The Western Cyclades by Sailboat: Milos, Sifnos, Folegandros

Weather month by month

Day by day

Day 1, Lavrion to Kythnos, 25 NM, ~5 h

Anchorage: Kolona bay (a double sand spit joining two shores, an emblematic anchorage) or Merichas harbour.

Ashore: the Loutra thermal springs, tavernas at Merichas.

Day 2, Kythnos to Serifos, 22 NM, ~4-5 h

Anchorage: Livadi, the main sheltered harbour, with the Chora above.

Ashore: a tiered Chora, one of the most photogenic in the Cyclades.

Day 3, Serifos to Sifnos, 15 NM, ~3 h

Photo: Kamares, Sifnos · Gaetano Cessati / Unsplash

Anchorage: Kamares harbour, or the enclosed, well-sheltered Vathi bay.

Ashore: Sifnos, the gastronomic capital of the Cyclades; the villages of Apollonia and Kastro.

Day 4, Sifnos to Milos, 20 NM, ~4 h

Photo: Milos · Artem R / Unsplash

Anchorage: Adamas, a large harbour in an enclosed bay, one of the best shelters in the Cyclades; water, fuel, provisions.

Ashore: Sarakiniko, a white lunar landscape; the catacombs; the village of Plaka.

Warning: the bay of Milos is vast but the entrance can be windy in a Meltemi.

Day 5, Milos, a tour of the island, 15 NM

Sailing / anchorage: round to the Kleftiko caves (lava arches, turquoise water, a daytime stop) and Firiplaka beach.

Ashore: back to Adamas for the night.

Warning: Kleftiko is exposed, fair weather only.

Day 6, Milos to Folegandros, 22 NM, ~4-5 h

Photo: Folegandros · Tom Waldek / Unsplash

Anchorage: Karavostasi (small harbour) or coves on the east coast.

Ashore: the cliff-top Chora, one of the finest in Greece, and the church of Panagia overlooking the void.

Day 7, Folegandros to Lavrion, 60 NM, a long leg

Sailing: a big beat back north against the Meltemi. Break it via Serifos or Kythnos if the wind builds, or plan a night passage in settled weather. An early start is essential.

Summary table

Practical checklist

• Licence: coastal licence plus ICC plus VHF Short Range Certificate.
• Provisioning: water and fuel at Adamas (Milos) and the main harbours; scarce at the smaller anchorages.
• TEPAI and the usual papers.

Booking and preparation

• Compare boats available from Lavrion or Piraeus.
• Charter insurance recommended.
• Flights: to Athens (ATH); one-way return from Milos (MLO) possible.
• Shore activities: the Kleftiko caves, Sarakiniko, tastings in Sifnos.

See also: the guide Sailing the Cyclades and the article How much does a week's sailing in Greece cost.

Nautical data: western Cyclades distance tables, harbour offices of Milos and Sifnos. Weather: HNMS. Kleftiko and Kolona anchorages to be judged on the day's weather.

A word from the crew

Logbook. Milos is a palette: Sarakiniko white as the moon, Kleftiko and its translucent caves. We once let a whole day slip by in the dinghy, drifting from one arch to the next.

The mistake to avoid. Counting on Kleftiko for the night. The site is stunning but completely open: it's a daytime stop. Sleep in Adamas or in a sheltered cove of Poliegos.

Our favourite, and what we skip. Favourite: the Poliegos anchorage, unreal water and nobody there. What we skip: the packed harbours in August, the western Cyclades are best lived at anchor.

Our verdict. Beauty 5/5. Anchorages 4/5. Ease 3/5. Crowds 2/5. Verdict: the gentle alternative to the central Cyclades, wilder and often better sheltered.