Greece has over 200 inhabited islands. Tourism concentrates on roughly six of them. That gap between supply and demand is where the best trips are hiding.
Milos, volcanic, strange, and barely discovered
Milos is a volcanic island in the southwest Cyclades shaped like a crescent around a collapsed caldera. Its coastline has more beach variety than almost anywhere in the Mediterranean, from pale pink rock at Sarakiniko to sea caves at Kleftiko you reach only by boat, and the famous fishing village of Klima where the boathouses are painted in orange and teal and families have lived in the same cliff-face homes for generations. The Venus de Milo was found here in 1820. The Louvre took the statue; Milos kept the catacombs.
Naxos, the island that feeds the Cyclades
Naxos is the largest island in the Cyclades and the most self-sufficient. It does not need tourism the way its neighbors do, which shows. The interior is a different country: marble villages at 600 meters, ox carts on mountain roads, and kitron liqueur made from the leaves of a citrus tree that grows nowhere else. The Portara, a massive marble doorway standing alone above the port, was the entrance to an unfinished temple to Apollo in 530 BCE. You can walk up and stand inside it at sunset for free.
Folegandros, Santorini without the crowds or the price
Folegandros is a two-hour ferry from Santorini and receives a fraction of its visitors. It has the same Cycladic architecture of blinding white cubes, blue domes and jasmine-scented alleyways, but a Chora so perfectly preserved it is hard to believe it is still lived in rather than a film set. The Church of Panagia sits on a headland above the sea, reached by a steep cobbled path, and on Sunday mornings the bells carry across the whole valley.
Symi, the colorful harbor the cruise ships cannot quite ruin
Symi sits near Rhodes in the Dodecanese and its harbor, Gialos, is one of the most photographed in Greece: tiered neoclassical mansions in ochre, terracotta, and cream climbing a steep hillside above bobbing fishing boats. Day-trippers arrive from Rhodes in the morning and leave by 3 p.m. If you stay the night, you inherit the island. It is that simple.
When to go, and a word about ferries
May and late September are the best months for island-hopping. July and August are brutally hot and the ferries are full weeks in advance. The Greek ferry system is reliable but not obvious to newcomers, so book Hellenic Seaways or SeaJets tickets at least two weeks ahead in summer. A missed ferry on a small island is not a minor inconvenience; the next one might be tomorrow.
