Rail from Zurich to Milan to Florence- Santa Maria Novella Station

First, rail pass will not pay for just two rail trips. You can find the schedule at bahn.de We did the reverse a couple of years ago -- Florence to Milan, overnight in Milan, next day on to Zurich. Beautiful ride between Zurich and Milan. You would buy your ticket through Swis rail because your trip is starting in Zurich. Should be easy.

You can buy advance-purchase discount tickets for the Zurich to Milan portion on the Swiss rail website, www.sbb.ch or www.rail.ch. The price is 25 to 30 CHF instead of the normal 86 CHF (this is in 2d class, which is fine.) The price includes the seat reservation. They are available 60 days in advance and you should buy them then as the discount fares are limited. You'll get a confirmation number that you show to the ticket agent in Zurich; he or she will issue the ticket. For Milan to fForence, you are probably fine just buying these at the station in Milan, especially if you take Frank's suggestion and spend a night in Milan. buy when you arrive for the next day. If instead you are going straight through with a stop in Milan, you might want to have the onward tickets in advance, especially if the connection time is short. Lately people have reported success with buying tickets on the Trenitalia website, so try that first. If that doesn't work, then RailEurope (not Eurorail) is a viable option for tickets on Italian trains. I have compared the prices many times, and each time RailEurope comes within a dollar or so of the Trenitalia price. You will have to pay the $18 handling fee, however.

OMG you guys are wonderful! Thank you so much for the much needed help. You have no idea how many glasses of wine I have to drink by the end of the day after trying to sort out the train info. lol

Assuming that you are arriving at the Zurich airport, the train station there is directly beneath the terminal area. It's called the Zurich Flughafen on the Swiss train website. If you begin your journey to Milan from this train station, it is most likely that you will be on a local train for about 12 mintues as you travel to the Zurich HB (main) train station. At this station, you will transfer to a nicer and faster EuroCity train to Milan. Total journey time is 4hrs03min.

And if you buy the discount tickets I mentioned, they are from the Zurich main station (Hauptbahnhof). You will need to buy a separate ticket for the short journey from the airport station to the Zurich main station. They are cheap ( a few CHF) but don't board that train without tickets! Most of the trains on this section are Selbstkontrolle, meaning honor system. They don't often check for tickets, but if they do, the penalty is steep if you are caught without.