Hopefully someone will have a suggetion for the best way to get that night train reservation.>

If tenitalia.com can't do it then I'd try to do it in Zurich's Airport train station - if not then the first station in Italy. In the U.S. you would generally pay more to book it but it is possible if you are the type, like many travelers that want everything pinned down and ticket in hand before leaving - I always suggest the folks at www.budgeteuropetravel.com for any such reservation simply because they are experts and you can talk to someone via phone - very hard most places these days. Most likely you could even book the overnight train upon arrival in Milan but then you have just an hour or so before the train and if for some reason it were full, etc. Try trenitalia.com first for sure and it should be OK if kybourbon says so - I would bank on that! But I outlined other options as well.

>>>But are you comparing 2nd class fares to the 1st class pass?<<<

There is no class distinction on the night train so it would be a waste to buy a 1st class pass.

Second class is just fine on the Freccia Rossa trains and we must take in consideration also how much you would save by traveling in that class.

Here is an example:
ROMA TE 18:59
MI C.LE 02:59 9626 FRECCIAROSSA 114,00 € 89,00 €

The only time that I travel first class is when I take the IC(Intercity).

Thanks for all the replies everyone!

PalenQ: <But are you comparing 2nd class fares to the 1st class pass?> NO, I was comparing 2nd class for both. I got my rates from www.eurorailways.com for the 3 country Select Family pass with 5 train and 2 car days. I checked my individual fares from the Swiss Rail site, Trenitalia, and on www.Eurorailways.com.
It does seem like it will be cheaper to get the point to point tickets and just rent a car for the one or two days IF we decide to even take a day trip where a car would be needed.

I will look into preordering any tickets I can prior to leaving the US. If I can't for whatever reason, we can stand in line like anyone else...not that big a deal. :)

Once when I needed to reserve a night train ticket from Italy to Switzerland I called the American Express office in Venice and ordered my ticket over the phone. Someone at the office spoke English and my ticket was waiting for me when I arrived. I did have to pay for a call to Italy but I was very glad to have the ticket taken care of. I don't know how far in advance the office can book them but a call to an office would answer that for you.

Have a great trip!

<But are you comparing 2nd class fares to the 1st class pass?> NO, I was comparing 2nd class for both. I got my rates from www.eurorailways.com for the 3 country Select Family pass with 5 train and 2 car days>

Well since there is no Eurail Select Drive option I believe in 2nd class - that is if you are over 25 - folks over 25 can only buy to my knowledge a first-class pass - the pass you are comparing to is I do believ for first-class travel, which IMO is well worth the extra cost. I may be wrong if things have changed since 2010 about the pass only being first class if you are over 25 - perhaps you are under 26?

There is NO 1st or 2nd class on that night train which is their most expensive train and the pass doesn't include their sleeping compartment. Why pay for 1st class when it doesn't exist on at least two of her travel days?

Additionally, I think her pass calculations are way off. They would need the at least an intermediate car with 4 people and luggage. The price for that is $434 per adult for the first two + $334 for an additional adult (the 13 year old) + $167 for the child (if still 11 at travel time, if not, adult price kicks in). This pass is only for three rail days so there is an additional charge of $42 per person for each additional rail day ($336 for the two extra days). That's $1705 and seat reservations and sleeping compartment would still have to be paid.

You can purchase a 1st (about $1200 for the four)or 2nd class Italy (about $1000 for the four) Rail/Drive pass, but point-to-point tickets are cheaper and you would still need to buy the Swiss tickets, seats, etc.

Cars seems only to be used for small trips in Switzerland like Zurich to Bern and if going to cities why have a car at all - a liability once in a city like finding parking - large parts of these cities are off-limits to private cars, etc.

The only railpass I could think of considering would be a straight up Italian Railpass and I am not sure of that as I have no idea where Sapin is. Or it is Spain?

It's Sapri. A very small village south of Salerno. Basically almost all the way at the bottom of Italy on the West Coast. My father-in-law lives there 8 months out of the year.
The car I am only considering for 2 short trips in Switzerland, one to Fribourg area and one to Engelberg Switzerland. Only because the rail costs are about $200 for each of those day trips and both destinations are less than 2 hours from Bern by car. I plan to try and find out all the particulars about cars in the village and parking. Engelberg is a very popular destination even though off the beaten path, so I expect there will be some parking.

I plan to check into pre-purchasing any tickets about a month prior to us going. I will try the trenitalia site, and hopefully it will go through.

I am reconsidering the 2nd suitcase. If I can get all we need into one large one, I'll do it. I'd rather pay a little extra for an oversized suitcase than deal with an extra one on the 4 train trips we will have to lug it. Is that a bad idea?

Investigate buying in Switzerland for I think 25 Swiss Francs a Family Pass that will let the kids (all kids under 16) travel free on any train, lake boat, aerial cable car, etc. Buy it at a train station and your $200 per day cost should tumble dramatically.

If I can get all we need into one large one, I'll do it. I'd rather pay a little extra for an oversized suitcase than deal with an extra one on the 4 train trips we will have to lug it. Is that a bad idea?>

May be and may be not

One humungous suitcase can be hard to put into overhead luggage racks and even hoist onto and off trains - I've seen some really funny things about people trying those!

Maybe two manageable suitcases would be even better? Of course the class you are riding in makes a big difference as per space for luggage - lots more in first class IME.

PalenQ,

The $200 fares I searched were with the kids already riding free with the family pass. I had already calculated that cost into our total for trains. My father says he will check into what is the most economical because he can just go to the train station and talk to someone there. I am hoping the fares I have searched are all more than they will truly turn out to be...at least for Switzerland. Italy is already relatively inexpensive.