Winemaker Michael Kouloglou has named the off-season as the best time to visit Santorini, describing a period that runs from late September until around May. He moved to the island from the Athenian Riviera town of Piraeus 11 years ago and has since launched Orycton, a small-batch Assyrtiko made from old vines, which won at the 2023 Decanter World Wine Awards.
Kouloglou said Santorini has two distinct lives: the island experienced by millions of summer visitors, and another that begins in October and lasts until spring. He described autumn as bringing relief after harvest, winter as offering complete peace, and spring as filling the island with optimism before the new season.
According to Kouloglou, autumn still draws some travellers, but they tend to seek a quieter side of the island, walking, hiking and visiting wineries and small villages. By the end of November, he said, even the last seasonal workers have left, and Santorini belongs almost entirely to its locals.
He pointed to Karterados and Messaria as areas that become the island's hubs during the off-season, staying busy year-round as summer venues close. He also noted that many locals organise their year around Orthodox saint feast days, with each small chapel celebrating its patron saint through a panigyri, a traditional village festival.
On food, Kouloglou said he spends off-season time at Pentozali, a taverna serving meze from Santorini and Crete that becomes a gathering spot almost exclusively for locals. He named an omelette with wild asparagus as a seasonal dish when spring timing allows, alongside traditional Santorini fava topped with sautéed onions.