I'd appreciate some help with planning my upcoming trip to Italy in the second half of July 2026, flying into Rome and flying out of Venice. The 14 days does not include the flight days. My wife and I will be travelling with another couple (all in our 40s). 3 of us have been to Italy before and 1 is very easy-going, so we aren't planning to do much in-depth visiting of the main attractions. The main goal for this trip is more towards activities/experiences, have good food and walk around the cities enjoying the vibes and shopping.
Given that, we were thinking of around 3 days in each place, except for Venice with 2 nights. From Rome, we would take the train down to Naples and then Sorrento, which will be our home base to make day trips to the Amalfi Coast. After 3 nights there, we plan to take the train back to Rome and get a rental car to drive up to the Tuscan countryside. We would most probably be staying in the Val d'Orcia region. We'd then drop off the car at Florence, spend 3 nights there and head to Venice by train.
The dilemma was whether to stay in Rome and then head down, or head down straight to Sorrento and then continue our trip up north. We decided that with the flight to Rome taking 17 hours in total, it'd be better to stay in Rome first and then head down. How does this itinerary sound? Is there any other place like Orvieto, or Chiusi that you would recommend getting the rental car from? Thank you!
PS : Flights have been booked but accommodations have not.