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The second week of my flotilla from Athens in October 2026: six boats, around 150 nautical miles and plenty of sunshine. From Alimos Marina we sailed via Cape Sounion, Kea and Loutra on Kythnos to Sifnos and Serifos. Each crew sailed its own boat, while I was reachable by radio and sent out the route, weather and recommendations every morning and evening. We also enjoyed a campfire on the beach of a secluded bay on Sifnos.

Sailing area: Mediterranean, Aegean
Country: Greece, Southern Europe
Departure: Alimos Marina (Athens)
Destination: Alimos Marina (Athens)
Route: Alimos Marina (Athens) → Cape Sounion → Korissia (Kea) → Karthaia, Poles Bay (Kea) → Loutra (Kythnos) → Anchorage on Sifnos → Chora (Serifos) → Kolona (Kythnos) → Alimos Marina (Athens)
Nautical miles: 150
Travel dates: 17.10.2026 – 24.10.2026
Sailing yacht: Monohull, Dufour 470, 47 ft
Charter company: Istion
Organiser: Mit Pablo um die Welt

From 17 to 24 October 2026 I was out in the western Cyclades with a flotilla of six boats, starting from Alimos Marina. We covered around 150 nautical miles that week. Four couples in their sixties joined me on board my Dufour 470 from Istion as cabin charter guests. I especially like crews like this: considerate, in good spirits, and everyone pitches in.

Two weeks in October, two sailing areas

This was my second flotilla week. The first was demanding in terms of weather, and we had to stay in a safe harbour for a day or two. We therefore kept to the Saronic Gulf, where there are plenty of sheltered bays and short hops.

In the second week the weather was much more settled, so we headed for the western Cyclades. Everything is more spread out there, it is quiet, and the wind tends to be a little stronger. We still had rather too little of it, but plenty of sunshine. You can't have everything when sailing.

Alimos Marina and Cape Sounion

We set off from Alimos Marina in Athens. The first waypoint was Cape Sounion with the Temple of Poseidon, the classic start to a sailing trip towards the Cyclades.

Korissia on Kea

On Kea we spent the night in the small harbour of Korissia. For the first leg into the Cyclades the island is ideally placed, as it is the nearest major stop from Attica.

Karthaia in Poles Bay

We then continued to the far side of Kea, on the southeast coast. In Poles Bay lie the remains of the ancient city of Karthaia, one of the island's four cities. Quite a lot can still be seen of the Temple of Apollo and the Temple of Athena, dating from around 530 to 500 BC. The site is hard to reach overland, but from the water it lies right on your route.

Loutra on Kythnos

Loutra is one of my favourite places in the Cyclades. The reason is the hot springs, which have made this little village on Kythnos famous. After a day on the water, there is hardly anything better.

A secluded anchorage on Sifnos

Further south, we anchored together as a flotilla in a secluded bay on Sifnos. On the beach we lit a campfire and tidied up a little while we were at it. A wonderful evening.

Chora on Serifos

In Chora, the village high above the harbour of Serifos, everything had already shut up for the night. It is still beautiful there. For a sailing trip in the second half of October, though, it means this: don't count on tavernas and shops being open on the small islands.

Kolona on Kythnos

On a lovely day's sailing we headed back to Kythnos, to the twin bay of Kolona. A narrow strip of sand connects the island there with the islet of Agios Loukas and divides the water into two bays. Both are sheltered from the Meltemi and from southerly winds. From here we sailed back to Alimos Marina.

How the flotilla worked

My concept is simple: each crew sails its own boat and makes its own decisions. Morning and evening, everyone gets an update from me on the route, weather and recommendations, and I can always be reached by radio. Anyone who likes can simply follow me. Anyone who prefers to go their own way can head off for two or three days and rejoin us later in harbour.

That is exactly how it turned out. I was constantly under way with two or three boats. Two others did their own thing from the third day, because they wanted to sail more. Even so, we would sit down together in a restaurant in the evening, go our separate ways the next day and meet again on the beach the day after.

The feedback was clear. The crews appreciated the safety net and knew that I was there whenever they needed me. There is no pre-booked table where everyone has to sit every evening. Everything is planned, and yet each boat remains its own master.

The crews learned a lot too, because they had to make their own decisions on board. We settled the most important questions over the radio: How much anchor chain should I pay out? How do I position the boat so that I fit exactly into the gap? There was the odd tip on mooring as well.

Conclusion

Athens is a very good sailing area for a flotilla in October, because you can change plans depending on the weather. If conditions are unsettled, you stay in the Saronic Gulf with its short hops and sheltered bays. If the weather is settled, the western Cyclades are open to you. A flotilla is right for you if you want to skipper your own boat and keep learning, while having someone at your side who knows the sailing area inside out and also passes on tips on restaurants and places to visit.

In 2027 I am once again offering two flotillas from Alimos Marina: 2 to 9 October and 9 to 16 October 2027. From 28 August to 4 September 2027, a family flotilla also departs from Corfu, my home waters. My Google reviews will give you a good impression. Feel free to write to me, even if you just want tips and tricks for the sailing areas in Greece.