Should we book train tickets ahead of time?

This question comes up a lot
Have you done a search here in the forum?

It’s best to wait
Get the Trenitalia (fast trains and regional) and ItaloTreno ( fast trains only) apps and get used to using them
Once you land and get thru passport control you can purchase your tix on the app
You can purchase the Malpensa Express tix to Milano Centrale on the Trenitalia app as well
Malpensa Express runs every 30 min and takes 54 min ( 10:13, 10:43, etc) so allow time for that and time to find your track at Centrale

For the Spoleto to Naples route it will be a regional train to Roma Termini then a fast train to Napoli Centrale
You could go ahead and get the Roma to Napoli tix- and take advantage of savings but that ticket won’t be changeable so allow enough time

For the regional ticket no need to purchase in advance, price never changes and they can’t sell out. You could purchase in advance- ticket is good for next 4 hours if you miss the train you have booked
Or just purchase at the counter- it’s a very small station
Trains from Spoleto to Termini run about every 45 min and take about 1.5 hours +-

Which car agency in Spoleto? We returned there years ago and Hertz is right across the street from station-about a block or 2-easy walk. Our only problem was nowhere to park so the agent took the car to park it elsewhere and we had to wait a bit but it the whole return was still only about 15-20 min

Get the Trenitalia and ItaloTreno apps and get used to using them

Christine, that is really good advice. Where were you 6 weeks ago? We didn't book Rome to Naples in advance eithe because of the fear of a flight delay. Once we got to the train station at FCO, 4 of the 6 ticket machines weren't working and the other two were being so fussy it was taking about 10 minutes per person to get tickets. The lineup for the 1 human selling tickets was extremely long; likely because of the wonky ticket machines. It took about 25 minutes to buy train tickets.

6 weeks ago I was on my way to Spain
I am not an app person at all but the Trenitalia app is so handy and so easy to use.

Sorry about your ticket kerfuffle!

Thanks a lot Christine! Very helpful! Will definitely download both apps! We will be returning car at Avis, it also looks minutes from the train station in Spoleto. Are the tickets for fast trains fluctuate in price depending on how much in advance they are booked?

Are the tickets for fast trains fluctuate in price depending on how
much in advance they are booked?

The price never changes but the discounted options sell out. (Economy, Super Economy, Me & You, etc)
You can always buy a Base ticket- full price- which is what you will be buying on day of.

You can look at your options for Aug 26 now. There's a fast train- Freccia 12:10 and 1:10-Base Ticket 56 euros.
Read all the conditions and offers
https://www.trenitalia.com/content/tcom/en.html

Milano Centrale
Firenze SM Novella

Helpful site:
https://www.seat61.com/train-travel-in-italy.htm.

Thanks Christine! Makes sense. I did look at both sites as well as Italo Treno to look at the options. Italo Treno has flexible option for much more reasonable price than Trenitalia.
I prefer to buy tickets when we are there , just was worried that they might be sold out. One of my coworkers said that tickets were sold out when he was visiting in July

It is very unusual for tickets to sell out unless it is a major holiday. Prices do not change. Trenitalia has a fixed number of tickets for sale at the Super Econ, and Economy level. Once all are solid for that train, they are gone. They do not release more later. Those tickets come with heavy restrictions so you need to be absolutely certain you are going on that train. In Italy we generally buy ticket as we need them. The base ticket is still pretty cheap.

Future readers: there is free wifi at FCO, you can get tickets via trenitalia's app at the airport when lines at the counter are so long.

he was visiting in July

which route? on a week-end? all trains from both companies sold out in all classes?

Thanks Frank! This is exactly what we will do - but when we arrive. Not sure which route Dario but was surprised to hear.