The Bliss List: Santorini, Greece
The Traditional Cave Houses at Alexander's Boutique Hotel of Oia—think white walls, cliff-side terraces, and gorgeous sea views—sleep from two to five and still have room for extra beds. Even better, you couldn't ask for a more charming and informed host than the owner, Alexander Bourtzoglou (011-30/22860-71818, alexandershotel.com, Cave House from $139).
At Vanilia restaurant, an 1872 converted windmill in the postcard-perfect village of Firostefani, dishes such as kotopoulo stin gastra, chicken with smoked Santorini tomatoes and sweet onion balsamic vinegar sauce, almost rival the scenery (011-30/22860-25631, vanilia.gr, chicken $23).
It's worth arriving early at Franco's Bar. You can secure a cluster of deck chairs and sip a round of Maria Callas champagne cocktails until it's time for the evening's main event: the sun slipping into the sea, timed to classical music (011-30/22860-24428, francos.gr, Callas cocktail $17).
Art Space Argyros Canava is a winery that doubles as a gallery, selling local paintings alongside its vintages (011-30/22860-32774). Krinos Art & Accessories stocks Sofia Balanou's handcrafted pillows painted with whimsical fish designs inspired by Santorini itself (011-30/69467-23374).
On the island's southeastern coast is Perivolos, a restaurant-lined black-sand beach ideal for people-watching and sunbathing. To get a taste of life as a local, visit the bustling village of Emporio.