Is there any specific conditions when booking sleeper trains in Italy
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Going to the official TrenItalia site as of today (end of April) for mid June:
I see there is essentially one travel solution where you first take a fast train from Florence to Rome and then a sleeper to Tropea (so I didn't bother checking for the return). You have to choose your type of seats/beds so make sure you get to this page by clicking on the price. Under "Service" choose either "cucette" (which I think is a shared compartment, either mixed "promiscuo", women ("donna") or the whole compartment "compart. intero") or "compartimento 3 letti" (a 3-bed compartment, "uomo" is men and the rest as above).
However, as you correctly point out, currently the next step produces "Error code: 439 Reservation not available. The train is temporary unavailable" and it is not possible to purchase tickets.
As of 02 May 2016 I can proceed to the next booking step for dates up to 13 June 2016 but not on later dates I tried.
This is very likely related to the upcoming change of train schedules and TrenItalia is not particularly good in updating all of it's train schedules that much in advance. The man in seat61 says:
Booking may open only 30-60 days ahead for travel immediately after the two annual timetable changes, on the 2nd Sunday in June and 2nd Sunday in December. Trenitalia is always late loading the data for a new timetable period, especially for regional, InterCity and international trains. ...
Similar info can be found on this website (in Italian).
I suggest you keep trying on a daily basis until you are able to book the ticket. Alternatively you could try with a travel agent that has more direct access to the TrenItalia system (but not sure they could do more).
(credits to @JoErNanO)
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