Sailing the Cyclades: A Seven-Day Route Through the Heart of the Aegean

October 19, 2025

by Julius

Greece

A Journey Through Blue and White

There’s a reason sailors return to the Cyclades year after year. This route from Lavrion or Athens weaves through turquoise bays, whitewashed villages, and the pure Aegean light that defines Greece. The wind here has a name — the Meltemi — and it shapes every moment at sea. From May to October, the Cyclades offer perfect sailing, though July and August bring stronger northerly gusts that test both skill and spirit.

The Route: Island by Island

Day 1 – Lavrion to Kea (20 NM)
Set sail from the mainland and watch Athens fade behind you. Kea welcomes you with calm anchorages and golden beaches. It’s the perfect first stop — relaxed, close, and distinctly Cycladic.

Day 2 – Kea to Kythnos (25 NM)
Sail south to Kythnos, a quiet gem known for its thermal springs in Loutra and small, friendly harbors. Drop anchor in Kolona Bay, where a narrow sandbar connects two curves of turquoise water — one of the most photogenic spots in the Aegean.

Day 3 – Kythnos to Serifos (20 NM)
Serifos rises steeply from the sea, its hilltop town gleaming white against the rock. Wander through cobbled alleys, have dinner in a taverna overlooking the bay, and feel time slow down.

Day 4 – Serifos to Sifnos (20 NM)
The rhythm of sailing settles in. You reach Sifnos — chic yet traditional — with perfect beaches and local cuisine that ranks among the best in the Cyclades. Try chickpea stew or a glass of cold white wine by the harbor in Kamares.

Day 5 – Sifnos to Syros (35 NM)
A longer passage brings you to Syros, the elegant capital of the Cyclades. Ermoupoli’s neoclassical architecture and vibrant waterfront tell a different story — one of history, trade, and style.

Day 6 – Syros to Kea (35 NM)
Turn north again. The Meltemi may push from behind as you sail back toward Kea, retracing your route but seeing it anew — the islands now familiar, the sea more trusted.

Day 7 – Kea to Lavrion (20 NM)
Your final sail brings you home. The mainland grows on the horizon, but the Aegean stays with you — in your skin, your mind, your sails.

Why Sail the Cyclades

Few routes capture Greece’s essence like this one. Every island feels unique, yet together they form a rhythm — white villages, deep blue anchorages, simple food, and the eternal wind. Whether you chase adventure or calm, the Cyclades deliver both.

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