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  1. Journal
  2. Inspiration

Italy overland: a train-phobe's perspective

 Chris Dearden

Chris Dearden

7 Jul 2025 • 6 min read
Florence's skyline, with Brunelleschi's Duomo dome rising above the terracotta rooftops.

I’ll start with a confession.  I've spent the last ten years actively avoiding travelling on trains. Too many years standing on the 6.20 to Waterloo had made the notion of choosing rail travel as attractive as the limp sausage rolls that were my staple on the evening return journeys. Added to this, my latter-day life as a motoring journalist, with the privilege of regular access to some very nice cars, has made public transport a pleasingly rare necessity. 
 
And then my art-loving wife had a significant birthday coming up, and was owed a promised and much-postponed opportunity to examine at first hand the Renaissance art of Italy's galleries. I planned a trip taking in Venice, Florence, Rome and Milan. With a bit of luck, I could maybe even build a motoring article around it. I floated the idea, and as I'd hoped, received a rapt response. One tiny amendment."Why don't we do it by train?" Attempting to conceal my dismay (her birthday, her choice), I set about recalibrating the plan. 


Give me a journey, almost anywhere in the world, and I'll soon have a route worked out, taking in a curated balance of motorways, scenic roads and – where possible –  mountain passes, with coffee stops and overnight hotels built in. But trains? A quick look at European rail timetables reminded me of my introduction to econometrics as a fledgling undergraduate many years ago; serious help would be needed.  A half-hearted bid to revive the road trip on this basis was elegantly countered by my travel buddy:  "I’ve heard very good things about train booking agencies...". Resistance was futile. 

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Step in, Byway. After the briefest of initial requests, Jessi came quickly back with a suggested itinerary and the encouraging words, "Use this as a starting point and come back to me with any changes you'd like". She'd even built in suggested hotels. It looked very promising. I tweaked some times, gaining an extra morning in one city, or a bonus afternoon in another. I flicked between different hotels from the list of alternatives offered, and was impressed with how every potential change was immediately reflected in the total cost. 
 
When I was confident that the itinerary gratified my wife's requirement to maximise the number of Carravaggios, Raphaels and da Vincis we could view, I confirmed with Byway.  They swung into action behind the scenes, confirming trains, hotels and, vitally, reserved seats, guaranteeing there would be no reminders of that painful standing commute to Waterloo. 
 
Two weeks before departure, a detailed summary of all aspects of the trip arrived. It was similar to what I would normally produce, but without the many days of exertion and head-scratching on my part.  A snag, though. With the detailed schedule came the polite reminder that every train journey would need to be entered into the official Rail Planner app. I tried, I sulked, and then contacted Byway to request the paper-based option. Jessi gently reassured me that the app was more user-friendly than it seemed, and invited me to join the weekly Zoom conference where all would be explained. I did, and it was. In reality, the system works well when you've got your head around it. Knowing that you’re carrying all your travel passes on your phone actually generates a peace of mind I hadn’t anticipated, and we didn’t encounter a single difficulty at the barriers, as I’d (privately) anticipated.  
 

So, how was the trip? I have to admit, for a rail-phobe like me, it was a revelation. Trains were clean, air-conditioned and very comfortable. With a couple of notable exceptions, they left and arrived on time. Good food and drink were available on every journey. More intangible and unexpected was the camaraderie between passengers. Stories and chocolate were shared, and announcements were translated for the linguistically challenged (me). A philosophical approach was needed at times, such as when a stony voiced French guard announced that our train would arrive in Paris two hours late, because "cables have been stolen, and we are having to take a slower route". But planes are delayed every day, and a couple of months ago I was static for five hours on the motorway near Stuttgart.  It's a reality of modern-day travel. And five minutes after the missing cables were announced, a steward was coming round with free drinks for the children. 

The hotels were, without exception, excellent, in good locations and in every case with superb breakfasts – a critical factor. Even in this age of endless reviews, I often find that booking hotels can be hit-and-miss, but Byway has clearly chosen their selection carefully.  This just left arranging the galleries and places to eat in the evenings to me, and in Italy, this was never going to be a problem.  

I do have a few gripes. The wifi on trains proved at best spotty, and at worst non-existent. And of course, one thing that won’t change whether on Southwest Trains or cross-country in Italy,  grouped seats that face each other bring their challenges, not least the minimal legroom and the risks of footsie with strangers for the entire journey. I suspect it must be possible to specify other seats, though. And to be fair, one such seat arrangement allowed for a fascinating discussion on Canadian politics, with exchanged email addresses at the end. 
 

Did I miss having the car? I missed the flexibility, but I didn't miss the need to find overnight parking, nor the ever more complex emissions paperwork required in increasing numbers of cities. I saved over 100 gallons of fuel, and the resulting nearly 1000 kg of CO2 that would have been released into the atmosphere. And, of course, the luxury of being able to read, or have a snooze, or - if you really must - dig the laptop out and finish that report. Wifi permitting. 

All this said, my conversion has its limits. In a few weeks, I'm lucky enough to be heading back to Italy and wouldn’t swap the chance to do it in the Porsche convertible that’s mine for the occasion. But is the train phobia cured?  I’m slightly surprised to find myself saying that I really think it is. And if my wife suggests more international train trips in the future? No problem; I’ve got Byway’s number. 

 


  • #italy
  • #slow travel
  • #train travel

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