‘Many refugees set up business here’: The secrets of Europe’s ‘friendliest’ city

At Tyrosyra, near the mountain village of Vissas, cheesemaker Giannis Perris said he couldn’t understand why Ermoupoli had only come second in the awards, behind the Brazilian city of Arraial d’Ajuda. “I bet no-one’s even heard of that other place,” he muttered, handing me a platter of barrel-aged frangosyriani cheese.

After a series of wrong turns led me to the traditional stone farmhouses of Kroussa village, and then to Katergaki’s rocky nudist beach, I made it to my final destination: Ousyra, an organic winery founded a decade ago by Edward Maitland-Makgill-Crichton, a Scot, and Eileen Botsford, his Greek-American artist wife. Heading out to the vineyards along a dusty path fringed with wild thyme, Edward told me that Ousyra, the original Phoenician name for Syros, means “happy place”. Perhaps the island’s friendliness is simply a case of nominative determinism. 

As we sat sipping wine, the setting sun turning the vineyards pink and the day’s furnace-like heat giving way to a cool evening breeze, I asked Edward what he made of Booking.com’s endorsement. “Of course Ermoupoli is the friendliest place on earth,” he grinned, offering me a refill. “It’s here on the happy island of Syros.”

How to do it

Fly from Heathrow to Athens (fares from £191 with Aegean; or Mykonos, and then catch a ferry (from £37; seajets.gr). Double rooms at the Castro hotel cost from £98 per night, including breakfast. Closer to the harbour, Skylight has double rooms including breakfast from £117 per night. Eat at Avant Garden (tasting menu from £41) and Mazi (mains from £12).