Sailing the Cyclades

Season : May to OctoberLevel : Intermediate to advancedWind : Meltemi NE, force 4–7 in summer

The Cyclades are an archipelago you have to earn. In July and August the meltemi funnels down from the northeast at force 4–7, kicks up a short sea and turns every passage into a proper beat or a fast reach. That is exactly their charm: here, you really sail.

Our advice after several seasons: build your route downwind (south on the way out, back via the better-sheltered islands), keep a spare day before hand-over, and favour anchorages on the islands' southwest coasts when the meltemi is established.

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Route

The itineraries — Cyclades

Weekend

Option 1 — Lavrio › Kea › Kythnos, round trip

The best fun-to-logistics ratio in the Cyclades: Lavrio is 40 minutes from the airport and Kea a 12-mile reach away. Ideal to sample the archipelago over three days without committing to long passages.

Day	Leg	Distance	Highlights
Day 1	Lavrio › Kea (Vourkari)	12 nm	Late-morning start, anchor or quay at Vourkari, dinner at Aristos.
Day 2	Kea › Kythnos (Kolona Bay)	16 nm	Kolona's double beach, one of the Aegean's finest anchorages. Arrive before 3 pm to claim a spot.
Day 3	Kythnos › Lavrio	26 nm	A beat home if the meltemi is in — leave early, the sea builds in the afternoon.

7 days

Option 2 — Western Cyclades loop from Athens

Our reference route: Kythnos, Syros, Paros, Sifnos and Serifos in one week, roughly 190 miles all told. Full day-by-day detail in the dedicated itinerary below.

Day	Leg	Distance	Highlights
Days 1–2	Alimos › Kythnos › Syros	64 nm	Two solid legs to reach the heart of the archipelago.
Days 3–5	Syros › Paros › Sifnos	55 nm	Naoussa, then the bays of Sifnos — the mellowest part of the week.
Days 6–7	Sifnos › Serifos › Kythnos › Alimos	75 nm	The climb home in two stages with a buffer night at Kythnos before hand-over.

See the full day-by-day itinerary →

When to go

When to go — Cyclades

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Advice from sailors

Guides & articles — Cyclades

ItineraryCyclades

14-Day Grand Tour of the Cyclades: Lavrion to Mykonos and Santorini

Lavrion to Mykonos and Santorini: two weeks for the most complete sailing circuit in the Aegean.

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ItineraryCyclades

7-Day Cyclades Itinerary: Paros to Santorini

Paros to Santorini's caldera in 7 days: the signature Cyclades sailing loop, day by day.

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ItineraryCyclades

7-Day Central Cyclades from Mykonos: Delos, Paros, Naxos, Little Cyclades

Delos, Paros, Naxos and the Little Cyclades in a week from Mykonos, without the hard beat from Santorini.

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ItineraryCyclades

The Western Cyclades by Sailboat: Milos, Sifnos, Folegandros

Milos, Sifnos, Folegandros: the quiet side of the Cyclades, away from the crowds, in 7 days from Lavrion.

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GuideCyclades

Sailing the Cyclades: Everything to Know Before You Go

Meltemi, seasons, charter bases and itineraries: everything to know before sailing the Cyclades.

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Frequently asked questions

Does the meltemi make the Cyclades dangerous?

No, but it demands discipline: check forecasts every evening, leave early, reef before the channels between islands where the wind accelerates by 10 knots. In a strong meltemi (force 7+), you stay put at anchor — that is part of cruising too.

Which island is the best starting point?

Kythnos. At 26 miles from Lavrio and 38 from Alimos, it offers three safe anchorages whatever the wind (Kolona, Loutra, Merichas) and sets the tone of the archipelago without commitment.

Monohull or catamaran for the Cyclades?

A 40–45 ft monohull for us: it points better upwind (essential with the meltemi) and squeezes into small harbours more easily. A catamaran makes sense off-season or on a downwind-biased route.