Advice on travel plans- Bellagio- Santa Margherita Ligure -Tuscany Chianti


New member
My family of 4 will be traveling to Italy in July and I am wondering if I should rent a car for the entire trip or would it be easier to use trains. We plan on flying in and out of Milan and would love to see a few different areas.
Previous trip we did, Venice, Rome, Amalfi Coast. Below is my wishful thinking itinerary, I am flexible to take a day off the coast and not see Cinque Terre since we have been to Positano before. I also considered not going to the coast at all but my son really loves the water and boats. Please feel free to give suggestions I am really wanting to book my plans asap.

July 8th..arrive Milan early-either rent car or hire private car to take us to Bellagio
10th..Bellagio-day trip to Varenna
11th..head to Santa Margherita Ligure (train or rented car?)
12th..Santa Margherita-day trip PortoFino
13th..possible day trip to Cinque terre or just relax in SM
14th..head to Tuscany (is it easy to drive from the coast to chianti area? We would like to stay on a vineyard)
15th..Chianti-tour local towns
17th..head back to Milan stay overnight near airport (drive rented car or train?)
18th..Fly home from Milan

Thanks in advance so much!!