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French Riviera and Italy 3 weeks - need itinerary help and suggestions

Hi, we are planning a 3-week vacation to French Riviera and Italy. Have never been before (except for 1 day in Venice) and would like suggestions regarding proposed itinerary please:
Fri., Oct. 11 - Depart Toronto and fly to Nice, no direct flights unfortunately
Sat., Oct. 12 -Arrive Nice, train to Antibes – stay 5 nights, rent car and explore Riviera
Thurs., Oct. 17 – Train to Monterosso, stay 2 nights
Sat., Oct. 19 – Train to Florence, stay 4 nights, rent car, explore countryside incl. Siena
Wed., Oct. 23 – Train to Rome, stay 4 nights
Sun., Oct. 27 – Train to Naples/Sorrento, stay Sorrento 5 nights (Pompeii, Capri, Positano)
Fri., Nov. 1 – Boat to Naples, stay Naples near airport 1 night
Sat., Nov. 2 – Depart early morning Naples to Toronto, no direct flights unfortunately

1. Would you suggest a more efficient order in which to see everything? Or reverse the order?
2. Is there any possible way to fit Venice into this itinerary? Would love to if we can.
3. The most challenging to figure out is how to get from Antibes to Monterosso by train. It looks like we would go from Antibes-Nice-Ventimiglia (border)-Genoa-Levanto-La Spezia? So confusing! Can we stop at Pisa on our way or should we drive or train there from Florence?
4. Or skip CT altogether? Many have mentioned to visit either CT or Amalfi because they are similar, but they seem quite different from what I have read.
5. We love markets and cooking so would like to stay in an apartment in either Riviera or Sorrento so we can cook fresh produce ourselves (and save some money). Suggestions? Is that viable if relying on public transit?

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