I'm still working up an schedule and I really need some advice/suggestions, mostly on trains and overall feasibility. I have not used the rail system in Europe or here for that matter so I probably making this harder than it has to be.

Basically I'm planning a whirlwind trip across Italy in 9 days. I plan to do:
3 days in Rome
Train to Florence
Day trip to Siena from Florence
Train to Venice for 2 days
Overnight train to Naples and from there see Pompeii
Train to Rome for and overnight stay and fly out

Now I know off the bat that this is kinda brutal but we are young and I think we can do it.

My questions are:
1. It looks like a rail pass may actually be worth it due to the amount of traveling. Right?
2. How would a pass work in conjunction with an overnight compartment? Would that defray the cost or is there extra? How would I reserve a space in that situation?
3. I'm actually looking to take the slower IC train in order to take advantage of the extra time to sleep. Is that a bad move? Any thing I should be concerned with?

Any other thoughts?

Thanks in advance.

Not knowing the times of your flights, or time of year or if you already have air tickets, this is how I would rearrange the days to optimize the trip. First, get an open-jaw ticket?fly into Venice and out of Rome.

Fly into Venice
Nights 1 and 2 in Venice

Train to Florence
Nights 3, 4 and 5 in Florence
Train to Siena one day

Train to Rome
Nights 6, 7, 8 in Rome
Train to Pompeii one of Rome days
Fly out of Rome on day 9

Alternatively, you could stay 2 nights in Florence and train to Siena and stay there for the night or eliminate Siena and add one day to Venice?of course, this depends on your preferences of what you want to see and do. Staying in just three cities gives you the option of taking the day trips to Siena and Pompeii, but if you decided not to, you will be in great cities with lots to do.

Also, if you do the cities in this order, the length of the train rides is shorter. Let's say you left a city to take the night train, that means you will be carrying your belongings with you all day, because checkout is usually around 11. That would be uncomfortable and why drag bags around if you don't have to?

Good advice from Lorac.

Go to www.railpass.com or www.railsaver.com and input the itinerary...it will tell you whether or not the passes are economical.

Passes become more economical the more you travel..in this case point to point tickets may be more economical.

You can, by the way, take a train from Florence to Siena for your daytrip although many prefer using the Siena bus because the bus station is slightly closer to the center of town than the bus station and sometimes you have to change trains in Empoli (which is easy since there are only two platforms).

I agree with the others that an open jaws itinerary would be more convenient.

If you have a rail pass that takes care of the basic "fare" on overnight runs. What the pass does NOT cover is the cost of any sleeping accommodation, be it in a six-berth couchette or a First Class single or double...those you would have to pay for in addition.

ANY seat reservation on any train in Italy would also cost extra to include those for Eurostar trains.

I would wait until I got to Italy to make any seat/overnight reservations if you are interested in getting these at the lowest possible price...do this at the first available rail station such as Venice...have your dates written out which helps. Otherwise, you can do it all through one of the pass agencies such as RailEurope or Railpass BUT if you do you'll have to pay their shipping and handling fees and sometimes they can jack up the price of certain items.

If this is the itinerary pace you want DON'T let anyone here dissuade you..it is YOUR trip and YOUR interests.

Have a great one.

I just did a whirlwind tour of Italy by train with my 2 kids, you can check out my trip report. I think you're better off not going to Naples from Venice. Add a day/night to Rome and do Pompeii as a day excursion, by bus or train, preferably with a tour guide. Remember, Pompeii is not right in Naples, it's another 45 minutes on a totally different train line-Circumvesuviana, not covered by rail passes. Depending how old you are, railpasses may not be worth it. Youth passes can be a good value if you're under 26; rail passes are not a good value on a trip like yours if you are over 26. Italian trains are pretty cheap, so point to point tickets may be better. Even with a rail pass, you need reservations (extra money) to be sure of a seat and on the highspeed (eurostar) trains, as well as for train sleeping accomodations. If you are the kind of person who can sleep anywhere, by all means try to sleep on the train, but be careful to lock your luggage to the luggage rack and take precautions with your valuables. You may find it works just as well to travel early in the a.m. or at a time that affords you a nap and a snack, such as 4 PM. You buy some food, board the train, eat a little meal, sleep a little, and wake up in your new city with time and energy to have dinner and explore. Open jaw tickets are good, but when we were looking at airfares, the price was prohibitive.

Forgot to mention that with rare exceptions (which wouldn't apply to your particular itinerary) seat and sleeping car reservations can only be made 60 days or less in advance.