at hand. Etna's craters and lava flows are within an hour, and so are the basalt gorges of the Alcantara. Paths climb to Castelmola and Monte Tauro, and the Isola Bella reserve is good for diving and kayaking.

Milan itself is flat and often hazy, with Parco Sempione and canal towpaths for cycling. Its strength lies an hour to the north, where the lakes and the Grigne ridges offer good hiking and via ferrata for anyone happy to take a train first.

Both make good bases, but Milan is outstanding thanks to its high-speed trains. Verona, Turin and Bergamo are about an hour away and Bologna is not much further. Lake Como's villages, the Certosa di Pavia and Lugano across the Swiss border are all easy without a car.

From Taormina the east coast of Sicily offers fine days out, above all Ortigia and the Greek theatre at Syracuse and the black lava-stone baroque of Catania. Distances are longer, though, and the hill villages and Etna wine towns often need a tour or a hire car.

Milan is the easier choice with children, though neither city is built around them. The science and technology museum with its submarine, the flat centre, the trams and theme parks such as Leolandia and Gardaland give plenty to fill the days.

Taormina is welcoming but hard going with a pushchair, with steps and steep lanes everywhere and pebbly beaches that are crowded in August. School-age children will love Etna and the snorkelling. Families with toddlers often do better staying down in Giardini Naxos.

Milan is far simpler to get around. The centre is flat and walkable, the five metro lines are clear and take contactless cards, old orange trams fill the gaps and trains go direct to the lakes. The main drawback is the long transfer from Malpensa.

Taormina's centre is tiny and mostly pedestrian, but it is built on a slope, so every outing involves stairs. A cable car runs down to Mazzarò and the coastal railway reaches Catania and Messina. Etna and the inland villages, though, realistically need a tour or a car.

This is Milan's home ground. Via Montenapoleone and Via della Spiga hold the flagships of the Italian fashion houses, and La Rinascente and the Galleria add a long history. Design showrooms, boutiques in Brera and antique markets on the Navigli widen the range.

In Taormina the shopping is one street, Corso Umberto. It is good for Caltagirone majolica, coral, linen and Bronte pistachio cream to take home. Browsing is pleasant but the stock is aimed at visitors, and for serious fashion you go to Catania.

Neither is cheap, and they cost about the same overall. What differs is why prices are high and when. Milan is priced like a business city: rooms are hardest to find during trade fairs and fashion weeks, while aperitivo snacks and set lunches for office workers soften the bill.

Taormina is priced like a resort, with grand sea-view hotels setting the tone and costs peaking in summer. Sleeping in Giardini Naxos or Letojanni, or coming in spring or autumn, cuts the cost, much as staying near a metro stop outside the centre does in Milan.

Milan is one of the great opera cities. La Scala's season opens each December, and the city also has the Piccolo Teatro, a fine symphony orchestra and big summer concerts at San Siro. There is something worth booking for most of the year, apart from a quieter summer.

Taormina has one extraordinary stage rather than a full calendar. Concerts, opera and ballet in the Greek theatre, with Etna behind, make a memorable summer night, but the rest of the year offers little beyond chamber concerts and piano bars.

Both are fairly modest for wellness, in different ways. Milan has public bathing, with a well-known thermal spa complex with outdoor pools and saunas and the 1930s Bagni Misteriosi in summer. The city's pace is not restful, though, and for real calm you head to the lakes.

Taormina has no public bathing tradition, only hotel spas with sea-view pools and volcanic-mud treatments. What makes it restful is the slow pace and the views of Etna, best in May, June and late September when the Corso is quiet.