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Italy trip - pls give advise, suggestions, ideas, recommendations-

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Hi Friends,
I am planning a 14 days Italy trip with mum and brother flying from
India and I fly from London and meet them at 14th June at 2000 hours. My plan was to rent a car from the airport and drive to Naples (or nearby quiet place enroute, because I don't want to be driving too long and too late, want to reach before hotel or BnB close) straight away and spend the night there and 15th morning drive to Pompeii and herculeanum (sorry about the spellings,pardon me) and stay the night in Sorento, 16th morning day trip to Capri and am also thinking of driving to Amalfi after the day trip and stay overnight at Amalfi, 17th Morning planing to do Amalfi and by evening drive to Naples, drop the car and take the train to Rome. Before Rome plan, I would like to ask some suggestions on accomdations in different places mentioned above, is it a good idea to stay at different BnB because this is what I normally do when on roadtrips.
17th night rest in Rome
18th in Rome
19th in Rome
20th in Rome Untill evening and then take train to Florence.
20th night rest in Florence
I haven't really looked what sights I should be doing and for how many days in Florence but just a rough idea on my plan .
21st In Florence
22day trip to Siena(?)- sleep Florence
23rd -rent a car( it's more convenient to put our luggages in car when we do sights) in Florence, day trip to Pisa and Luca - and sleep in Luca(?)
24th morning drive to CT - sleep in CT
25th morning drive to vineyards in Tuscan hilltops and cianti region(?)- take eve or late train to Venice - sleep in Venice
26 and 27 in Venice
28 morning fly from Venice.
The question marks in brackets(?) suffixed to places is the plan I am unsure of if it's practically achievable. I need your suggestions on those please
I would appreciate if you can give me some suggestions in what to do and where to stay in Luca and Florence . Is it really worth it to do Siena, because I want to atleast see Tuscany country side an vineyards and the cianti region. Which would be an experience Siena or Cianti? Is it possible to fit them in here somewhere. Because I would prefer to drive, it should be flexible. But I am more confused with my plan from Florence onwards. I hope 2 nights should be sufficient in Venice. I know this sounds like fast paced and jam packed, but I am guessing it should be mostly OK as me an my brother could swap driving and take trains in major cities. So it's not driving continuously, although it would be his first time driving on the left side! I really welcome any and all of your suggestions to fine tune my plan. (Please pardon if I have done any spelling/grammar mistakes. It could be partly me and partly my phone auto correct option which is not correct most times)

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