A whitewashed Cycladic village above an indigo Aegean bay at sunset

The Cyclades

Ten days of real sailing between white islands, from Athens down the chain to Milos.

10Days
≈210Nautical miles
AthensEmbark
MilosDisembark
May to SeptSeason
Day1
Vourkari, Kea

Athens to Kea

Clear the Attic coast by early afternoon and make the short crossing to Kea, the first white island in the chain. Vourkari's harbour front is three tavernas and a chandlery, which is all a first evening needs.

Day2
Ermoupoli, Syros

South to Syros

A proper morning sail with the meltemi on the beam. Ermoupoli, the Cyclades' forgotten capital, rises in neoclassical tiers of ochre and rose: an opera house, marble squares, and not a souvenir shop in sight.

Day3
Ornos Bay, Mykonos

Mykonos, on your terms

Anchor away from the noise in Ornos and take Mykonos as a raid: morning in the old town while it still belongs to its cats, lunch back on board, and an afternoon at a quiet beach the tender knows on the north shore.

Day4
Naoussa, Paros

Delos and on to Paros

An hour on the silent marble of Delos before the tour boats, walking streets abandoned two thousand years ago. Then a broad reach south to Naoussa, whose miniature Venetian harbour hosts the best table in the islands.

A whitewashed Cycladic alley with magenta bougainvillea
Day5
Naxos town

Naxos, the green island

The tallest, greenest Cyclade. Climb through the Portara at sunset, or drive inland to marble villages where the kafeneion has one table and it is yours. The chef restocks here: Naxos cheese, potatoes, citron.

Day6
Koufonisia

The Small Cyclades

Down among the islets: Koufonisia, where the water turns a blue that looks retouched and is not. Swim into sea caves, lunch on the hook, and let the afternoon disappear without appointments.

Day7
Manganari Bay, Ios

Ios beyond the reputation

Ios keeps its south coast quiet. Manganari's triple bay is sand, salt cedar and one grill house. An evening climb to the chora rewards with the archipelago laid out in lights below.

Day8
Below Oia

Santorini from the water

Approach the caldera as it should be approached: by sea, cliffs of ash and pumice rising a thousand feet overhead. Anchor beneath Oia, ride up before sunset, and watch the crowds face the wrong way while your boat swings quietly below.

A Greek harbourside taverna at dusk, tables at the water's edge
Day9
Karavostasis, Folegandros

Folegandros

The connoisseur's island. A cliff-edge chora, one bus, and a bay where yours may be the only mast. Dinner in the square under the almond trees, where the waiter remembers our crews by name.

Day10
Adamas, Milos

Milos and farewell

A final morning among Milos' mineral coves, white as bone at Sarakiniko, then into Adamas to disembark. Flights connect through Athens; regret is universal.

Make it yours

Ten days is the honest minimum for the Cyclades; with the meltemi blowing, the crew will re-order islands so the wind works for you, never against. Twelve days lets you add Sifnos and Serifos on the way home.

Sail the wind's own islands

May and September give the kindest wind and the emptiest harbours. Tell us your dates.