I've arrived in Messina by train - from the south, and from the mainland (the train rides on a ferry - you see nothing of the strait sitting for an hour or so buried in your carriage, but hear plenty of shunting-type noises); by road (the spectacular autostrada from north or south - but a nightmare once you leave it to descend into the hellish Messina traffic); and by aliscafo (hydrofoil) - from Lipari in the Aeolian Islands. Only the last can be recommended! Fly to Reggio rather than Catania, and take a hydrofoil. You'll arrive exhilarated rather than frustrated, crossing the Stretto into the great sickle-shaped harbour (hence its original Greek name of Zankle) guarded by a Statue of Liberty-like Madonna. Across the water, the city looks quite beautiful (make the most of it!), with the new cathedral of Cristo Re perched above it, and the precipitous pine-clad Peloritani mountains as a backdrop. [Similarly one should only ever arrive in Venice by vaporetto across the lagoon from Punta Sabbioni.]
The city was devastated by an earthquake in 1908, which killed 84,000 (most of the population) - so don't expect to see much that's old. Messina makes a virtue of its modernity - the traffic is lethal, and you may well spend much of your visit trying to cross the racetrack which runs north-south parallel with the shore. Where other Sicilian towns have a passeggiata on foot in the main square, in Messina this happens on motorini!
If you make your way northwards (stick to the shore) you will pass shops selling tempting things to eat and will eventually reach the museum housing treasures saved from the rubble in 1908 - noteworthy for two magnificent paintings by Caravaggio superbly hung to make the most of the famous shadows, and one of the rare works by local boy Antonello da Messina, the inventor of oil painting. You will be most likely be shadowed throughout by a guide, by the way. You can see the Caravaggios without the discomfort of going to Messina at this brilliant site: An Impossible Exhibition - The Complete works of Caravaggio.
Past the museum, you will eventually reach a beach from where you can look acrosss to Calabria and the White Mountain - and speculate whether Homer ever visited this quiet stretch of water constantly criss-crossed by ferry-boats: nothing about it says "Scylla and Charybdis"! You may be tempted to go further north to the point where the massive masts carry cables back to the mainland. Imagine what a bridge (first planned in 251BC by Metellus) will eventually look like. The bridge is now (April 2004) due for completion in 2015 - it will cost €5.6bn, which will be helped by EU funding. The span of the suspension bridge will be 3.2km, supported by two towers a quarter of a mile high (400m). Wow! If you get as far as Ganzirri there are some excellent fish restaurants (locally-caught swordfish a speciality: try it smoked if you can find it) - a very lively place in the holiday season, as is Mortelle a bit further on.
Back in the centre there are two things to see: the only church which survived (Chiesa Annunziata dei Catalani) - and the painstakingly rebuilt Duomo (it was restored after the earthquake, only to be flattened again by an allied bomb in 1943), with its impresive astronomical clock on the campanile. The fountain of Orion in the piazza in front is also worth a look. I also came across a small shop selling nothing but souvenirs of Mussolini and the Fascist regime.
A trip up into the hills is well worth it for the unbelievable views of the Stretto. You can walk or drive along the ridge through the pines for about 10k to the sanctuary of Monte Antenammare.
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