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SHARE & SAIL: explore Cyclades with new friends




7 days - 7 nights

Max number of passengers:

11 people



Boarding from:

Finikas, Syros, Greece

What's included

Cancellation policy

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Organised by:

George A.

Member since 2020 -






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10 travellers have already tried this experience

This experience, in a nutshell

NB: The remaining two places are for two women, in a triple cabin to be shared with another woman!

A carefully crafted sailing holiday for singles, couples and small group of friends who are open to meet new faces and share the fun.

The trip starts from Syros island, right in the heart of Cyclades offering safe and comfortable passages to the most stunning hidden gems.

Each day brings us on a different Cycladic island, with sailing time from 2-4hrs.
Plenty of time during the day to swim, snorkel, enjoy the Greek sun and the crystal clear water anchored in selected bays. The evenings will find us in picturesque villages, exploring ashore, with various optional activities. Each day ends with a delicious meal based on the recognised Greek cuisine.

Unparalleled comfort on a large and carefully maintained 56ft sailing yacht. The layout offers maximum privacy featuring 5 cabins for guests, each with its own WC.

George, your greek skipper and local guide is big part of the success of this trip. Positive, friendly, knowledgable, with a very personal and professional approach!
Day 1
Welcome to Syros right at the heart of Cyclades. We are equally excited and looking forward to spending an unforgeable sailing week together around the hidden gems of the Greek islands.
Arriving at the beautiful Finikas Marina where our trip starts, you can drop your luggage at the boat and enjoy a splash in the nearby crystal clear water or a tasteful lunch right in front of the marina, awaiting the check-in time, which is at 14:00. Everyone is on board and after our 30min briefing we sail out to Serifos island.
Our first swim stop takes place in the beautiful beach of Psili Ammos following an anchorage at Livadi bay. We enjoy the local cuisine for our dinner at the little port village of Serifos, reachable by dinghy.

Day 2
We wake up at Serifos bay and after breakfast there is an optional activity of walking up to the top of Chora, the main Serifos village with the breathtaking view. We sail out to Sifnos later in the afternoon, just after our swim and lunch. Arriving at Vathi of Sifnos we enjoy our evening swimming and later find ourselves around the table of beautiful seafront taverna discussing the day’s highlights.

Day 3
First thing in the morning after breakfast is getting a short bus ride to Artemonas to experience the whitewashed path to nearby Apollonia, the capital of Sifnos. After enjoying our coffee with locals a short taxi ride to the famous Castro with a limitless view to blue of the Aegean Sea. We head back to the boat for sailing out after lunch. Passing by Despotiko we reach the south bays of Antiparos for a refreshing splash in the crystal clear water and a seafront dinner hard to forget

Day 4
Taking advantage of the morning wind we sail to Iraklia island. A population of approximately 80 people during the winter, kept this little paradise off the beaten tack of mainstream tourism. Enjoy a really picturesque place. Relaxing on the beach, having drinks with view to the boat, walking at the top of the hill for the sunset. The team will gather for an unforgettable dinner in a family tavern, experiencing the Greek hospitality and approachability.

Day 5
Koufonisi is our next destination, just a few nautical miles away for our morning relaxing sail. Grab your towel and explore the simply stunning island. Walking north on the coastline you experience the one of a kind magic beaches, you take a dip in natural lagoon made of rocks, try the local snacks at Pori beach at the very north of the island. Enjoy this well-deserved blessed piece of land.

Day 6
Early start to Naxos, the largest -in surface- island of the Cyclades. An endless sandy beach on the west side of the island and the sea front picturesque main village. No doubt you could literally spend days and days to explore. Take a glimpse to the Greek history walking up the white washed alleys, experience history, art, different tastes of local goodies, discover inspired gifts for your beloved ones back home. Rent bike and reach the nearby beaches, let your skipper organise windsurfing lessons for you or a half day road trip to the inland villages. After a whole day exploring we gather all for our dinner, sharing the fun, the thoughts and the highlights.

Day 7
Off we go to nearby Paros. Enjoy the sandy beaches of the island. You can optionally experience water sports or just enjoy the Greek sun on the beach or on deck. A few hours later, sailing for lunch to Ermoupoli the capital of Cyclades your skipper drops you so that you take full advantage of the day and sails the boat to Finikas Marina, where you will rejoin late in the evening for dinner.
Ermoupoli with its 19th-century architecture, is always full of life. Explore the pedestrianized streets and some of the finest tastes in Cyclades. You can optionally visit Ano Hora, the old town on the top of the hill. The end of the day will find you all back to Finikas for your last dinner in front of the water.

Day 8
Time to say goodbye. Sharing and sailing a full week in all those new fascinating places created new friends and triggered lifetime unforgettable memories.
Morning 08:30am we do checkout at Marina Finikas of Syros just where we started. We will help you with your luggage to the taxi which can take you to Syros airport or ferry station at Ermoupoli.
We can optionally organise for you a private sea transfer to Athens (2hrs) or any other island with our in-house all-weather motor boat.

No Departures available

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Boat & Classes of Service

Ocean Yachts Ocean Star 56 - 2002




16 m.





Our itinerary

Our trip starts here:

Finikas, Syros, Greece.

from 12:00

to 14:00

Our trip ends here:

Finikas, Syros, Greece.

from 8:00

to 9:00

The organiser reviews

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Organised by:

George A.

Member since 2020 -







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SHARE & SAIL: explore Cyclades with new friends


Monica F.



We had the absolute best time on our trip and would 100% recommend this to anyone looking to explore the Greek Islands. Orestis was the best skipper, very attentive and knowledgeable and willing to join in on the fun. We had a great crew who were up for the adventure and really loved the sailing aspect along with all the challenges that come with it. If you’re looking for a hands on, real down to earth experience then this would definitely be for you. This trip was the highlight of our time in Greece! Thank you Orestis and George :)
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SHARE & SAIL: explore Cyclades with new friends


Gaëlle F.



Un séjour dont je me souviendrai longtemps. Cette navigation au cœur des petites Cyclades avant la pleine saison était dépaysante et ressourçante. George a su faire preuve d'une présence et communication remarquables avant de nous confier au skipper de la navigation. Au-delà du confort et de la beauté du voilier, nous avons gouté à l'authenticité de la Grèce, à la convivialité et fluidité de la vie en mer. Découverte de petits paradis perdus, exploration des grottes et des grands bleus, charme des petits villages et saveurs des tavernes traditionnelles. Le skipper Fotis K. a su nous partager ses talents de navigation, son amour de l'eau, et le lifestyle grec avec beaucoup de passion et d'humilité. Nous n'aurons pu rêver mieux, pour plonger au cœur de cette culture singulière qui vit avec la mer. Une expérience unique que je recommanderai à toutes les personnes en recherche d'immersion, d'exploration et de douceur de vivre. Merci à tous, c'était magique.
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SHARE & SAIL: explore Cyclades with new friends


Louise A.



La croisière s’est très bien passée tout au long de la semaine. L’organisation était au rendez vous à bord, bons spot de baignade et bonnes tavernes le soir. Nous avons dû adapté le programme en fonction de la météo (ce qui est normal avec une croisière à la voile) et n’avons malheureusement pas pu faire beaucoup de voile (absence de vent puis trop de vent). Merci beaucoup George et Fotis pour tout.
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SHARE & SAIL: explore Cyclades with new friends


Gulnaar Z.


United Kingdom

There were so many things wrong with this sail trip that it’s hard to know where to begin. Luckily the other folks on board and the Cyclades themselves were amazing, so it was possible to have a sense of humour about the whole thing. I didn't find George a reliable person. George wasn’t on board! But he doesn’t bother to tell you that. His description of the trip and what to expect is misleading in many respects, eg “I offer carefully crafted sailing holidays for everyone, always doing the extra step and with a very personal service” Several people on the boat raised various serious and legitimate complaints with George both during and after the trip. I had the feeling that safety procedures were not observed. There was no safety briefing, and we weren’t even told where the life jackets were or what to do if something happened to the skipper. For me: to avoid! There are other operators you could choose. ---------- *GEORGE'S RESPONSE* Miss G Z thank you very much for your feedback. We take any feedback very seriously, especially any negative one. The process of listening with attention to each customer helps us understand whether we are performing -as we usually feel we do - or there are things which could be done better. On the other hand -fortunately very rarely- negative reviews like this present one, are clearly just related to traveller's failed attempt to get free holidays. The so-called revenge reviews. On day 2, Miss G Z complained about an itinerary change which was imposed by the weather and happened clearly in favour of the group’s experience and safety. I personally responded immediately to this complaint, did every extra step -even crossed 40nm in rough seas with a motorboat to meet G Z in person - to understand better her specific expectations from the group-shared sailing experience, she had joined just the previous day. When G Z did not show up to this meeting and instead sent us an sms asking for money it became very clear that she was just after free holidays and not after a professional and uncompromised service, as we do offer since 2010. Some booking engines choose to firewall revenge reviews as fake and misleading and others -like Sailsquare- choose to publish and let the reader filter by themselves. The good part of this latter approach is that it reconfirms the authenticity of all reviews, including all the 5-star ones. George

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