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October—Santorini, Greece

Published: Jun 27, 2017
Greece, Cyclades Islands, Santorini (Thira), Oia, village with view on sea
Restaurant overlooking the water in Santorini, Greece.
Jon Arnold—AWL Images RM/Getty Images

Cost to Spend a Week for Two: $6,115

Skip the tourist crush of summer and visit Santorini during fall to see its whitewashed houses stacked along the Aegean sea.For classic panoramic views, try staying at La Perla Villas, located in the village of Oia on Santorini's northern end. Also worth a visit is Fira, the island’s busy capital, which features bustling bars and restaurants along with narrow streets that wind along the edge of the island's caldera. Booking.com recommends spending the night at Lilium Santorini Villa, if you want to stay in the capital.