Cyclades Cruising Guide

The birthplace of democracy, Athens boasts three millennia of magnificent history. Famous philosophers Aristotle, Plato and Socrates debated their way along these ancient city streets. Today the city is flush with iconic ancient ruins, including the world-famous Parthenon.

But it’s not just history buffs who revel in the Greek capital, Epicureans are in for a treat too. Wander through the colourful spice stalls and fishmongers within the Varvakios Agora (Athens’ Central Market), or head to Spondi, Greece’s top restaurant and wine cellar for over a decade. This double Michelin-starred spot serves contemporary dishes like sea urchin, shaved fennel and citrus yuzu.

For a combination of antiquity and tranquillity, set sail for Kea. Its verdant interior is so historic that 130 churches lie scattered amid olive groves and almond trees.

Scuba diving is banned in several areas for good reason: you’re as likely to come face-to-face with an Ancient Greek artefact as you are a rainbow wrasse, but grab a mask and snorkel and head for Megales beach. This romantic sliver of sand has a millennia-old dock submerged beneath the surface. On isolated Spathia beach you'll be lucky to find a phone signal, let alone a parasol.

Ilouida, a recumbent stone lion, is Kea’s Instagram moment. This supine statue has been gazing over the sleepy shoreline since 500AD.

Prosperous, elegant and green, Syros differs starkly from its Cycladic neighbours. In the 19th century its capital, Ermoupoli, was one of the wealthiest ports in all of Greece, as its handsome harbour attests.

Sandy beaches abound at palm-lined Galissas on the southwest coast. Nearby, the summer sea at the fishing village of Finikas is utterly transparent and as warm as a bath. It’s here that guests will find the spellbinding church of Agios Stefanos, which lies hidden in a watery sea cave. A little further north, Kinio is an even smaller fishing haven, with a magnificent curve of sandy shore.

Sifnos’s main village, Apollonia, sits in the centre of the island on high. Here, three pretty hamlets have merged into a medley of white-painted homes, connected by little piazzas filled with cafés. Dining on Sifnos is an authentic experience. Visitors will find some of the Aegean's best old-style Mezedopoleio spots serving island classics like kleftiko (slow-cooked lamb wrapped in paper) and giouvetsi (veal casserole). Go greek with a glass of aniseed-flavoured ouzo.

Ios is renowned as a white-hot party island, where Caipiroskas and manhattans keep the clubs rocking until dawn. Daytime recovery is spent on sandy south-facing Milopotamos beach, as chic as anywhere on the

Riviera in summer. The main village of Chora is a tranquil Cycladic vision of whitewashed cubist cottages, but as the sun sets over the main piazza, the town wakes up and dons its dancing shoes. Tranquility is within easy reach for those with their own boat. The beachy bay at Ormos Manganaro is far easier to access by sea than by land. Lucky voyagers will find less-visited stretches of sand at spots like Psathi, Agia Theodoti and Kalamos on the west coast.

Not for nothing was Santorini known to the ancients as Kallisti, or ‘most beautiful’. Sailing into the island’s deep blue-flooded caldera is the high point of any Aegean voyage. For maximum effect, try to arrive around sunset, when the high cliffs that rim the crater glow red, pink and ochre.

Santorini’s bizarre landscapes are the result of a mega volcanic eruption in 1470BC. Another loud bang in the 18th century created the islet of Nea Kameni, where visitors can bathe in bubbling water heated by the still-active volcano. Black sand beaches sweep around Santorini’s east coast. The inner rim of the crater is more protected, and houses a necklace of pretty traditional villages with a fine seafood taverna apiece.

In the deep blue of Kalotaritissa bay, large groupers lurk in deep crevices behind anemone-covered boulders. Fish swim in kaleidoscopic shoals, and there’s a good chance of spotting an octopus too. Superyachts sail back in time on Amorgos. The island clings to age-old traditions of music, dance and greek island cuisine. You may be invited to take part in a celebratory circle-dance at a village festival, or to sample local delights such as bright-orange sea slugs, purple fousta shellfish, lemon liqueur or wild artichokes.

Naxos is favoured by a handful of cognoscenti who return year-on-year. But its soft sands, vineyards and olive groves remain blissfully undisturbed. The island’s best beaches are just south of town, and what beaches they are. Long stretches of sand and crystal-clear shallows dominate the coast between the three small resorts of Agios Prokopios, Agia Anna and Plaka. The dramatic scenery and pebbly beaches of the near-uninhabited east coast offer the ultimate superyacht lure; secret bays and tiny coves line either side of the peninsula, only reachable by boat.

With its whitewashed villages and some of the finest sandy beaches in the Cyclades, Paros is a picture of tranquil charm. Its little capital, Parikia, is a colourful fishing port. The town’s long sweeping waterfront dissolves into a labyrinth of whitewashed houses and flower-filled lanes.

Superyacht guests can thank their lucky stars, as Paros’ coastal gems all lie a short steam away. A dozen tiny uninhabited islands stud the deep blue bay. For the best beaches, sail over to Paros’ little neighbour, Antiparos, which has just one little harbour village at Chora. Its uncrowded ribbon of fine sand at Agios Georgios is worth a Skype call home.

Serene Tinos could hardly be more different from its indulgent neighbours. This tranquil isle is the perfect antidote for anyone who has over-partied on Mykonos or over-eaten on Delos.
With no airport on the island, its beaches are as tranquil as can be. The pebbly bays of Rochari, Malli, and Ormos Panormos melt into a deep greek blue and are most easily reached not by land, but by sea. Inland, cobbled mule paths zigzag between tiny villages. Distinctive local dishes abound on this isolated island and include wild rabbit in wine sauce, Tinos’ famed smoked siglino pork and the island’s Tiniako cheese.

Mykonos is the arguably the most photogenic island in Greece. Since the 1960s hedonist Hellenophiles have descended on its white sugar-cube houses and beaches of silver sand. The labyrinth of Mikri Venetia – or ‘Little Venice’ – has formed the backdrop for countless fashion shoots. Quite naturally, Mykonos is home to Greece’s only branch of Nobu.

The climax of any visit to Mykonos is the sail to nearby Delos. One of the ancient world’s most sacred islands, weathered stone lions stand guard over ruined temples and eerie sanctuaries. Three lovely bays on the uninhabited island of Rinia offer fine anchorages and excellent swimming. Snorkellers will find shoals of silver bream and rainbow wrasse for company.