SHARE & SAIL: explore Cyclades with new friends
Greece:
Cyclades
Duration:
6 days - 6 nights
Max number of passengers:
10 people
Available:
-
Boarding from:
Finikas, Syros, Greece
What's included
Cancellation policy
Organised by:
George A.
Member since 2020 -
Organisation
English
Greek
French
Romanian
This experience, in a nutshell
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 1-4hrs.
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.
All trips are powered by George and skippered by a hand-picked Well-trained skipper from his team. The skipper 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 13:30 at the all-day restaurant Baobab. Your skipper will search for you. Everyone is on board and after our short briefing we sail out towards Paros island.
Our first anchorage is at the bay of Naousa or in the port of Naousa. We enjoy the local cuisine for our dinner at the little port village
Day 2
Taking advantage of the morning wind we sail to Iraklia island just after breakfast. 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 3
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 4
A morning swim or walk on the beautiful coastline of Koufonisi is great way to start your day. Today we will be sailing to the third special member of the Small Cyclades named Schinousa. The beauty of this place cannot be described with words. The protected waters of this passage offers a perfect sailing arena, a great place to understand why people for in love with sailing. At your arrival in the small picturesque port of Schinousa, you can choose from swimming in the the nearby beach, explore the village at the top of the hill or enjoy the sun and the tranquil atmosphere on the boat. A seafront dinner for all the group at the end of the day.
Day 5
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 6
Off we go towards Syros. Enjoy an interim relaxing swim stop. A few hours later, we arrive for lunch to Ermoupoli the capital of Cyclades your skipper drops you so that you take full advantage of the day and takes 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 7
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.
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 1-4hrs.
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.
All trips are powered by George and skippered by a hand-picked Well-trained skipper from his team. The skipper 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 13:30 at the all-day restaurant Baobab. Your skipper will search for you. Everyone is on board and after our short briefing we sail out towards Paros island.
Our first anchorage is at the bay of Naousa or in the port of Naousa. We enjoy the local cuisine for our dinner at the little port village
Day 2
Taking advantage of the morning wind we sail to Iraklia island just after breakfast. 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 3
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 4
A morning swim or walk on the beautiful coastline of Koufonisi is great way to start your day. Today we will be sailing to the third special member of the Small Cyclades named Schinousa. The beauty of this place cannot be described with words. The protected waters of this passage offers a perfect sailing arena, a great place to understand why people for in love with sailing. At your arrival in the small picturesque port of Schinousa, you can choose from swimming in the the nearby beach, explore the village at the top of the hill or enjoy the sun and the tranquil atmosphere on the boat. A seafront dinner for all the group at the end of the day.
Day 5
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 6
Off we go towards Syros. Enjoy an interim relaxing swim stop. A few hours later, we arrive for lunch to Ermoupoli the capital of Cyclades your skipper drops you so that you take full advantage of the day and takes 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 7
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.
Boat & Classes of Service
Ocean Yachts Ocean Star 56 - 2002
Type
Sailboat
Length
16 m.
Toilets
4
Cabins
6
10+
Show all
Our itinerary
Our trip starts here:
Finikas, Syros, Greece.
Check-in: 1:00 PM
Our trip ends here:
Finikas, Syros, Greece.
Check-out: 8:00 AM
The organiser reviews
Organised by:
George A.
Member since 2020 -
Organisation
English
Greek
French
Romanian
4.5/5
out of
13
reviews
Skipper
Boat
Destination
SHARE & SAIL - 6 days Exploring & Relaxing at the heart of Cyclades
08/2/2025
Filippo F.
-
Italy
The islands visited and the sea were truly splendid. For this reason alone, the holiday was worth it. The boat was large, in good condition, but perhaps there were a few too many of us to fully enjoy the spaces: even on the foredeck it was difficult to find room for everyone, and with five women on board, that area was often off limits.
The skipper proved to be competent and serious even though it was not George and it is fair to say that because we only found out once we got on the boat. Too bad for never having done the roadstead, the proposed tour was beautiful but it seemed a bit like a tour de force with a very tight schedule of arrivals and departures from the various ports, something that had never happened to me in other boat holidays because generally because of the philosophy of the trip we have always been a bit free to decide whether to do port or to anchor, when to leave and when to stop if we saw something interesting.
In addition, the total absence of wind forced us to always move with the engine, which took away part of the charm of sailing.
In general, though, the atmosphere was friendly, and everyone behaved with kindness. If I had to recommend George, I would say that he is a reliable person
SHARE & SAIL - 6 days Exploring & Relaxing at the heart of Cyclades
07/22/2025
Manuel R.
-
Canada
Very nice first sailing experience for our family, the Skipper was perfect (Franco Greek), advised us on the best destinations in the small Cyclades. The sailboat was very good and functional. Thank you to Georges for the welcome and the organization. I recommend this experience to visit the islands in the best way.
SHARE & SAIL: explore Cyclades with new friends
10/10/2023
Monica F.
-
Australia
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 :)
SHARE & SAIL: explore Cyclades with new friends
05/26/2022
Gaëlle F.
-
Réunion
A stay that I will remember for a long time.
This navigation in the heart of the small Cyclades before the high season was exotic and rejuvenating. George was able to show a remarkable presence and communication before entrusting us to the skipper of the navigation. Beyond the comfort and beauty of the sailboat, we tasted the authenticity of Greece, the conviviality and fluidity of life at sea. Discovery of small lost paradises, exploration of caves and big blues, charm of small villages and flavors of traditional taverns. The skipper Fotis K. was able to share with us his sailing talents, his love of the water, and the Greek lifestyle with a lot of passion and humility. We could not have dreamed of a better way to dive into the heart of this singular culture that lives with the sea. A unique experience that I will recommend to all people looking for immersion, exploration and the sweetness of life. Thank you all, it was magical.
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