Train help

I would go for the high speed trains if there is a significant time difference. Rail passes in Italy seldom work out cheaper than point-to-point tickets, so compare prices.

I think all of the trips you list would be high speed trains, not regional. They therefore give discounts for advance purchase, and the tickets are for a specific train. Passes rarely save money in Italy.

For a fuller answer, read this webpage: https://www.seat61.com/Italy-trains.htm

Hi. Do not buy a rail pass - extra hassle and not a good value in Italy. Look at trenitalia.com; set hour to 7 am to see all trains, use station names Milano Centrale, Roma Termini, Firenze SMN, Venezia SL. The 'base fare' is what you will pay if buy in Italy at last minute. Other choices:
- 'Bimbi Gratis offer'. Children under 15 get reduced rate if adults buy a full ticket.
- Super Econony fare - no discount for kids, but still may be even lower than Bimbi Gratis depending on train. However, note that the Economy fares generally lock you in to an exact date and time.

Example: Milan to Rome August 8 8:20 am 2nd class, which is comfortable:
Four full / base fares: 273 Euro
2 adults, 2 kids Bimbi Gratis: 182 E
4 Super Economy tix - no changes allowed: 150 E

Enjoy your trip!

Have you maybe considered:

Milan-Venice-Bologna-Rome-Florence-Milan or vice versa. It just seems odd to go Milan-Rome-Florence when Florence is between Milan and Rome.

Alternatively, maybe fly to Rome, then Florence-Bologna-Venice-Milan.

When even Rick says that rail passes rarely make sense for Italy, you know they are a bad deal. Even full priced tickets in Italy aren't that expensive, so it's very hard to make a rail pass pay off.

All of your routes will be served by high speed trains. On all but your last trip, you will have a choice of Italo http://www.italotreno.it/en or Trenitalia http://www.trenitalia.com/tcom-en. For Venice to Milan, Italo goes out of your way (via Bologna), so only look at Trenitalia on that route.

On both of these companies, the cheapest tickets bought in advance are non-refundable and non-exchangeable. If you don't take the EXACT train you are ticketed for, your ticket becomes scrap paper. The midpriced tickets can be "cashed in" for another ticket, but you pay any difference in price (in other words, you don't lose value). And the full priced tickets can be exchanged or refunded before travel, so there's no advantage to buying these ahead. Once the cheapest tickets for a train are gone, they don't come back. Full priced tickets are available until just before travel, unless the train sells out first (rare, but there are some reports of that on busy travel days).

Go to the websites of the train companies I gave above, and search for trains on your travel dates. Be sure to look for 4 tickets together and put in your childrens' ages. Use the Italian names of the main stations, even on the English language websites:

Milano Centrale
Roma Termini
Firenze Santa Maria Novella (Firenze SMN)
Bologna Centrale
Venezia Santa Lucia (Venezia SL)

If you don't mind the full price, you can wait until you get to Italy to buy. If you see a discount ticket and are sure of your travel schedule, buy now to get that price (discounts will definitely sell out).

EDIT: I see I was cross-posting with several others. You see that we all gave the same advice.

When you travel on high speed trains, you get "Bimbi Gratis", kids under 15 travel free when the adults pay the Base (full) fare. You have to buy these at least until midnight 2 days before you travel.
http://www.trenitalia.com/tcom-en/Offers/Bimbi-Gratis

All of the routes you mentioned are served by high speed trains so you likely won't be using Regionale trains at all.

Don't buy Railpasses as these don't include the seat reservations that are compulsory on the express trains. These are included with P-P tickets.

Although August is not far off, you may be able to save some money if buying advance tickets if you can find Economy or Super Economy fares (not likely in this case but you can try). The SE tickets are non refundable and non changeable once purchased.

You could also look for good fares on Italo Treno as they also operate on those routes. You can buy tickets for both rail networks at www.trainline.eu at the same price.

Tickets for express trains are specific to train, date and departure time, so check the train number before boarding. If you board the wrong train by mistake, you'll be subject to hefty fines!

Thank you this really helped. I know time is getting closer and trying to get all details finished.
Everyone getting very excited

We just returned from Italy and having the Trainline.eu app was incredibly helpful. No booking fees and up to date. I will never travel in Europe without it again.