I am planning a trip to Italy with a friend. We are in our late forties and would like to see the major cities and also relax and drink some wine. We are coming from the USA. We would like to see: Venice, Florence and Elba Island, Rome Capri Island, and the Amalfi Coast and if we have time Sicily. I need help where to start from and how many days in each city. We will be riding the train and we'll have a driver in the South. Twenty days total with the flight days. We need some days to relax by the beach and just to sit and do people watching...Going in Sept 2014.

That's might be a bit much for 18 days. Do you have a list of your must see sites?

My first thought is: don't book your flights until you decide which places and in what order. Then book multi-city into one and out of another so you don't waste time back-tracking.

My second thought is that you have a lot of places in that space of time which means there isn't going to be much relaxing. Right off the bat I think you won't have time for Sicily unless you make the trip about the south of Italy only and do the Amalfi plus Sicily and maybe a few days in Rome.

What are your interests? That would help us to help you.

You have 3 major time-consuming destinations on that list- Rome, Venice, and the AC. I would assign a total of 14 days to those, leaving little time for the others---especially Elba.
I would start in Venice and end in Rome.

Including the AC, wouldn't it be advisable to fly out of Naples?

You'd need 2 weeks for Sicily so leave that for another trip. Also leave Elba off the list. You don't have enough time for all of this.

<< relax and drink some wine >>

I believe it's mandatory in Italy that you drink lots of wine!

Even if you limit your trip to Venice, Florence, Rome and the Amalfi Coast/Capri, it won't be very relaxing. With 18 days, you could spend 3 in Venice, 4 in Florence, 5 in Rome and 6 on the AC and Capri. When you include the travel time between stops, it is not awfully relaxed but definitely possible. With an itinerary such as this, I would fly into Venice, train to Florence, from there to the AC and end in Rome. Fly out of Rome.

Thank you so much for all your replies. I think we will leave Sicily and Elba out for another trip. We are doing the itinerary like mamcalice advise us. start in Venice, Florence, Amalfi Coast and then Rome. I will let you know how all turns out.

We will be riding the train and we'll have a driver in the South>

www.trenitalia.com is the official site of the Italian Railways - if you want to book far in advance you can get some nifty discounted tickets, which, sold in limited numbers can sell out long before the train and they have restrictions to on changes and refunds I believe but you can save a lot over just showing up.

For lots of great info on Italian trains check out these IMO fine sources: www.seat61.com - great info on discounted tickets - www.ricksteves.com and www.budgeteuropetravel.com - www.trenitalia.com can flummox novice users but there are always helpful Fodorites like kybourbon who posts above that know the ins and outs of the site and will come to your aid if you ask.

Last summer I had 14 days - and the Venice (although I cut that super short to see family) - Amalfi Coast (I did Positano) - Rome itinerary was wonderful and I think for the amount of time I had, it was the perfect trip!