Going loony trying to pick itinerary!!! Help.
 

I didn't think planning my first trip to Italy would be this hard, but being that it is my first trip there is so much I want to see that it's hard to decide.

We are going September 29th. We will have 11 nights. Flying in and out of Rome. We have already purchased air fare. I would like to cover a lot of ground, but really would like to enjoy the local culture in each city we visit so I feel 3 cities is max for us. Do you agree?

I'm debating between
1. flying into Rome and getting the fast train ( since we will be so tired anyhow, we can just sleep) to start out in Florence 2 nights and then the Tuscany region for 4 nights, fast train back to Rome for the remainder.

2. Arrive in Rome, fast train down to Naples with a transfer to either Capri or Positano, than train back up to Florence, and finish in Rome.

What do you guys think! Thank you for all the prior advice you have given me!

Three cities is perfect. I like the first itinerary. I think the second is too much for 11 days.

Thanks so much for your opinion!

First itinerary seems very good to me.

From the second I'll skip Florence; I'll stay in Sorento and visit from there Capri, Positano, Pompeii, Naples

It seems easier to get to Florence than to the Amalfi coast (faster,less changes).

Another option is take the train to Orvieto upon arrival. Spend the night in the hill town and pick up your car for Tuscany the next morning. Drive from Orvieto to Montepulciano/Pienza/Montalcino/Siena/Chianti (whichever towns you planned to visit)and drop the car in Florence (airport), train to Rome.

I would follow kybourbon's plan. Orvieto is a nice place for an Italy newbie to start.

It's also possible to return the car in Siena and train to Florence, but the open hours of this office may be less convenient for your plans.