Train bookings in October

Tickets to where? Not all trains in Italy are reserved trains. Some are regional and cannot sell out and also are the same price at the last minute as they are the first day they go on sale.

Perhaps on busy holidays, some routes may be busier than others. Could some trains sell out? Perhaps. Maybe Trenitalia runs shorter trains off season when they know demand is lower, too.

I'd guess that your biggest regret will be paying more last minute for the fast trains than you would buying them early, because the "super economy" tickets may sell out early.. If you can live with that, I wouldn't worry much. If one train is sold out, you should find another.

Perhaps you can buy a few of your tickets in advance - the ones likely to be more expensive last minute and not others. If you book lodgings that at some point can't be changed, is there a big risk to buying the train tickets by that point?

This is a one month trip, so we're going many places, a variety of distances. You are actually confirming what I was thinking - that I should purchase the tickets in advance for the longer haul trips, not worry so much about the shorter trips (such as Milan to Lake Como).

Use http://www.trenitalia.com/tcom-en to research schedules and pricing. Be sure to use Italian city names, Roma, not Rome, Venezia, not Venice, Firenze, not Florence etc. You will get prompted for various stations in big cities. Anything designated as Regionale is unreserved, price-always-the-same type train.

Thanks - yes, I've been to that site. But it doesn't let me get to October. I tend to plan early (obviously) so maybe I just have to wait I'll about August to do the booking.

We (two people) trained around last October and only prebooked one train - the host wanted to know our arrival time. I found even the same day prices reasonable and there was plenty of room. We always had four seats.

you can also look at trainline.eu. Don't think much difference in prices if traveling city to city within italy. I'm like you in booking early and can't do it, I just registered with train line to send me an alert when available. Don't know what cities you will go to, just be patient. Which is not easy. Good luck and enjoy your trip
GO WARRIORS
Aloha Princess Pupule

You can compare prices for travel today or tomorrow with those for the same trips as far out as tickets are available to see what kind of disparity there is. Although Italian rail tickets are reasonable in general, there are substantial savings from booking Freccia tickets when they initially go on sale. And I have certainly seen trains marked as sold out when researching schedules for near-term travel options. Be especially careful if you're traveling around a holiday.

Although I wing my trips, making most hotel reservations just a few days out and buying train tickets quite late, there are obvious financial advantages to getting the long-range/fast-train tickets very early if you are confident about your timing.

To see prices you must Enter a date of travel within the next 120 days (trenitalia) and 90 (italotreno).
Trenitalia displays on-day prices as BASE, Italotreno as FLEX. Base and Flex are the top prices, you can't pay more.

Prices and schedules are set from June 11 to December 11.

All the other prices you'll see on the 2 sites are discounted and come with restrictions. Discounted tickets are also capacity controlled and sell out quickly. Odds are that 3 days before the departure all discounted tickets will be already sold out and you'll have to pay the BASE/FLEX price. There is no need to pay full prices in advance, get tickets just before getting on like everybody else.

Regional trains cannot sell out. All the other trains rarely sell out, if ever. It may happen in August, on Easter monday and before/after a long weekend, but it is extremely rare. I've never seen a trenitalia train completely sold out, there are always seats left in the most expensive classes.

People purchase in advance to save money, but note that those discounted tickets can't be refunded and changed.

P.S. Bear in mind that regionale tickets locally purchased must be time-stamped before getting on. From the moment you stamp it, a regionale ticket can be used on any similar train making the same run for a set amount of time. The validity period is usually 4 hours long, but there are local exceptions like the Liguria region. Forget to time-stamp and you'll be fined on the spot.