Two weeks to complete the grand tour of the Cyclades, from Lavrion to Mykonos and on to Santorini, through the great landmark islands and the confidential islets. It is the most complete circuit in the Aegean, demanding in the Meltemi but unforgettable. Around 340 miles, with real weather windows to manage. Detail below.
In brief
| Item | Detail |
|---|---|
| Base | Lavrion (Athens) |
| Access | Fly to Athens (ATH), base ~45 min |
| Total distance | ~340 NM |
| Sailing time | ~68 h over 14 days |
| Duration | 14 days / 13 nights |
| Level | Confident (sustained Meltemi, long legs) |
| Recommended boat | 44-50 ft monohull (windward ability) |
| Best time | June and September |
| Winds | Meltemi N-NNW, 20-30 kt in Jul-Aug |
| Indicative budget | ~1,500 to 2,600 € per person over two weeks (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 · Syros · Mykonos · Delos · Paros · Naxos · Koufonisia · Amorgos · Ios · Santorini · Folegandros · Sifnos · Serifos
Weather month by month
| Month | Meltemi | Air | Sea | Note |
|---|---|---|---|---|
| May | Light to moderate | 22-24° | 18-19° | Cool water |
| June | Moderate | 26-28° | 21-22° | Ideal |
| July | Strong (20-30 kt) | 29-31° | 23-24° | Confident crews |
| August | Strong to very strong | 29-31° | 24-25° | Weather margin essential |
| September | Easing | 26-28° | 23-24° | Ideal |
| October | Variable | 22-24° | 21-22° | End of season |
The two-week route
| Day | Leg | NM | Anchorage | Shelter |
|---|---|---|---|---|
| D1 | Lavrion to Kythnos | 25 | Kolona / Merichas | Good |
| D2 | Kythnos to Syros | 22 | Ermoupoli | Good |
| D3 | Syros to Mykonos | 20 | Ornos / harbour | Moderate |
| D4 | Mykonos, Delos | 12 | Mykonos | Moderate |
| D5 | Mykonos to Paros | 25 | Naoussa / Parikia | Moderate |
| D6 | Paros to Naxos | 12 | Naxos town | Moderate |
| D7 | Naxos to Koufonissia | 18 | Koufonissia | Good |
| D8 | Koufonissia to Amorgos | 20 | Katapola | Very good |
| D9 | Amorgos to Ios | 30 | Ormos Iou | Very good |
| D10 | Ios to Santorini | 20 | Vlychada / Thirassia | Good |
| D11 | Santorini, day ashore | 0 | as D10 | n/a |
| D12 | Santorini to Folegandros | 22 | Karavostasi | Moderate |
| D13 | Folegandros to Sifnos | 25 | Kamares / Vathi | Very good |
| D14 | Sifnos, Serifos, Lavrion | ~55 | split or night | n/a |
| Total | ~340 |
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.
Amorgos and its cliff-clinging Chozoviotissa monastery, one of the strong images of the Cyclades.
Santorini, the arrival in the volcanic caldera, the summit of the trip, best savoured over a full day from Oia to Ammoudi.
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.
