My work once sent me to the wrong side of Italy.
Usually they just give me cash and I book the transport myself. Someone in the office tho must have seen cheap deals for sleeper trains and just gone ahead and booked one. They booked me and my co-worker tickets on a Vienna-Milan sleeper train, then an early morning ticket to a small town called LegnaNo where we were supposed to be working. (Please note name of place).
The train turned up, and was an Italian train rather than an Austrian one. Italian trains are often shit. The cabin was horrible. Peeling old vinyl bunks, no aircon, and you had to share it with a load of strangers, and basically sleep on top of your valuables.
So after a crappy night’s sleep and 6am arrival on a Sunday at Milan station before anywhere to eat was open, we arrived in Legnano. We’d been given directions that the hotel was on the same street as the station, but we just couldn’t find it. I asked a local for directions. He had never heard of the hotel, and asked to look at the address. When he read it, he told me it was actually in a totally different part of Italy, and I should be in LegnaGo in between Verona and Venice.
So we went to the train ticket office. The ticket man told me it happened all the time- if you started typing “Legn” the train website defaulted to LegnaNo, a much bigger town. To get to where we should have been going on a Sunday required five different trains and a whole sheaf of seat reservations and tickets, and €50 of our own cash.
When we were finally on the last leg of the journey, we then got a €20 fine from a total jobsworth ticket inspector. Four of the five tickets were already stamped with a reservation time, but the final ticket for the last 10 miles or whatever had to be stamped at the ticket gate, and we hadn’t realised.
The kicker was that if I had arranged my own travel I would have been able to have a nice weekend in Venice, Trieste or Ljubljana and I would have been given expenses money for a hotel for Saturday night. Also had to hassle the office to give me the €70 in a timely manner.
I have always booked my own travel and claimed it back since, esp as the person in the office who does it now is basically fresh out of uni, not always the most full of common sense, and has never actually been anywhere much.