This is the big-ticket Cyclades week: Athens to Mykonos and Santorini and back, with Kea, Syros, Delos, Naxos, Sifnos and Kythnos along the way. It covers roughly 250 nautical miles in seven days, so we sell it almost exclusively on motor yachts — the distances that would exhaust a sailing week become comfortable three-to-four-hour runs at 20 knots. If you want the two famous islands in one week without flying between them, this is the route.
The week runs Saturday to Saturday: board Saturday afternoon in Athens, hand back the following Saturday morning, seven nights on board. Your captain adjusts the order and the swim stops to the meltemi — treat the days below as the shape of the week, not a fixed schedule.
The route at a glance
- Day 1: Board in Athens — evening in Plaka
- Day 2: Athens to Sounion and Kea (~40nm)
- Day 3: Kea to Syros (~38nm)
- Day 4: Syros to Delos and Mykonos (~28nm)
- Day 5: Mykonos to Naxos and Santorini (~65nm) — the long day
- Day 6: Santorini to Sifnos (~50nm)
- Day 7: Sifnos to Kythnos and Athens (~75nm) — the run home
Day 1 – Board in Athens
Embarkation is Saturday afternoon at Alimos or Agios Kosmas marina, a short transfer from the airport. If you can, arrive a day early and stay in Plaka — the Acropolis, a taverna dinner inside the old town, and a proper night’s sleep set the week up better than a rushed same-day arrival. Once aboard, meet the crew, settle in, and save your energy: tomorrow the distances start.
Day 2 – Athens to Sounion and Kea (~40nm)
A short first hop down the Attica coast to Cape Sounion, where the Temple of Poseidon stands on the cliff above a wide, easy anchorage. Go ashore for the twenty-minute walk up — it is the best-placed temple in Greece and the crowds are thinner in the morning — or watch it from the sundeck while lunch is served. In the afternoon you cross to Kea, the closest true Cyclade to the mainland, for a quiet first island night in Vourkari harbor among a handful of local fish tavernas.
Day 3 – Kea to Syros (~38nm)
A morning of water toys in Kea’s protected bay — this is usually the day the jet skis and paddleboards come down — then an afternoon run to Syros, the administrative capital of the Cyclades. Ermoupolis is unlike anywhere else in the islands: a real working Greek city with neoclassical squares, an opera house, and a harborfront built by 19th-century shipping money. Dinner ashore here feels genuinely local because it is — Syros does not live off tourism.
Day 4 – Syros to Delos and Mykonos (~28nm)
This is the day the Cyclades earn their name. The islands form a rough circle — kykloi — around Delos, the sacred island at their center, and its ruins are one of the great archaeological sites of Greece. Anchor off, go ashore early before the heat and the day boats, and give it two hours. From Delos it is a short hop into Mykonos for the evening: dinner in the old town, the windmills at sunset, and as much or as little nightlife as your group wants. We pre-book restaurants here in peak months — walk-ins are genuinely hard in July and August.
Day 5 – Mykonos to Naxos and Santorini (~65nm)
The longest day of the week, and we plan it deliberately: an early start, a mid-day stop in Naxos, and a sunset arrival into Santorini. Naxos harbor sits right under the Portara — the massive marble doorway of the unfinished Temple of Apollo — and the old town behind it has stayed remarkably untouristed. Back aboard for the afternoon crossing, you arrive at the Santorini caldera as the light goes gold, which is the single best way to see it. Overnight per your captain’s call — the caldera is exposed, so many crews position to Vlychada or stay only as conditions allow.
Day 6 – Santorini to Sifnos (~50nm)
The morning belongs to Santorini: the hot springs at Nea Kameni in the middle of the caldera, a swim off the volcanic islets, and time ashore in Oia or Fira if you did not go up the evening before. After lunch you cross northwest to Sifnos — the food island of the Cyclades, with a handsome hilltop Chora and some of the best tavernas in the Aegean. It is also the decompression stop this route needs after the Mykonos–Santorini stretch.
Day 7 – Sifnos to Kythnos and Athens (~75nm)
The run home, broken exactly where it should be: Kolona beach on Kythnos, a double-sided sandbar connecting the island to a rocky islet, and one of the best swim stops in the western Cyclades. Lunch at anchor, a last session on the water toys, and then the final leg back to Athens for your last night on board. Disembarkation is Saturday morning after breakfast.
How to make this week work
Be honest with yourself about pace: this route trades lazy mornings for the two most famous islands in Greece plus five quieter ones. It needs a motor yacht with legs — we usually recommend 20+ knots of cruising speed — and it rewards groups who want to see a lot. If your ideal week is two islands and long afternoons at anchor, tell us and we will slow this down to a Saronic or western Cyclades route instead. And in high summer, the meltemi can reorder these days — your captain will run the exposed legs early in the morning when the wind is lowest.
Prefer fewer miles with the same postcard views? Our Mykonos round trip and Santorini round trip both start on the island instead of sailing to it.
Talk to a Yacht Charter Expert
Finding the right yacht is one of the most important parts of the whole charter process, and one of the easiest places to go wrong without the right guidance.
That is where our experience matters. We know how to look beyond the listing, spot the differences that matter, and shortlist yachts that are a strong fit for the group, the budget, and the kind of trip you actually want to have.
If you are planning a charter in Greece, we would be happy to help you find the right yacht.
