Breeze & Sail
Itinerary

The Western Cyclades by Sailboat: Milos, Sifnos, Folegandros

By Brieg Lecoublet · Updated 11 August 2026 · 5 min read

Mykonos windmills in the Cyclades
Illustrative photo: Mykonos · Larry Ebbs / Unsplash

The western Cyclades are the archipelago's quiet side: Milos and its lava caves, gourmet Sifnos, and Folegandros with its cliff-hung Chora. A gentler Meltemi than the centre, spectacular anchorages, and far fewer crowds than Mykonos or Santorini. Around 180 nautical miles from Lavrion, day by day.

In brief

ItemDetail
BaseLavrion (Athens) or Piraeus
AccessFly to Athens (ATH), base ~45 min
Total distance~180 NM (loop)
Sailing time~36 h over 7 days
Duration7 days / 6 nights
LevelIntermediate (gentler than the central Cyclades)
Recommended boat40-46 ft monohull or catamaran
Best timeJune and September
WindsMeltemi N-NNW, a touch lighter than the central Cyclades
Indicative budget~750 to 1,150 € per person (see Sailing budget in Greece)

Explore the stops

Approximate destination locations for trip planning. Use current nautical charts and local information for navigation.

Lavrion · Kythnos · Serifos · Sifnos · Milos · Folegandros

Weather month by month

MonthMeltemiAirSeaNote
MayLight to moderate22-24°18-19°Few crowds
JuneModerate26-28°21-22°Ideal
JulyStrong29-31°23-24°Meltemi present
AugustStrong29-31°24-25°Book early
SeptemberEasing26-28°23-24°Ideal
OctoberVariable22-24°21-22°End of season

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

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

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

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

DayLegNMTime (~5 kn)AnchorageShelter
D1Lavrion to Kythnos25~5 hKolona / MerichasGood
D2Kythnos to Serifos22~4-5 hLivadiGood
D3Serifos to Sifnos15~3 hKamares / VathiVery good
D4Sifnos to Milos20~4 hAdamasExcellent
D5Tour of Milos15~3 hAdamasExcellent
D6Milos to Folegandros22~4-5 hKaravostasiModerate
D7Folegandros to Lavrion60longbasen/a
Total~180~36 h

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.

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Frequently asked questions

Is it easier than the central Cyclades?

A little: the Meltemi is slightly lighter and there are more sheltered anchorages (Adamas, Vathi). The final beat home is still demanding.

Why the west rather than Santorini?

For the calm, the volcanic landscapes of Milos and the food of Sifnos, away from the crowds.

Can the long Day 7 be avoided?

Yes, with a one-way charter from Milos (MLO airport) or by breaking the return.

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The author

Brieg Lecoublet — Skipper and sailor

Offshore licence holder, French State sailing instructor, Formula 18 racer qualified for the World Championship, former instructor at UCPA Bombannes. He has personally sailed every Breeze & Sail route. Over 5,000 miles logged since 2012.

Keep reading: Sailing holidays in Greece · Sailing the Cyclades