Artists and poets have long sought sanctuary on Hydra’s rocky shores. Leonard Cohen wrote “So Long, Marianne” in a house above the harbour while The Beatles holidayed in blissful anonymity. Cobbled lanes wind past stone mansions, art galleries and sun-dappled courtyards. Hike coastal trails to discover secluded swimming spots, then dine harbourside at Piato, a family-run taverna where the walls are lined with hand-painted plates by guests, including Kate Moss and Vivienne Westwood. For elevated dining with a view, book a table at Omilos, perched above the water and offering views over the bay and Jeff Koons’ celestial Apollo sculpture. 

Your next stop is Milos, a volcanic island sculpted by wind and tide. Its surreal landscapes are a photographer’s dream. At Sarakiniko beach, waves crash against bone-white rock formations resembling lunar dunes. Snorkel among rainbow wrasse, damselfish and shy octopus at Kleftiko beach, accessible only by boat, featuring soaring cliffs and emerald sea caves. When you’re ready to trade sea for stone, visit the ancient theatre of Milos, carved into the hillside with views across the bay or climb to the Church of the Holy Trinity for a moment of calm.  

Mykonos is where cosmopolitan glamour meets Cycladic tradition. Visit the iconic Kato Mili windmills, once powered by the island’s restless sea winds, to grind grain before meandering through the bougainvillaea-draped lanes of Matogianni Street lined with chic boutiques. The Church of Panagia Paraportiani is one of the most photographed buildings in Greece, and it's an iconic holiday snap there before heading to Interni, a garden restaurant where candlelit tables and creative Mediterranean cuisine make for a perfect evening. Follow the music to Scorpios or Cavo Paradiso, where the sea glimmers below the dance floor.

A short sail away lies Santorini. Hike the caldera’s edge from Fira to Oia, a trail lined with whitewashed chapels and their famous blue domes. Every turn reveals another picture-perfect view. Dive into the island’s ancient history at Akrotiri, a Minoan city preserved in volcanic ash, offering eerie echoes of Pompeii, or take a boat to Nea Kameni to walk across volcanic rock and bathe in sulphuric hot springs. 

Your final stop is the ancient island of Delos. With no permanent residents and an aura of quiet reverence, Delos feels suspended in time. Said to be the birthplace of the Greek twin gods Apollo and Artemis, Delos was once a sacred and powerful religious centre. Today, it’s a hauntingly beautiful open-air museum. Walk among the Terrace of the Lions, temples and mosaic-covered villas where ancient festivals once took place. 

And if you want to book a few nights on shore to give your sea legs a break, explore our selection of hotels across the Greek islands, such as the chic Nous Hotel Santorini, inspired by the rugged volcanic landscape, or the delightful Kalesma Mykonos, a family-owned luxury boutique hotel overlooking Ornos Bay. You can find all of these hotels and more on ASMALLWORLD Collection.