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They don’t make railway stations like Milano Centrale anymore. This is, on balance, a good thing. Though Centrale certainly possesses a grandeur rarely grasped at by more modern, modest and utilitarian termini, it is magnificence of a sort that could be (extremely) charitably described as “old-school”. Centrale was opened in 1931 during Benito Mussolini’s dictatorship – and looks it. Among the decorative features glowering in marble and stone from its towering exterior and interior walls are eagles, winged horses, lions, gods, the helmeted heads of Roman legionaries and actual fasces: the ancient bundled-stick motif that passed into modern political language, via Mussolini, as a description of this kind of intimidatory architecture and more besides. Everything about Centrale seems calculated to declare that this is very much a station from which the trains will run on time, or else.

The time at which our train is running is 20.00 on a Tuesday night. We’ll be arriving in Palermo sometime around 16.30 on Wednesday afternoon. You could fly from Milan to Palermo in about 90 minutes. It wouldn’t cost you much, either. So why would anyone choose to spend 20 hours plus change making the same journey?

Trenitalia’s Claudio Calvelli has a ready answer: “People who like train travel; people who can’t fly for some reason; people on holiday who want to save a night’s hotel stay and arrive in the city centre,” he says when we meet prior to embarkation in the Freccia Club at Centrale. The lounge – for posher-class passengers – offers free wi-fi and drinks, and a measure of relative peace amid its curvy red-and-purple furniture. Calvelli estimates the custom of  Trenitalia’s Treno Notte (Night Train) services at about half foreigners, half locals – the latter cohort comprised of businesspeople, holidaymakers, families, soldiers and sports fans. Calvelli says that he only recently travelled overnight from Rome – where he’d seen his beloved Lazio lose their derby match to Roma – to a morning meeting in Turin. The Milan-Palermo service, he says, isn’t quite the pride of Trenitalia’s fleet – that is the Excelsior class of carriages found on trains running from Rome, which include restaurant cars and showers, and which the operator is about to soup up still further with new livery, wi-fi and an onboard intranet offering films and music. “But this is a great experience,” he says. “It’s one of the only services in the world where the train goes on a ship.”

An added enticement, to be sure, but an unnecessary one if you are one of those people who generally prefers the journey to the destination. And flying within Europe doesn’t count as any kind of journey at all: the continent all looks pretty much the same from the air and a couple of hours aboard a medium-sized airliner is never going to be a memory you’ll treasure or a story you’ll tell. The triumph of budget airlines, of the sort that will whip you from Milan to Palermo for barely more than the taxi fare to the airport, has vastly expanded the possibilities of travel. But it has also reduced once-proud flag-carriers to surly service, indifferent catering and less sense of occasion than a suburban bus trip, all of which is to say nothing of the dreary hassle of airport security. For all the rhetoric of freedom that we associate with the air, on a plane – especially short-haul economy – you’re basically baggage.

The same voyage done as long-haul rail travel, however, is excellent fun. The more so, ironically, since the backpackers who once populated these routes have substantially taken to the now-cheaper air, greatly lowering the risk of sharing carriages with people who travel with guitars and/or, in extreme and appalling circumstances, harmonicas. Compare the resignation of wedging yourself into an aeroplane seat with the anticipation and sense of exploration in opening a sleeper compartment.

Ours has an interior of dark blue and silver with faux-wooden panelling. It is perhaps two metres wide, maybe one-and-a-half across, though mirrors on both walls amplify the space. It contains three bunks, each already made up with proper cotton bedding. For daytime travel the top two of these fold into the wall and the lowest, with a certain amount of coaxing and swearing, can be converted to a not-uncomfortable three-seater sofa; ours faces backwards. As we prepare to depart, a uniformed attendant provides two small plastic bottles of water, one naturale, one frizzante.

Ingeniously secreted in the tight space are two overhead luggage racks, a ladder, three coathangers, a bin, a shelf, power points, individual lights for the bunks, controls for these and the air-conditioning and an enclosed sink unit. Once open, this yields three each of towelettes, sealed plastic cups containing fresh water and amenities kits in Trenitalia-branded paper bags. These contain toothbrush and paste, soap, allegedly refreshing face towel, two of what is either a paper toilet-seat cover or a starter origami kit to while away the hours, and a pair of white gauze-paper slippers. These prove of limited value as footwear but, with the aid of a marker pen, one of them could become a hand puppet with which to amuse restive children – such as the incessantly squeaking urchin a few compartments down – or a semi-imaginary companion, conversations with which could be protection against (or proof of) encroaching insanity as the journey unfolds. I decide to name mine “Silvio”.

We leave Centrale on time at 20.00. We get about an hour’s worth of the sort of bleak semi-industrial and suburban scenery that nobody comes to Italy for, and then the sun sets.

Sleeping on a train is a matter of persuading yourself that the lurches and wobbles are, in fact, a delicate, lulling rocking; that you are not in a bunk in a speeding vehicle but merely aboard a somewhat volatile hammock. I sleep a while not at all, then badly and erratically, and then so unrousably that I don’t even notice the discreet delivery of breakfast: a boxed pear juice, a cherry croissant, a fruit pastille in a Trenitalia wrapper and the morning’s edition of La Repubblica. For coffee I have to get up. The Milan-Palermo route has no restaurant car and is instead serviced by a caterer’s trolley – one that, unfortunately, can’t safely negotiate the egress between carriages and so is parked in a spare compartment a short way down the train.

Outside, the view rushing past is one of olive groves, grapevines and, in the distance, the Mediterranean. The first two stops are Vibo Valentia-Pizzo and Rosarno: at a bit after 09.00, we’re somewhere on the instep of the Italian boot. A sweep of the train’s corridors from front to rear yields no other tourists and few Italians, whose English is any better than my Italian. A couple of doors down from us is Danielo, a school administrator from Alessandria, already dressed for his Sicilian beach holiday. “The train is cheaper if you include what you save on hotels,” he says. “And I like the sea views.”

Any vexation that our compartment is on the wrong side of the train for these vistas is more than offset by the necessity of enjoying them by standing in the corridor outside, leaning on the bar across the window and watching as the foreshores of southern Italy unfurl in the morning sunshine. Most everyone else in the carriage is engaged in the same agreeably idle contemplation. Even the opera that is thundering from the laptop of the sociopath in the end compartment kind of works as an apposite soundtrack.

Mainland Italy runs out at Villa San Giovanni, where the train is to be loaded aboard a ferry for the crossing to Sicily, and where there’s a change of crews. Our carriage attendant from Milan, Gregorio, exchanges handshakes and says “Arrivederci” to everyone as he leaves. The ferry trip across the Strait of Messina takes about 25 minutes; getting a train on and off a ferry takes about three hours. The vessel that conveys us across the water, the Villa, is a dilapidated tub whose principal decorative features comprise fading posters, abandoned vending machines and disconnected televisions. The cafeteria on one of the upstairs decks is the first opportunity for a proper meal since last night’s (very decent) Milano Centrale gnocchi. Vexingly, all that’s on offer aside from chocolate and crisps is a cone-shaped battered-risotto outrage known as arancini, which isn’t the worst thing I’ve ever eaten but is the worst thing I’ve ever eaten in Italy.

Upon reaching the Sicilian shore the train is split. Some carriages head south to Syracuse while the rest, including ours, set off along the island’s north coast to its capital Palermo. So we’re still on the wrong side of the train to experience the sea views from the comfort of our compartment but once again on the right side to enjoy them from the corridor. This is hypnotically agreeable, as the tracks cradle the beaches approaching Capo d’Orlando. It is also, given that everyone else in the carriage has emerged to enjoy the same spectacle, an unusually sociable means of travel – notwithstanding the lack of any common language and the fact that the dog and cat someone has brought with them have woken up and don’t sound like they’re enjoying the ride nearly as much.

Retreating briefly into our compartment and looking out onto Sicily’s interior, I notice an intriguing hilltop village near Sant’Agata di Militello: a cluster of red roofs huddled on the crest of a forbidding escarpment. It looks like the kind of place I would like to visit one day and I make a note to find out more about it later. From the air I wouldn’t have seen it.

Palermo Centrale Station exhibits none of the hubris that marked our point of departure. It was apparently designed and built by people who were content to let a railway station be a railway station, rather than the architectural equivalent of a fist pounding a lectern. Or maybe it is simply that, by the time the terminal was opened in 1886, there was already a general recognition that there was little point in trying to compete with Palermo’s already-extraordinary riches in this regard. Among the happier legacies of being a vital port contested and conquered by pretty much every empire to have risen and fallen in the vicinity is a city whose food, buildings, art and people are as beguiling as its history. Raffish, chaotic, charming Palermo is perhaps the closest thing Europe possesses to its own Beirut: this is intended, lest there be any doubt, as nothing but the height of praise.

I have to fly home from Palermo to London. Via Rome, and including getting to and from airports, this takes about nine tedious, fretful, forgettable hours, hotel lobby to my front door. Thanks to expensive taxis, interminable queues, overstuffed shuttle buses, miserable departure lounges, a parsimonious seat pitch, tiresome turbulence and rattling Tube trains I find myself thinking that, by train, I could probably have made the journey in a couple of days: Palermo back to Milan, maybe on to Venice for the sleeper to Paris, then the Eurostar. I would have arrived home happier, better read and with further treasure deposited in the memory bank. I might even have gotten some work done.

Long-haul train travel is overdue a renaissance. Anyone who doubts that is probably overdue a long train trip.

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