ItineraryGreece sailing routes

Cyclades yacht charter itineraries.

20 routes

Pick your week from Cyclades.

Greece · Cyclades sailing area

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7-day loop

Route 01 · From Athens

Athens → Mykonos → Paros → Athens

Sail seven days round-trip from Athens through the Cyclades: Kea, Syros, Mykonos, Paros, Serifos and Kythnos, with anchorages, tavernas and mooring tips.

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7-day loop

Route 02 · From Athens

Athens → Kea → Syros → Hydra → Athens

Sail seven days from Athens through the Cyclades and Saronic: Cape Sounion, Kea, Syros, Serifos, Hydra and Poros, the route map's most varied winds.

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Athens → Mykonos → Santorini → Paros → Athens

14-day loop

Route 03 · From Athens

Athens → Mykonos → Santorini → Paros → Athens

Sail a 14-day Cyclades loop from Athens through Mykonos, Paros and Santorini, back via Milos and Sifnos. Anchorages, mooring and wind, day by day.

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7-day loop

Route 04 · From Athens

Athens → Saronic gulf → Athens

Round-trip yacht charter from Athens through the Saronic Gulf: Aegina, Poros, Spetses, Hydra and Agistri. Short hops, sheltered water, easy mooring.

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7-day loop

Route 05 · From Athens

Athens → Saronic gulf → Poros → Athens

Round-trip yacht charter from Athens through the Saronic: Aegina, Poros, Ermioni, Methana, Palaia Epidavros and Agistri, temples and calm sailing.

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14-day loop

Route 06 · From Athens

Athens → Saronic gulf → Athens

Sail 14 days from Athens through the Saronic Gulf to medieval Monemvasia and back via Hydra, with quiet Peloponnese anchorages and famous fortress towns.

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14-day loop

Route 07 · From Paros

Paros → Siros → Milos → Ios → Paros

A 14-day round-trip from Paros through Sifnos, Syros, Mykonos, Naxos, Ios, Santorini, Folegandros and Milos: the full Cyclades grand tour.

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Paros → Milos → Santorini → Syros → Paros

14-day loop

Route 08 · From Paros

Paros → Milos → Santorini → Syros → Paros

Two weeks under sail from Paros: Naxos, the Small Cyclades, Santorini, Milos, Sifnos, Kythnos and Syros before the run home. A full Cyclades circuit.

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14-day loop

Route 09 · From Santorini

Santorini → Mykonos → Milos → Santorini

Round-trip yacht charter from Santorini: Milos, Sifnos, Syros, Tinos, Mykonos, Amorgos, the Small Cyclades and Naxos across two weeks of Aegean sailing.

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7-day loop

Route 10 · From Paros

Paros → Ios → Santorini → Paros

Sail seven days from Paros through Ios and Santorini, looping home via Folegandros and Sifnos. A compact southern Cyclades run for Meltemi-ready crews.

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7-day loop

Route 11 · From Paros

Paros → Naxos → Schoinousa → Paros

Sail a week from Paros through Naxos, Donousa, Koufonisia, Schoinousa and Irakleia, the quietest anchorages in the Small Cyclades.

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7-day loop

Route 12 · From Paros

Paros → Syros → Mykonos → Paros

A week-long sailing loop from Paros through Sifnos, Syros, Tinos and Mykonos: sheltered swim bays, marble villages and easy town quays in the Cyclades.

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7-day loop

Route 13 · From Santorini

Santorini → Milos → Paros → Santorini

Sail a week from Santorini through Ios, Paros, Serifos, Sifnos and Milos, then home. A southern-Cyclades loop of caldera cliffs and volcanic bays.

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14-day loop

Route 14 · From Lavrion

Lavrion → Milos → Sifnos → Lavrion

A two-week sail from Lavrion through Andros, Tinos and the Small Cyclades, looping back via Milos and Sifnos. Remote anchorages and real island tavernas.

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14-day loop

Route 15 · From Lavrion

Lavrion → Mykonos → Santorini → Lavrion

Sail 14 days from Lavrion through Syros, Tinos, Mykonos and Santorini, then loop home via Milos and Sifnos. Central Cyclades, minimal motoring.

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14-day loop

Route 16 · From Mykonos

Mykonos → Naxos → Paros → Kea → Mykonos

A two-week Cyclades circuit out of Mykonos, calling at Naxos, Paros, Milos, Sifnos, Serifos, Kythnos, Kea, Andros, Tinos and Syros.

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Lavrion → Kea → Kythnos → Sifnos → Lavrion

7-day loop

Route 17 · From Lavrion

Lavrion → Kea → Kythnos → Sifnos → Lavrion

Sail a 7-day round trip from Lavrion through Kea, Kythnos, Sifnos and Serifos: thermal springs, quiet quays and the finest cooking in the Cyclades.

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7-day loop

Route 18 · From Lavrion

Lavrion → Mykonos → Paros → Lavrion

Sail a seven-day loop from Lavrion through Kea, Syros, Mykonos, Paros, Serifos and Kythnos, mixing famous harbours with quiet Cycladic anchorages.

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7-day loop

Route 19 · From Mykonos

Mykonos → Kea → Syros → Mykonos

Sail a week from Mykonos through Tinos, Andros, Kea, Kythnos and Syros: marble villages, thermal springs and the grand harbour of Ermoupoli.

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7-day loop

Route 20 · From Mykonos

Mykonos → Naxos → Paros → Mykonos

Sail a 7-day charter loop from Mykonos through Naxos, Paros, Sifnos, Serifos and Syros, a central Cyclades route with the Meltemi at your back.

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About Cyclades

Cyclades, in a sailor's words.

The Cyclades are the postcard — Mykonos windmills, Santorini's caldera, chapels on bare hills — but they're also the Aegean's most honest sailing. In July and August the meltemi blows a hard 20–30 knots from the north for days at a time, which turns passages into proper sailing and rewards crews who plan around it. Go south with it, not against it; leave early; treat rest days as part of the route. June and September soften everything. Paros and Naxos make the best mid-week bases, with real towns behind the quays, and Lavrio spares you an hour of Athens traffic on day one. This is the area for crews who want the sailing itself to be the story.