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Help with Itinerary, choosing Florence and Venice over Chianti area

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So our tickets to Rome are finally booked. I have to book hotels / B&Bs in this week. so please help with this itinerary-

Fly into Rome on 29 May by 1 pm
Train to Florence, get a feel of the city
Explore Florence on 30th and 31st
(Question 1: is taking a wine tour to chianti area on one day and just spending one full day in Florence too rushed? Would you chuck the wine tour and just explore Florence for 2 days?)
Train to Venice on 1st
Explore Venice on 1st evening
Trip to Burano on 2nd
More of Venice on 3rd
Train to Naples on 4th, then ferry or private taxi to positano or amalfi
Explore AC on 4, 5, 6,7
Journey to Rome on 8th
(Q2: we are travelling with our 4 yr old daughter, so is a trip to Pompeii on the way back from AC to Rome too hectic? We can do a day trip to Pompeii on 8th instead or just not do it)
Reach Rome on 8th night or 9th morning depending on Pompeii trip
Spend 9, 10, 11 in Rome
Early morning flight on 12th back home

The alternative to this which had been thought of was to rent a car and explore chianti region, after 2 days in Florence. Stay at a wine estate on 1,2,3 and not do Venice at all. Then move to amalfi and Rome.

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