Sailing Greek Islands – West Cyclades Route

Join a sailing adventure in Greece

Sailing Holidays greece, West cyclades

Cyclades is the region where Greek Islands holidays concept was born. It is where whitewashed houses with cupolas, blue window shutters and small fishermen boats were photographed first. From here these photographs spread throughout the world and now in every Greek holidays prospect you can see photos from the Cyclades.

The islands in this area are rather large but with rich coastline with plenty of bays to drop our anchor in. Most of these bays are lined with some small, white houses, sandy beach and rather arid hills encircling it. The water is crystal clear, tavernas are in every town and the life runs somewhat slower. It is not easy to get to these places as a tourist – one needs to take a ferry – so the tourism is somewhat less (except Mykonos of course).

These Cycladic islands were inhabited already a few thousands of years ago and it can be seen and felt. Columns, ruins, old paths are visible here and there, sometimes in the most unexpected place. Delos archeological site is on the UNESCO list and as it bears signs of life from 3000BC is a unique place. Luckily enough plenty of great anchorages are nearby. Seems ancient Greeks also loved sailing (our thesis).

join a sailing adventure into the Greek islands

We designed a longer than usual sailing route, ca. 180NM, to visit all the gems of the region. This route will give you a great insight into what Cyclades have to offer: little and quiet Greek villages, islander towns, archeological sites, lonesome bays and wind, wind, wind. Meltemi, the prevailent wind, will make sure the longer distance of this route will be covered with ease. Pack your sun lotion as the wind, sun and no clouds is to be expected.

As always no sailing experience is needed to join as our professional skippers will introduce you to everything you need to know. The optional sailing course is absolutely free of charge, hands on and fun. More experienced sailors will be given some responsibility and can count on coaching too!

Feel invited to join us sailing in Greece, West Cyclades! And remember to check our other Greek sailing holidays.

“West Cyclades” Route

⛵ 7 nights sailing,
☸️ professional skipper, 
🏨 bed linen, towels, end cleaning,
🏄 SUP board and dinghy,
🔒 trustful damage deposit,
💎 travel insurance.

💰 cashbox contribution ca. 180 € pp (food, port fees, fuel),
✈️ flights/transfers.

Departure: Lavrion Port
Nearest Airport: Athens (ATH).

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*To sail at other dates; to organize a private trip; to get in touch.

A windy ride!

Cyclades region is known for it’s Meltemi wind. As our local sources state this is somewhat changing with the global climate change. However, it is still likely that we may ride the wild wind for a day or two. Do not worry, if the forecast will be too much, we stay put in port and enjoy the holidays on land.

Sunsets on Greek Islands

Sailing through the Greek Islands we have many chances to admire picturesque sunsets. Some in a lonesome bay, some on a hilltop with whitewashed houses around. In any case bring your favourite drink along, the magic is there.

History alive

On each Greek Island you can find remnants of history enclosed in a stone. Standing there sometimes for thousands of years already they are witnesses for passing time and a great way to touch the antiquity. On West Cyclades sailing trip the special highlight is Delos archeological site. Naturally a refreshing swim before and after the visit is a must!

Seaside Tavernas

The best way to conclude a day of sailing in Greece is with some Greek food. And the most charming way is to visit a local taverna, very often situated just at the seaside or overlooking the port. Fishermen boats that in the morning brought the days catch are laying tied up and provide a beautiful background for a dinner we enjoy with our new sailing friends.

Highlights of Sailing Holidays in Greece, West Cyclades Route

What you can expect to do on this route.

Itinerary for Sailing Holidays in greece

We are true to the discoverers` spirit and plan our adventures accordingly to the winds, the weather and your wishes. This means the order as well as some of stopovers may be different than presented below. Leave planning at home! The plan showed below is only an indicative itinerary and your trip may differ. Only the mad men sail against the wind!



Our meeting point is not far from Athens and even closer to the Athens Airport (ATH). In a small coastal Greek town, we all meet, provision the boats, get to know each other on a Welcome Dinner and spend the first night on a boat. On the next day, Sunday, our Greek sailing adventure truly begins. We do the safety introduction, cast off lines, set sails and off we go! Into the Cyclades!



One of the typical islands in the Cyclades with a Hora on the top of the hill. Hora is the term used for the “old town” in Greece. After a sailing day we approach the port of Serifos, moor and strengthten ourselves with a delicious Greek meal. For the ones who would like to explore the island a pleasant hike is within sight – hiking up to the Hora and admiring the view on the port and our boats.



A wonderful anchorage awaits. The small sandy beach separates two perfect bays. We drop anchor, raft up the yachts and enjoy the typical evening of shared food, fun, and night swimming. 



Syros is one of the larger towns on our route. This is chance to sneak a peek into the islanders lifestyle who are not living in a small village. A regular ferry connection exists between Athens and Syros. Strolling the streets of this town we will, at least for one day, experience how it is to live on a greek island. Little cafes are bustling with life, people go about their own agenda and we can soak the sun and enjoy people and architecture watching. A Hora-hike is also available!



This is a perfect example of a Greek anchorage. Crystal clear water, sandy bottom, secured from the wind. We spend a night anchored, swimming, relaxing and simply enjoying the beauty of the nature around. At night, the stars come out and hopefully we will see a shooting star or two.



This is apparently one of the most visited Greek islands of all. Let us see why! Expect tourist crowds but also beatiful old town with charm and splendor. A sunset at the old windmills is apparently a must.



On Friday, the last day of our sailing trip, we have a regatta. Skippers will have taught you enough by now to let you sail the boat yourself. They are there to observe and help in emergencies but it is you and your crew who competes against the other crews.

Once the rush and excitement is over, we have the Captains Dinner (“the last dinner”) with all the crews and enjoy recalling stories from the last week, toasting for the regatta winners and savoring the last moments under the sails.





Keep the connection

Day 8 is the day to say goodbye. All the miles sailed, bays visited, skills gained and time shared with others will make us bond and build relationships. Cherish these, keep in touch and remember that your sailing tribe is there. See you another time!

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