Cruising close to the clouds on the island’s loftiest locale, Santorini Sky is a series of villas set away from the sunset-chasing hordes of Oia. There are three sites, each of which is in the southern part of the croissant-shaped coastline, near the ruins of Akrotiri, the beach clubs of Perivolos and all the fun of Fira. They are: Pyrgos, the mountainside Elias and the even-more-stranded Diapla. At 2,000 feet above sea level, the views keep on coming. Each villa has its own pool, along with a kitchen or kitchenette – helpful since, with a setting this good, you’re probably not going to venture far.