A mythical ancient island that endured one of the largest volcanic eruptions in history, Santorini feels like no other place on earth. Here, everything is brighter: the whitewashed cube-shaped houses, the lapis lazuli sea, and the sunsets that light up the caldera. Base yourself in picturesque Oia, on the island’s northern tip. It has the best views, particularly from the vertiginous terraces at the luxurious Katikies Hotel. If you prefer to trace the footsteps of countless fishermen from centuries past, opt for an unobstructed vista from one of the Spitia Houses, two traditional cave dwellings that Athens designer Panos Zaverdinos has updated with marble sinks, kitchenettes, and platform beds. From there, a staircase corkscrews 300 steps down to Amoudi Bay, where you can swim to the church of St. Nikolas Peramataris, on a black rock only 40 feet away. Back in Oia’s town center, locals congregate in the courtyard at Roka for tasty mezes—fried eggplant with tomato; apple and feta pie; fava purée—and glasses of assyrtiko, a dry white that’s bottled at neighboring Domaine Sigalas. You might even venture to the winery for a low-key tasting of its Vinsanto.