My first time in Santorini, I arrived on a late-night flight and a taxi took me through pitch-black night to Perivolas Hotel. I had no idea the view that awaited morning, opening my door to that pool that hangs off the edge of Oia above the caldera. Recently its owners unveiled Perivolas Hideaway that’s a private villa retreat on the island of Therasia on the opposite side of the bay with full staff of 8 and private boat for exclusive back-and-forth use. Those that don’t need quite so much decadence, minimalist Oia Blue by Villas of Santorini is ideal for second-time visits with its cave houses detailed with private terraces and stylish kitchenettes along the caldera rim.
Much of Santorini has managed to develop without disrupting the charm of its individual villages. But during July and August, there are moments when English is the only language you hear and the island’s more popular corners are painfully touristy. Opt for morning or evening exploration of shops like Mamayoma Art in Oia or an afternoon sculpting lesson at Grigoris Kouskouris’s SPIRA gallery in Pyrgos. In-between, explore the historic Akrotiri or village of Emporio before heading to the beaches of Perivolos with their eateries like Τa Dichtia or Seaside by Notos and barefoot bars like Chilli.
While many visitors are underwhelmed by the simple food scene found on Santorini, standouts like Koukoumavlos and more-fashionable Selene are two of the best on the island. Those looking for more of a waterfront setting find Dimitri’s that has the best fish in Ammoudi or 1800 in Oia that is the toughest sunset dinner reservation on the island. Afterward, consider an outdoor movie at the Cine Kamari through summer or drinks at newly renovated Tango Bar designed by local Interior Design Laboratorium before 2am calltime at Enigma.
