On his last leg – literally – of a summer tour, our writer finds two lesser-known Cyclades islands are full of mostly pleasant surprises, from the warm hospitality to swimming off deserted beaches

Dawn was breaking as I swam out from Paliochori beach. Twenty metres offshore, in the first rays of sunlight, I could see bubbles emerging from the sea bed. There was a roaring in my ears, like Poseidon’s kettle about to boil, plus some alarming gusts of warm water. Island of Milos, I thought, you are full of surprises: a volcanic Jacuzzi in the sea itself. Then I got out of the water and walked up the beach barefoot, straight into my second surprise: a thorn bush.

I yanked out every single one of the finger-long spines, but the last one broke off in my ankle. An hour later I couldn’t put my foot down. Was Milos having a joke? Anyone for island-hopping?

Milos was the fifth stop on my exploration of the lesser known Aegean islands, a journey that has revealed the wonderful diversity within those specks of land scattered between mainland Greece and Turkey. But Milos, I was fast realising, is different on a wholly different scale: starker, sharper and sometimes downright weird. There’s a beach only accessible by ladder, a taverna that stands in the sea and strange rock formations everywhere.

I was staying in a lovely hotel, Villa Notos, tucked into the cliffs on the outskirts of the port town of Adamanatas. My next few days were supposed to be spent hiking, but that prospect now seemed unlikely. Elena, the hotel owner, dug around in my ankle with a needle and declared the thorn too deep. I caught the bus up the mountain to the hospital where a stern-faced doctor spent 10 minutes exploring the interior of my ankle with a longer needle, then told me there was no thorn. I agreed: anything to escape his alarming ability to withstand pain, in other people. I could feel the thorn. I named it Odysseus and put a plaster on the livid red scar where he had entered the Trojan horse called Kevin.

Facebook Twitter Pinterest Clambering down the ladder to Tsigrado beach on Milos. Photograph: Kevin Rushby/The Guardian

Elena at the hotel was determined to find things I could do while hosting Odysseus. She called her friend Dimitrios, who had the keys to the caves under the hotel. I only had to hop down two flights of steps and there was Dimitrios next to a huge iron door that I hadn’t noticed before. We entered a long tunnel in the rock and walked into the mountain.

“In the second world war,” Dimitrios said, “the Germans occupied Milos because of its natural harbour. They tunnelled into here to create stores and a hospital.”

For years after the war the tunnels lay empty and unused, a warren of cool caverns, crying out for a purpose. Now Dimitrios and friends have started putting on art shows, which add surreal touches to some of the spaces.

I went up to see Elena. “Sit down on your terrace and we’ll bring you food.”

Facebook Twitter Pinterest In the tunnels below Adamanatas town, Milos Photograph: Kevin Rushby/The Guardian

Elena is Greek hospitality incarnate. Sit in front of her impressive desk overlooking the little beach below and before long coffee and cake will appear. Give it a little longer and some fascinating story will emerge, maybe about her great grandfather, who refused to surrender his pistols to the government and was named after his moustache – I’m summarising. Homemade cheese pie came on a tray with coffee. Later a bus timetable and map arrived, along with a message. I was to go to the costume and cultural museum up the mountain at Plaka.

The bus services on Milos are excellent. I rode up the hill, then limped through the labyrinthine lanes of Plaka. Down by the sea you might find “happy hour” bars and souvenir shops, but Plaka feels authentic: family houses, children’s toys in the alley, cats, a few good restaurants and bars. One of the houses has been turned into a museum. It’s a tiny place and you could easily miss it. There are no videos, no interactive exhibits, not even a demonstration of anything. Were it not for Odysseus, I would never have gone, and never met the custodian, Iro. “Elena Gaitanis sent you? Did you know her surname means ‘curly moustache’? Let me show you her great grandfather.”

His photo was on one wall: a piratical outlaw in giant pantaloons, pistols in his belt and that eponymous moustache. No wonder that when the island governor had demanded he surrender his pistols, Gaitanis had sent word: “Come and get them.” But nobody dared.

Facebook Twitter Pinterest Iro (left) with visitors in Plaka’s cultural museum. Elena’s great-grandfather is in the photo on the wall. Photograph: Kevin Rushby/The Guardian

With Iro as guide the museum was a revelation, a window into the former life of the island. She told me how every evening in Plaka would end with each housewife calling in her chickens by name, showed me the surprising dresses women wore for their wedding nights, explained how the priest got his daily bread, and so on and on. Each time I was about to leave, she yelled, “Stop! There’s one thing I must show you.”

Eventually I hobbled away and climbed steps to the top of the hill, the fort, where I enjoyed the magnificent view and took off my boots. The plaster was intact. Another bus ride took me back to sea level and the wonderful Klima, a series of colourful boathouses dug into the cliff. I swam and fell asleep on a bench. Next morning Elena enquired after my ankle. The plaster had survived one swim and two showers. Odysseus had gone quiet. I could walk again, and island hop too.

The last island on my adventure was Sifnos, a 50-minute ferry ride away. It loomed up on the horizon, looking massive and forbidding and far quieter than Milos. I stayed at Delfini, a friendly little hotel on the rocky coast within walking distance of the port. I took a rest day for the sake of my ankle and then set off at 5am on what I had decided would be my last and most ambitious yomp of the trip.

I climbed the vast mountainside opposite the hotel in semi-darkness, crossed a windy ridge and then took an ancient cliff path through crumbling antique terraces fragrant with juniper, thyme and sage. I drank from springs and explored abandoned villages. Lizards and partridges scattered before me. At midday I reached Vathy, a seaside village popular with French tourists.

Facebook Twitter Pinterest Kevin on the trail on Sifnos

After a swim I chose the simplest taverna and ordered revithada, chickpea stew, a Sifnos speciality. George, the owner’s son, talked proudly of the island’s culinary traditions. “When people have a cooking question in Greece, or they want a recipe, they say, ‘look in Tselementes’. It’s a book – the book. Tselementes has come to mean fine cooking. But Nikólaos Tselementes was a real person, a chef from Sifnos.” (He wrote an influential cooking series in 1910 called Odigos Mageirikis but his name has become a synonym for “cookbook.”)

George brought me caper salad, another Sifnos delicacy. Eventually I dragged myself away and continued walking, now in stunning heat, over a couple of hills and down to a deserted beach at Fikiada, where I collapsed in the shade after a swim.

Later, in golden evening light, I found some spectacularly ancient olive trees, hollowed-out giants that might have been saplings when Alexander the Great was alive. The oldest olive tree in Greece is said to be more than 3,000 years old.

Facebook Twitter Pinterest George and his mum, owners of Taverna Symposio at Vathy on Sifnos. Photograph: Kevin Rushby/The Guardian

I walked on and on until dark, then caught the last bus home. My Greek walking epic was finished.

It had been a wonderful and inspiring journey. Behind its success lay a comprehensive and reliable ferry system (it never failed me), and a dependably hospitable roster of small family-run hotels. I never ate fancy or expensive food, often happy with pies from the bakery or a salad. It was the simple things I enjoyed most: the morning light, the sun-blessed tomatoes, the antique cobbled paths, the cool swims, the falcons playing with the wind.

Every morning at dawn I pulled on my boots, eager to get outside and see what the day would bring. And they all brought sheer pleasure.

Except, of course, for Odysseus. That accursed wanderer came back to England with me, hiding under the miraculously tenacious plaster. And then, when I first got in a car to drive, as if in horror at the end of my glorious summer of walking, he protested. I reached down, ripped that plaster off, and there, stuck to the surface, was a grisly black thorn, a centimetre long. Odysseus had made his point: my island-hopping was over – for now.

• Accommodation was provided by Inntravel, whose three-centre, ten-night, self-guided Enchanting Cyclades walking tour starts at £915pp, including B&B, notes and maps, transfers between ports and hotels and an internal flight Milos to Athens. Book ferries at ferries.gr; Folegandros to Milos €39.80, Milos to Sifnos €15, Sifnos to Piraeus €50. Accommodation in Athens was provided by The Foundry Suites (apartments for two from £102)

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