Hello kind and experienced folks, I am thinking of dropping either Siena or CinqueTerre from this draft itinerary? What your thoughts?
Italy Itinerary DRAFT (Sep 6–20, or Sep 21 2025)
Flow: Sep 5 Chicago → Sep 6 Florence → Pienza Val d’Orcia → Chianti → Siena ? → Florence → Cinque Terre ? → Naples Herculaneum → Salerno → Pompeii → OR Pompeii → Salerno → Paestum → Rome → Fly home Chicago
We plan to have a car for Florence → Pienza Val d’Orcia → Chianti → Siena → Florence and then do the rest by train.
The detour to Cinque Terre takes time away from visiting Rome so not sure whether to drop it or how to modify the itinerary. I have never been to either Cinque Terre or Siena. I have been to Naples before and I am ok with a day there for food, views, and the Arqueological Museum and as a base for Herculaneum, spending the night at B&B Orsini64 and then on to Pompeii the next day with a night in Naples or Salerno.
We can add a day to this to return home on Sunday Sep 21.
My husband has never been to Italy.
We do plan to return to Italy (Milan area) so perhaps we could leave Cinque Terre for a next trip?
Thanks in advance for your suggestions!
I’m getting there! Phew!