Downtown Luxury Slum

I can’t claim to be the best at planning a trip to Santorini. We visited for 2 full days and 3 nights and stayed in the most beautiful Airbnb in the middle of nowhere on a cliff overlooking the ocean. We rented a small car to drive around the island because it was too windy to do the boat tour we had planned – don’t rent an automatic on Santorini if you can drive manual. And we did a wine tour that was fun, but if you stay in Thira / Thera / Fira, you could probably plan your own wine tour just as well.

That said, we did find the absolute best place to watch the sunset in Oia. I read tons of recommendations before we went and basically everyone said to go to Oia Castle aside from one person who said to skip Oia altogether and watch from Imerovigli.

Here’s the view from Oia Castle around sunset.

So we pushed our way through the crowds around Oia Castle and found a spot to set up camp about 30 minutes before sunset. There were only a half dozen people blocking our view. My travel companions wandered off to get some refreshments while I attempted to hold down the fort. While getting refreshments, one of my travel companions made an offhand comment to the store clerk about how packed in everyone is and the clerk responded by saying, “I don’t know why the do that when you can walk down two more windmills and get great views with no crowds.” So two of us wandered down to see if she knew what she was talking about. She did.

The Best Sunset Views on Santorini

Right here, is where we watched from. It was literally the best but it was also just a vacant lot with a nice wall to sit on. So if you wanted something a little more luxurious, you could book a night at The Sunset Windmill, Canava View House, or The Sunset Windmill or make dinner reservations at Elinikon Oia Restaurant, all of which will have essentially the same views but better seating.