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Post-Greece Tour to Santorini

Our Rick Steves tour ends on 9/25/26, we plan to go to Santorini for 3 or 4 nights. We have a return flight in the afternoon of 9/29/26 to the US. I have few questions if someone would share their thoughts:

1) Should we stay at Santorini for 4 nights and return to Athens in the morning of 9/29/26 to fly out? Since this is the first time we are in Greece, we don't know if the flight from Santorini to Athens is reliable to take a risk. If not, we will just stay 3 nights and come back to Athens on 9/28/26.
2) Is it better to rent a car in Santorini or hire a taxi?
3) Which city (Fira, Imerovigli or Oia) shall we stay at?
4) Any recommendations on hotels?

Thank you for your opinion in advance!

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I can recommend Lithies Traditional Homes which is located in Firostefani. Our stay there was fabulous! IMO there are way too many variables to say if a flight is "reliable". The night before a flight home, we always choose to stay in a hotel located in the departure city.