The sunset in Oia is definitely in the top 5 I’ve ever experienced. The caldera view is incredible, so adding a sunset to that is totally breathtaking. There is one downside though: the crowds. It’s seriously insane how many people come out to watch the sunset. October is not a popular time to visit Santorini, so I can’t even imagine how much worse it is during the high season.
One way to make it more enjoyable is to reserve a table at a restaurant with a sunset view. It’s definitely important to do this in advance. We ended up doing it the morning of and could only get a row 2 table. The view was still nice but definitely could have been better. It’s crazy how quick the crowds left after the sunset – no one stuck around in Oia at all. My sister and I headed back to Fira, where we were staying, at around 8. Fira is more where the nightlife of Santorini is. And I definitely recommend going out there!
For our sunset viewing evening in Oia, I wore my new pink off-the-shoulder dress (it’s under $15!!!!) with my wannabe Grecian tie-up sandals. I loved the light pink against the white & blue buildings and the gorgeous hot pink flowers that are everywhere in Santorini. It is so incredibly hot during the day (it totally feels hotter than the temperature!) and then it does cool down a lot at night. I was worried that I’d be cold once the sun went down, and I was. I would definitely recommend bringing a jacket if you go to Santorini in October!