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Request for Itinerary help - first time in Italy

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I will be traveling solo in Italy for 12 nights in mid October and would love a little advice. I am flying in and out of Rome and have pretty much narrowed down my wish list to spending a few days in or near Florence (maybe 3 or 4 - possible day trip to Cinque Terre if weather is conducive), several days in Tuscany (maybe South of Siena, Pienza or near Cortona - 4 or 5 nights), and a few days in Rome (4 or 5). I'm looking for a combination of seeing museums and some churches, but also reserving plenty of time for just enjoying being in Italy, watching the world go by and enjoying the experience (in other words - I am not looking to pack my days running from site to site and just seeing other tourists).

But I have a few questions... would it be better to get on a train directly from the airport and head to Florence, then work my way back through Tuscany to Rome, or go through Tuscany first, then Florence and return back to Rome. (It seems to me best to spend my last several days in Rome, so I don't stress out about getting back to the airport in time for my flight).

It seems like it might be difficult for me to explore Tuscany without renting a car - how difficult would it be for a person traveling alone, who's never been to the country to navigate through Tuscany? Have I lost my mind for considering it? (I definitely will ditch the car in Florence and Rome). Several years ago I drove across Ireland and was able to pre-plan my driving destinations easily enough and not get hopelessly lost (though I did have a friend with me on that trip).

Also, in Tuscany - for a single person, any recommendations about staying in a b&b vs agriturisimo? I'm looking at somewhat of a budget trip but not so budget as to stay in hostels (I'm in my mid-40's and know that a hostel would make me miserable). In Florence - better to look for an apartment in town or a b&b or agriturisimo just outside of Florence? In Rome - thinking of trying to find an apartment or room via airbnb - any thoughts on this? I rate equally on the scale of being an extrovert and an introvert, so I am fairly outgoing, friendly and easy to get along with, but I also like having some down time to myself as well.

I am so looking forward to this trip and really appreciate any advice! Thanks...

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