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.
Santorini Affordable Tip: Catch a poetry reading—with free wine and snacks—on the outdoor terrace at Atlantis Books, an independent shop owned by a group of hyper-literate expats. It hosts events throughout the year, including a Super 8 film festival and the Caldera Literary Festival in October.
Santorini Active Tip: Charter a crewed catamaran from Santorini Sailing Blue Lagoon Cruises to visit the still-active volcano on Nea Kameni, about two miles away from Oia, where you can hike, snorkel, and float in the caldera. 30-22860/21380; half-day charters from $1,075 for up to six people.
Santorini, Greece: World’s Best Scorecard
No. 1 island overall
No. 1 island in Europe
Katikies Hotel 93.07