Cyclades yacht charter itineraries.
Pick your week from Cyclades.
Greece · Cyclades sailing area
Pick a starting point
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.
See day-by-day →
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.
See day-by-day →
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.
See day-by-day →
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.
See day-by-day →
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.
See day-by-day →
Athens → Saronic gulf (14 day) → 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.
See day-by-day →
Paros → Siros → Milos → Ios (14 days) → Paros
A 14-day round-trip from Paros through Sifnos, Syros, Mykonos, Naxos, Ios, Santorini, Folegandros and Milos: the full Cyclades grand tour.
See day-by-day →
Paros → Milos → Santorini → Syros (14 days) → 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.
See day-by-day →
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.
See day-by-day →
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.
See day-by-day →
Paros → Naxos → Schoinousa → Paros
Sail a week from Paros through Naxos, Donousa, Koufonisia, Schoinousa and Irakleia, the quietest anchorages in the Small Cyclades.
See day-by-day →
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.
See day-by-day →
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.
See day-by-day →
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.
See day-by-day →
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.
See day-by-day →
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.
See day-by-day →
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.
See day-by-day →
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.
See day-by-day →
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.
See day-by-day →
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.
See day-by-day →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.
Like one of these routes?
See which boats are available from this area's marinas for your dates — live prices, real availability, online booking.