Train ticket purchase timing....

Next time I travel in Italy I plan to buy tickets on the spot. Schedules change, strikes happen, my mood may change..... The downside of purchasing in the station is the time spent in line or possible difficulties in communication (have ticket info written down and show that to the ticket agent). I like to buy the ticket for my next train upon arrival at a new town. This saves time on doubling back to buy tickets. I do not usually buy a ticket just before time to board the train. In many cases, tickets can be purchased from machines. I do that sometimes.

Don't use RailEurope. Use the websites of the train companies themselves first (primarily Trenitalia but also Italo now for some fast trains).

http://www.trenitalia.com/tcom-en
http://www.italotreno.it/en

The Trenitalia site requires you to use Italian spellings of cities (Roma, Venezia, etc.) The site www.trainline.eu look easier to use and seem to be highly regarded by some travelers - and should have the same prices and allow you to buy tickets for both Trenitalia and Italo trains, but I've never used it.

The only tickets you might not buy in advance are the Milan to Cinque Terre tickets because of the uncertainty of your arrival time and possibility of flight delays into Milan. Some of the others might be regional trains (Cinque Terre to Pisa, perhaps), and those don't need to be bought in advance - they can't sell out and cost the same last minute as they do early. Rome to Venice I'd buy early for sure if you can still save money - the cheaper fares may already be sold out this late.

The fast Frecciarossa trains and IC train cheap fares can't be changed for free (if at all) so you do need to be firm in your plans. But it would seem you could at least pick Rome to Venice ahead of time...

The sites for ticket pricing and purchase are the actual train companies, Trenitalia.com and Italo.

These will offer discounts for advance purchase---Super Economy and Economy fares, which are substantially cheaper than Base fares. Trenitalia also offers free travel for children under 15 with the "Bimbi Gratis" ticket:

http://www.trenitalia.com/tcom-en/Offers/Bimbi-Gratis

These must be purchased in advance, wither online or at a station. they are only valid on Frecce and IC trains.

All these discounts are limited, and they do sell out.

I would definitely purchase Rome to Venice and Venice to Milan in advance, like now for October. You will have to check your actual travel days to see whether the Bimbi Gratis or Sper Economy tickets are the better deal.

For Milan to Cinque Terre, you will be on an IC train from Milano Centrale to Monterosso, so the advance purchase deals are available, but it is difficult to time a train with your arriving flight. That is, it is hard to know how much time to allow for arrival formalities and transfer to the central station, plus possible late arrival of your inbound flight. Allow too little time and you miss your train, and have to purchase new full-fare tickets. Allow too much and you spend a lot of time hanging around the train station when you are tired and jet-lagged. I am sure you will get lots of opinions on this, but my inclination would be, if the discount is substantial, to gamble a bit and buy the ticket now, allowing a reasonable amount of time for arrival and transfer. Be sure and check your flights for schedule changes first----and be aware it still could change, or your plane could be delayed.

use the official sites of the two competing companies actually running the trains: trenitalia.com/tcom-en and www.italotreno.it/en
Italiarail is a reputable US based re-seller for trenitalia, but they add a small fee and of course they won't display italo's trains and prices.

Trains do not sell out, there are still available seats on any Milan-Rome and Rome-Venice train departing today after 18:30! Today, in August, when the all country is going to or coming back from the seaside and the art cities... I bet you have nothing to worry about in October!

Discounted tickets, on the other hand, sell out and can't be bought on the day. You'll always find a seat at the last minute, but you will pay the full price.

There is a good reason for official sites forcing you to use italian city names: almost everything is written in italian and english in train stations except one thing. You won't read Rome, Venice and Florence on any sign.

Regionale trains like the one from Orvieto to Rome have no reserved seats and can't sell out. Regionale tickets not bought online must be stamped before boarding the train.

Rail Europe has most of the standard discounts that Trenitalia offers, but it doesn't have the Bimbi Gratis fare, so that's a good reason for your family to book on the Italian web site for longer rides, when you're ready to commit to dates and times. The Tarifa Familia is another offer you may see on the price chart when booking tickets.

Regional trains, which you'll take around the Cinque Terre and Pisa don't have any advance-purchase discount, so you can buy them in the station and pay half price for kids under age 12.

I have a few comments to add to the others....

To begin with, a few comments on car rentals. It's important to note that for driving in Italy, each driver listed on the rental form must have the compulsory International Driver's Permit, which is used in conjunction with your home D.L. (so you must carry both). These are valid for one year, and easily obtained at any CAA/AAA office (two Passport-sized photos required, which may be provided by the issuing office).

You may never be asked for an IDP, but failure to produce one if requested can result in fines on the spot! Failure to pay the fines on the spot can result in the rental car being impounded (which will result in further financial penalties). Have a look at https://www.ricksteves.com/travel-tips/transportation/rental-car-requirements for more information on I.D.P's and driving in Italy.

You may also want to have a look at some of the posts on the forum concerning the dreaded Zona Traffico Limitato (limited traffic) areas that are becoming increasingly prevalent in many Italian towns & cities (especially Florence!). Some of these are enforced by automated cameras and some by local police. Each pass through one of the automated Cameras will result in a €100+ ticket and visitors often don’t know of these violations until several months after they’ve returned home. In addition to the actual fines, renters will also be charged by the rental agencies for providing information to the authorities. You may find this website helpful - http://www.slowtrav.com/italy/driving/traffic_cameras_speeding.htm

Regarding your questions on rail travel....

• you can save money with advance purchase tickets for the express trains such as the Freccia or Intercity. However with that approach you must be willing to commit to a specific departure as the tickets are only valid for one train, date and departure time. Also note that the cheapest Super Economy tickets are non-refundable and non-changeable after purchase, so be sure you have the correct information when purchasing.
• you can certainly purchase tickets just prior to travel (or even on the day of travel) if you want to maintain flexibility, but you'll be paying Base Fare which is the highest pricing tier.
• tickets for the Trenitalia express trains usually go on sale 120 days from departure date.
• tickets for the express trains come with compulsory seat reservations, and you must sit in the assigned carriage (Carrozza) and seat no's (Posti), which will be on the ticket.
• you can also travel on the competing Italo Treno on high speed routes.
• you can purchase tickets either at the rail networks websites (Trenitalia or Italo) or at www.trainline.eu at the same price (no surcharges).
• you're correct that individual tickets are usually cheaper than a Railpass in Italy.
• there's no benefit to buying Regionale tickets in advance, as they're always the same price.
• as someone else mentioned, locally purchased Regionale tickets MUST be validated (time & date stamp) prior to boarding the train on the day of travel, or you'll risk hefty fines which will be collected on the spot!
• trains rarely "book up" in Italy. If that should happen, not to worry as there will be another one along in a few minutes. Regionale trains never book up, however you may have to stand for part of the trip.

Which of the five towns are you staying in the Cinque Terre? When buying rail tickets, you'll need to specify the name of the town in Italian as the "Cinque Terre" is not a rail destination per se.

I've always found the Trainline.eu website to be the easiest and most user friendly one to use, but registration on the site is required first. As they provide tickets for both rail networks in Italy that provides "one stop shopping", and you should be able to print out the tickets at home.

This community is amazing. Thank you for the input.

I already looked around the sites you all have suggested and it was much cheaper because of the Bambis Gratis fare. For example -- Milan Central to Montorossa, I found a fare of $65 for the 5 of us on ItaliaRail, but that was 41 euros (roughly $50) on trainline.eu. For Rome to Venice ItaliaRail was $212 compared to 135 euros (roughly $160).

One follow up question -- short trips like Orvieto to Rome I can just purchase at the station since they won't book up and I already see there is no Bambis fare, correct? I'll be sure to book the major routes -- Rome => Venice and Venice => Milan soon. I probably won't book Milan => Montorossa in the event of a flight delay (bummer, because they have Bambis fare). That just leaves Montorossa => Pisa. Should I book now or wait?

For anyone else reading this, www.trainline.eu seems to have a bit more intelligence built in than TrenItalia. For example, TrentItalia would book both adults in the more expensive Bambis Gratis fare, but trainline would only book 1 adult + the kids, then would book the other adult in an economy fare. In one case the difference was 25 euros. Ken -- it no longer requires registration to look around. I haven't booked yet, but plan to register before I do so that I have all the tickets recorded in one place. It also says there is an app now, which hopefully means I won't need to print tickets.

I'll post more as I make our reservations in case it's helpful to others.

" Ken -- it no longer requires registration to look around. "

Thanks for the comment. I posted on the assumption that the OP would be eventually buying tickets, so didn't make the distinction between looking and buying.

One additional comment. In my experience, it makes it easier to register payment details on the Trainline site if the credit card has the additional Verified by Visa or Mastercard Securecode (or whatever).