On the move: Sailing the Cyclades Islands, Greece

Sailing in the Cyclades, Greece

We have been sailing on Dutch waters for about 3 years now, but we this year we decided to go on a bigger sailing adventure by chartering a boat in Greece and sail around the Cyclades Islands. The Cyclades Islands are a group of islands in the Aegean Sea, southeast of mainland Greece going all the way further southeast to Santorini and Anafi.

We had in mind that we would start the journey going southeast to reach Santorini as fastest and earliest possible, and then to make a round trip back slowly, one island at the time, against the prevailing northern wind. We have 2 weeks to do this, and it should’ve been a feasible route which will allow us to have adequate time to enjoy not only the sailing, but also the islands themselves.

We chartered our 33-feet boat, Arethusa, from a marina in Lavrio, a small port town an hour away from Athens. She’s slightly bigger than our own boat, but still a manageable size for a 2.5-person crew to handle and a comfortable size to live in for the next 2 weeks.

As always, you can never plan a sailing trip in details. To sail is to learn to live the moment and to go along with nature, however fickle she can be. During our trip, the wind we expected actually came from the opposite direction. Sometimes it disappeared altogether (which made the sails useless), sometimes it’s blowing in gale force (which promises exciting sailing, albeit bumpy and potentially dangerous one). In the middle of our trip, we had to abandon our intention to go to Santorini and instead, we opted to go the more sensible route of going to the northern islands. We could’ve sailed stubbornly upwind and reach Santorini, but we decided to go along with the wind and waves for a more pleasant journey. But we’re glad we did, as we discovered other islands, each special in their own ways, away from the crowds of the more popular southern islands.

In the end, we managed to hop through 7 islands  (Kythnos, Paros, Naxos, Mykonos, Tinos, Andros and Kea), stayed in 9 harbours and clocked in 190 Nautical miles (approx. 350 km) in the log book within 14 days. One phone was lost at sea, many bruises were had, but otherwise it was a a wonderful experience for the whole family. Follow our journey and the islands in detail in separate posts:

Coincidentally, The Daily Post’s Photo Challenge theme of the week is “On the move”.

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15 thoughts on “On the move: Sailing the Cyclades Islands, Greece

  1. Oh, I am sooo jealous! Everything looks so wonderful there, and so clean and pretty. I am really impressed, I’ve never been to Greece.
    Just a question, on Sunday were are opening our blog TravelBloggers.on.WordPress to the public. We have now a slider on our front page. It’s possible to feature up to 6 pictures there. I am still looking for more pictures, would you like one of yours to be featured there on opening day (with a link to your blog)? I thought of the one with the famous windmills of Mykonos.

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    1. Greece is wonderful. Even if you’re not sailing, I would really recommend visiting these islands (some have airports).

      Regarding the pictures, I take it you changed your mind and prefer the beach picture? 😉

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      1. Hi Cherrie, thanks for the permission to use your photos. I will either take both or one, I have to see if they are suitable for our slider. The other thing: Where was the beach picture taken?

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    1. The Cyclades is not the easiest to sail, but I do think it’s the most rewarding water to do so. It’s so beautiful, nice weather, wonderful people, great food. I miss it already!

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  2. This looks like such a wonderful sailing trip. I’ve never sailed before – I get sea sick easily – but definitely, it’s hard to predict what will happen during the course of such an adventure. The worst part would probably be losing your sail. I guess for most part of the trip, you see mainly the ocean most of the time but it’s very rewarding when you get to your destination. Great photos, love them all 🙂

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    1. Thanks for stopping by!

      I have never sailed long distance in the open sea as well, the trip we did in Greece was mostly short sail between the islands, taking between 2-6 hours of the day. My biggest worry when sailing is having somebody fallen overboard, since it can be difficult to retrieve them back, especially in a rough sea. The sail itself is always secured solidly to the boat, and if you lose it anyway you can still use the engine to continue.

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      1. Yeah, falling over board can be common in sailing as the waves usually push boat unpredictably around, making you lose your balance. I would assume you all had safety jackets on at all times, so you would have felt safer. Without the sail, you may be in for a wild ride 🙂

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  3. these are amazing and beautiful images… makes me wanna check travel ops to the Cyclades first thing in the morning 🙂 love the one with the white houses and the red trees… almost surreal…

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    1. The islands are amazing. Some of the bigger ones have airports as well, I’m sure you’ve got more flight options from Bulgaria since it’s not so far. I would recommend flying to Naxos, which is located strategically in the middle of the Cyclades and then take the ferries to surrounding islands.

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      1. thanks for the tip 🙂 funny thing, it’s not so far, but I’ve been to Greece only twice so far… will have to remedy that… 🙂

        once again, gorgeous post!!

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