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Italy/France Late September 2021? Any Suggestions?

We're getting married at the end of September and have finally decided on a trip! After some discussions we realized we wanted to have a relaxing trip with a mix of beach visits, city tours and visits to wineries.

We're thinking to fly into Venice, rent a car and travel south Florence, Rome, Naples, Amalfi Coast and then to Bari.

From Bari take a short flight to Marseilles and then a train ride to Paris with a flight back to NY.

Questions:

Recs on where to stay?

Where and who to rent a car?
Is that too many stops?

Has anyone taken the train through Italy? Is that a realistic option?

Any advice or tips would be greatly appreciated! Thanks for reading!

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Source: reditt

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