"Almost every building overlooking Santorini’s sunken caldera has been converted into a luxury hotel. I’ve stayed at dozens of them, but surprisingly few live up to those famous views. The Vasilicos is a cut above the crowded competition for several reasons. All seven suites are spacious and secluded, their terraces cascading down the hillside with wide-open views of the infinite blue. Even when the island seems to be sinking under the weight of its popularity, serenity reigns at this former summerhouse. Designed for sun-drenched gatherings with family and friends, it was built in the 1980s by Vassilis Valambous, a Greek art collector and bon viveur, from a cluster of collapsed yposkafa—the island’s unique cave houses. The atmosphere still has the warmth, intimacy, and personality of a home. From the capsule library (curated by legendary local shop Atlantis Books) to the custom-made beach towels, every thoughtful detail bears the personal touch of the elegantly understated owner, Daphne Valambous. Her brother Yannis has transformed the vineyards he inherited from their father into Vassaltis, one of the most exciting wineries on Santorini. If I’m traveling solo, I like to pop a bottle of its sparkling pet nat to toast the sunset, an almost otherworldly experience that is never the same twice (the wines can also be paired with a personalized tasting menu at the sublime two-table restaurant). Open since 2015, The Vasilicos is already a timeless classic. Like most loyal guests, I’d almost prefer to keep this very private hideaway hush-hush. Doubles from $420. —Rachel Howard" - CNT Editors