Train Tickets vs. Rail Pass

Almost no advantage to railpasses in Italy; check advance-purchase fares; if you can commit to specific departure times, you can save tons (Milano Centrale to Venezia Santa Lucia for €9, for example).

Kajobrien,
You can actually save money if you buy discounted point-to-point tickets, up to 120 days in advance.

You can check train schedules & book your tickets on the Trenitalia website

You will need to choose the names of the train stations in Italian such as:

• Milan= Milano Centrale
• Florence = Firenze S. M. Novella
• Venice = Venezia Santa Lucia
• Rome = Roma Termini

You may find it helpful to read the man in seat 61 website which will explain everything you need to know about train travel in Italy (or elsewhere)

Enjoy!

For some reason it is cheaper to fly in and out of Milan. Our family of four save over $2000 by doing so. We had to travel all the way back to Milan from Belgium and extend our vacation by 2 days. But even with 2 additional days of expenses we still saved $2000 plus we got to go to the World Fair in Milan. You only have to travel from Rome to Milan. I would say the savings is worth it.

As the others have indicated using advance purchase, discounted tickets is usually a far more cost effective method for travel in Italy. Rail passes are rarely the most cost effective method for travel in Italy. I suspect this situation is far different than your last trip to Italy 19 years ago.

However there are some potentially expensive "caveats" to be aware of when using trains and other public transit in Italy. For example.....

• tickets for the fast trains (Freccia, Intercity) have compulsory seat reservations, and are specific to train, date and departure time, and can only be used on the one train specified on the ticket. Therefore if you buy advance tickets on those trains, you must be willing to commit to a specific departure. This is also the reason why it's generally not a good idea to buy advance tickets to connect with an inbound flight. It the flight is late or you're delayed for any reason and miss your train, the tickets are worthless. If you board the wrong train by mistake, you'll be subject to hefty fines which will be collected on the spot!
• Regionale trains do not require reservations, but if you buy tickets locally, the tickets must be validated prior to boarding the train on the day of travel, or you'll again be subject to hefty fines. You can also purchase tickets for Regionale trains online, and these will come pre-validated. Tickets for Regionale trains are the same price whether purchased in advance or on the day of travel.
• also note that the cheapest advance tickets are non-refundable and non-changeable once purchased, so be sure of the details before you press the "buy" button.
• tickets for Metro, Buses, etc. must also be validated as these are also subject to fines.

For the routes you'll be travelling, you can also use the competing Italo Treno high speed trains. If you decide to buy advance tickets, you can either use the rail network websites or https://www.trainline.eu/ (they sell tickets for both Trenitalia and Italo, at the same price as charged by the rail networks).

Thanks everyone. I think we will buy most in advance except for our arrival in Milan, wouldn't want to risk that!

We will be flying direct from California to London, then to Milan. Can you tell me if we will be going through customs in London or Milan? Our connection in London is only 1 hour... Maybe this should be in another message stream, but figured I'd throw it out there.

Thanks!

The heyday of the rail pass was a good 30+ years ago -- it is as obsolete as traveler's cheques.

Regarding your question on where you'll clear Passport & Immigration, my memory is a bit vague on that as I don't often go through London. With such a short connecting time and since you won't be stopping in the U.K., it's possible you may be directed right to your next flight, You will definitely have to go through Passport control in Milan, as that will be your first entry into the Schengen area, and your Passport will have to be stamped (that will be done again when you leave the Schengen area).

To get all the details of your transfer in London, plug all your flight information into this excellent Heathrow Connection Guide: http://www.heathrow.com/flight-connections.

Because most of the trains you'll take do require seat assignments, you don't have the hop-on convenience factor that a rail pass provides in some other countries. So it's only a benefit if it does save money for your particular route (more likely if you weren't able or willing to book well ahead).

Do you need to go to Florence before Venice? You'd have less backtracking and lower ticket total if you went to Venice first.