Legendary Oia is the most famous and the most popular place on the whole island. This is the place that we see the most postcards from Santorini. It's truly amazing and charming!
However, due to tourist congestion, it's very hard to make any good pictures there and even to enjoy the sunset in a romantic atmosphere: during it, tourists literally sit on each other's heads! The locals are tired from this, plus the high number of tourists interferes with privacy in hotels. For this reason, more and more beautiful locations are closed for tourists.
For this reason unfortunately we can not recommend Oia for photoshoots. The only way to have a guaranteed good photo session there is to be a guest of some beautiful hotel in the area or a hotel which has a great view and ask them about a possibility of a shoot. Among our recommendations for it are the Katikies hotel and Aspaki by Art Maisons.