Greece - Cyclades

Category: Mediterranean East,

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The Greek islands are the quintessential cruising grounds for yachts. Perpetually associated with such legendary luminaries as Stavros Niarchos and Aristotle Onassis, Greece’s links between shipping and yachting have focussed the nation on maritime pursuits, creating an unparalleled playground for yachtsmen.

For a nation largely composed of islands, distances between the main centres can be deceptive but, particularly in the summer, communications between Athens and the islands is so inexpensive and frequent that embarking in Piraeus and finishing in an island is not only practical but allows some truly off-the beaten track places to be explored.

Our sample itinerary, prepared with one of our charming owners, takes in fifty year's local knowledge of sailing the islands and discovers some very special places known only to him and his family.


Day 1

Piraeus port is one of those maritime rarities – a working blend of commercial and pleasure shipping with a constant bustle of ferries leaving for the islands, commercial vessels discharging cargo and a thriving yacht and shipbuilding community. A first taste of the professionalism of the Greeks is the sight of the experienced captain navigating through the hustle and bustle of this busy port en route for Aegina and Poros where the guests have a chance to wash off the pressures of the city with a swim in the island’s clear blue waters. A late afternoon steam takes her to Hydra for a peaceful overnight anchorage.

Day 2

After an early morning stroll around the 18thC Hydra town with the chef to collect freshly baked bread, the yacht sails for Milos a mix of magnificent beaches, hot springs, white cube villages perched on multicoloured cliffs, churches, volcanic relics and weird rock formations. None is more surprising than the extraordinary Bandit’s Lair of Kleftiko, a series of caves large enough to conceal pirate ships. Swimming, snorkelling and exploring the magnificent rock formation passes a delightful afternoon before weighing anchor to sail round to Port Adamas, a delightful mix of unspoiled Greek village and sophisticated nightlife.

Day 3

Late morning finds the yacht to the north east of Milos at Poliegos, so named for the multitude of goats – and zero population - inhabiting this tiny undiscovered islet. Good swimming precedes a leisurely lunch anchored off the rocky shore before upping anchor for Folegandros, an unspoiled Cycladic island that has been called "an untouched piece of true Greece" and those who come to the island looking for organized water-sports, discos and wild nightlife will be disappointed. But a lack of nightlife does not mean a lack of good restaurants and cafes in the charming car-free capital Hora, three kilometres from the sleepy port of Karavostassis.

Day 4

A short sail to the east lies Sikinos, still one of the most untouched islands of the Cyclades. The quintessence of peacefulness, its island character adds to the attraction for those in search of authentic Greece. Going ashore for a walk requires packing a camera – the scenery is beautiful. After lunch the next stop is the amazing caldera of Santorini. The island, officially named Thira, was destroyed by a massive eruption in 1500BC leaving just the edges of the flooded volcanic crater and forming perhaps the most spectacular anchorage in the world. Sunset over the islet of Thirassia is a sight not to be s missed and the captain will know where to take full advantage of the stunning location.

Day 5

A morning passage to Ios, the original hippy island of Greece; it has a reputation for hedonism and a party scene but the destination today is some isolated and beautiful coves to the north and west with some of the best beaches in Greece for swimming, well away from the brashness of the town. Sailing onwards, the islands of Koufonisi and Shinousa could not be a greater contrast to the reputation of Ios. Crescents of sand alternate with wild-looking caves that the tide has carved in the rocks. For sheer peace and tranquillity, the anchorage for tonight takes a fair degree of beating.

Day 6

The yacht heads to Shinousa for a morning swim and breakfast before turning north for Naxos. The largest and most fertile of the Cyclades, Naxos’ abrupt south coast gives over to sheltered coves and sandy beaches on the west. The capital Hora is one of the most attractive towns in Greece and while the yacht is being refuelled it is worth the climb past old stone houses lining the winding lanes to the magnificent Venetian castle high above the port. The island of Paros is the destination for tonight and its second town, Naousa, lies to the north of the island in a pretty sheltered bay.

Day 7

The yacht steams due north for Delos, one of the most important sacred sites in Greece. Birthplace of Artemis and Apollo, it ranks second only to Delphi in mythological importance. As well as enjoying the beautiful waters. It is worth exploring the several historical sites dotted around Delos where remains of the many temples that proliferated across the island are still being excavated. One of the great joys is that the last boat back to Mykonos departs at 3pm leaving the island peaceful and a delight to explore. There is no habitation on Delos so the island becomes almost a private fiefdom when the tourists have left. As the sun sets, the captain heads across the one mile strait to Mykonos for the night.

Day 8

Awaking at anchor off Mykonos may be a rude shock after sampling the abundant nightlife for which the island is famous but the international airport is close by and a transfer has been arranged for those returning to Athens.

To enquire about this destination or to discuss creating your bespoke dream holiday, please get in touch.

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