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Italy trip advice

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Hi Guys -

First time on Fodors. Read these forums and lots of good advice. My wife and I are planning a trip to Italy in September. This is our first without 2 year old son in a while, so we are really looking forward to it. We are planning the trip from Sept 7th till Sept 20th. We have booked our tickets and flying out of JFK. Here is what we are thinking -

Sept 7th - Fly out of JFK into Milan
Sept 8th - Arrive early morning into Milan. Immediately take the train to Venice.
Sept 8th - 11th - Spend three nights in Milan. Stay at the Westin.
Sept 11 - Take the train to Florence
Sept 11th - 14th - Spend three nights in Tuscany.
* Day trips to Florence and nearby regions.
Sept 14th - Train from Florence to Rome
Sept 14th - 16h - Spend two nights in Rome. Stay at the Westin.
* I know this is not enough and won't do justice, but we are not big fans of crowded cities. Hoping to cover the "major" stuff in couple of days. Also, we arrive on Sunday. Would everything be closed?
Sept 16th - Train from Rome to Naples.
Sept 16th - 20th - Spend 4 nights in the Amalfi Coast Region.
* Not sure where to stay. Should we stay in Sorrento so we can day trip the area.
Sept 20th - Afternoon flight out of Rome back to JFK.

Few Questions -
For the Florence Tuscany leg -
1. Do you recommend staying in Florence for a night or two and then staying in Tuscany? The country side looks absolutely beautiful. And we normally don't like to hop around with our luggage, so would prefer to stay in one place. If we stay in Tuscany, can we just day trip to Florence/Pisa and other nearby areas in Tuscany? And lastly, which town in Tuscany should we stay in? Any recommendations on accommodations? We are willing to spend about upto $500 per night.

For the Rome part of the trip -
1. We arrive into Rome on Sunday. Will that be a wash? Again we are only looking to cover the major stuff in Rome.

For the Amalfi part -
1. Which town do you recommend? Should we stay in Sorrento, so we can explore all of the region? One of my friends recommended Positano. Any recommendations on where to stay? Similar budget as Tuscany (upto $500 per night).

This is our second trip to Europe. Any other advice you guys can provide would be very very very helpful :)

Thanks a lot in advance.

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