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First time Italy: Much excitement and Some Questions

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Hello everyone,

My partner Robert(o) and I are travelling to Italy for the first time EVER! I have been silently (my friends, colleagues and family will tell you different) planning this trip for 15 months. We are now 7 weeks out and I am so excited I feel like I am holding my breath.

I had initially planned something quite insane in terms of hotel and place changes (after many versions and some mildly expensive cancellations and re-booked flights.. ah well)….. our pared down itinerary is as follows:

1.10 Arrive Roma in time for dinner (8.30pm) after 22 hour flight from Oz. We plan to eat and sleep or drink and sleep. (Hotel). I will see the Trevi fountain on my first night if it kills me. (It’s not too far from where we are staying).
2.10 Day in Roma to recover (from flight or drinks or both) and find out bearings.
3.10 Midday train to Cortona and spend week (villa small group bit fancy tour)
10.10 Morning train to Firenze (apartment)
17.10 Morning train to Venezia (apartment)
23.10 Morning flight to Palermo, collect rental and drive to Agrigento for night and next morning (Hotel)
24.10 After lunch drive to Taormina (B&B) stay four nights
28.10 Drive to Catania and fly to Roma for one week (apartment)
4.11 Fly home after lunch.

Our weeks are not filled in. We have lists/ research/options. And if, for example, we wanted to spend the night in Siena then we will. I have booked the Uffizi for our first night (Saturday) in Firenze, late night opening.

Questions
I do have some questions that I have not been able to answer despite my incessant/obsessive research and reading. Hoping you can help me.

In Australia, Optus offers a $10 per day global roaming unlimited calls and text and 50 MB of data. Has anyone used it? I will call them but just wondered if anyone had used this and if it was sufficient.

I am having problems booking trains and I would like to know the best site to book through.

Rob has attended Italian language classes and I can read many words in Italian but we are both pretty hopeless. Hoping emersion will work. The apps that translate speech and text look fabulous. Has anyone used it?

My birthday is 2 November All Souls Day following All Saints Day and a Monday so is that likely to be a closed day for businesses? It's Ok my husband can cook….but was hoping for something special.... lunch or dinner.

Ciao and Grazie.

Kym

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