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Train from Lecce to Florence

Buongiorno! We will be traveling from Lecce to Florence in October. How far in advance should I book the tickets through TrenItalia? If I book now, do I run the risk of the train being cancelled? There are several departures for the day we plan to travel, but the ticket I'm interested in is 1/2 the price of the other departure times. Any advice is greatly appreciated! Grazie!