Concierge.com's insider take:
Built in 1993, the family-run Anemomilos was one of the first boutique hotels in the Cyclades to appear somewhere other than Santorini or Mykonos, and it has continued to please. For one thing, its setting is spectacular: From atop a sea cliff, the 16 studios (each with an open-plan sleeping-living-kitchenette arrangement) all boast views only slightly less panoramic than those from the caldera of Santorini. (For the best views, opt for a blue-line apartment, or just hang out at the pool.) Additionally, the management is unusually progressive: They have long offered, for instance, a room designed with disabled guests in mind—something about as common in Greece as a nonsmoking section in a restaurant. The room decor is simple, pretty much the same traditional white with blue trim as the exterior, but it goes well with the simplicity of the island, which is just hard enough to get to that you won't be bothered much by the types of people who, if they do travel at all, should really spend their entire time on Santorini.
Closed October through March.