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Advice needed for Greece/Italy trip

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Hello there!

My friend and I will be travelling to Greece and Italy for the first time in September. Here is our itinerary:
Sept 10 - Sept 14th: Athens, Greece (Would love to find out what we can do in Athens or surrounding it)
Sept 15 - Sept 20th: Santorini (Suggestions welcomed!)
Sept 21- Sept 26th: Rome, Italy (Ciampino Airport)

We would like to know what we can do in mainland Greece for 5 days before we head to Santorini for a friend's wedding apart from the usual touristy visits in Athens. A little bad planning haha as we'd prefer to spend more time in Italy. Anyhow, any suggestions to explore greece is welcomed!

Please do recommend where we should go in Santorini as well (apart from the awesome views of the ocean!)

Lastly, we only have 6 days (SNIFF SNIFF) in Italy. Therefore, we would like to make the best out of it. Looking for beautiful scenic places to visit which are less touristy. We plan to rent a car and do a little road trippin starting from Rome. This is our road trip route:
Rome to Umbria (spend 2 nights in Rome and Umbria)
Umbria to Florence (1 night in Florence. We plan to roam Tuscany on bike and drink til we drop, haha)
Florence back to Rome on the 26th and Rome back to Athens. Will be spending a night in Athens again before we fly back to Malaysia.

Btw, how much is it to rent a car? Also is it safe and warm enough if we were to 'camp out' along our road trip? Are we actually allowed to do so? Would love to sleep beneath the stars and not get into trouble :D

Hope to gain some feedback!

Thanks in advance!
May

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