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

Weather month by month

The two-week route

Highlights

Delos, Apollo's sacred island, a major archaeological site reached by tender from Mykonos, an open-air museum in the middle of the Aegean.

The Little Cyclades (Koufonissia, Iraklia) are the wild counterpoint to the archipelago's stars: translucent water, harbour tavernas, silence.

Photo: Amorgos · Iason Raissis / Unsplash

Amorgos and its cliff-clinging Chozoviotissa monastery, one of the strong images of the Cyclades.

Photo: Oia, Santorini · Anastasios Tselepatiotis / Unsplash

Santorini, the arrival in the volcanic caldera, the summit of the trip, best savoured over a full day from Oia to Ammoudi.

Photo: Folegandros · Henry Lim / Unsplash

The western return (Folegandros, Sifnos, Serifos) closes the loop through the gentler, more gastronomic western Cyclades.

Technical points and cautions

• Santorini: you cannot anchor in the caldera (300 to 400 m deep). Spend the night at Vlychada marina (south) or the Thirassia anchorage. A venturi effect is possible between the walls.
• Day 14: a long beat back to Lavrion against the Meltemi. Break it via Serifos and Kythnos, or plan a night passage in settled weather.
• Weather buffer: keep two flexible days out of fourteen. The Meltemi can pin down a leg; Milos and Sifnos are western refuges.

Practical checklist

• Licence: coastal licence plus ICC plus VHF Short Range Certificate.
• Provisioning: water and fuel at the larger harbours (Syros, Paros, Naxos, Adamas); scarce at the islets.
• TEPAI and the usual papers.

Booking and preparation

• Compare boats available from Lavrion.
• Charter insurance recommended.
• Flights: to Athens (ATH); one-way returns from the islands possible.
• Shore activities: Delos, the Oia sunset at Santorini, 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: Cyclades distance tables, archipelago harbour offices. Weather: HNMS. Santorini and islet anchorages to be confirmed with the weather and an up-to-date pilot.

A word from the crew

Logbook. Two weeks is the luxury of slowing down: pushing on to Anafi or Sikinos, the islands a single week forces you to skip, and watching the Meltemi set the rhythm of the days rather than enduring it.

The mistake to avoid. Trying to tick everything off. Over a fortnight the temptation is to pile on the miles; the Meltemi lays down the law, keep two days of slack and prefer to see an island twice than miss three.

Our favourite, and what we skip. Favourite: the Little Cyclades and Amorgos, far from the bustle. What we skip: Mykonos in high summer, its mooring prices and its crowds; a quick call is enough.

Our verdict. Beauty 5/5. Anchorages 4/5. Ease 3/5. Crowds 3/5. Verdict: the grand tour that shows the Cyclades in every shade, from postcard to desert.