BACKSTORY: Built in the 18th and 19th centuries and renovated in 2009, this former captain’s house—part of the luxury boutique chain Yades Greek Historic Hotels—comprises 16 houses named for the island’s winds. The residences at the bottom, Skiron Houses, originally hosted the bishop and nuns who maintained Santorini’s cathedral, the postcard-worthy white bell tower of which is right next door.
ROOM WITH A VIEW: Like many traditional homes on Santorini, Aigialos is built into the side of the 980-foot caldera cliff, with buildings jumbled on top of one another. At the apex, you’ll find the sun-bleached Voreas House, which boasts stunning sea views.
WHAT YOU’LL FIND RIGHT OUTSIDE: The town of Fira, where the hotel is located, has a maze of rambling cliffside alleys that are great for strolling around. A short, madcap bus ride will take you to the town of Oia, which has lovely spots to watch the sunset. The island is also speckled with wineries, which are worth a tipsy day out.
HOT DISH: Famed Greek-American chef Marisa Churchill heads up the kitchen at Aigialos, which delivers dishes like crispy tomato keftedes and braised lamb shank to your terrace, so you don’t have to take your eyes off the view for even a second (watch out for the steak knives). Make sure to try the Assyrtiko wine, a mineral-y white made from local grapes.