Sailsquare | N°1 in Europe for sailing and catamaran holidays

George A.

Provider type:

Organisation

City:

Syros

Member since:

2020

421 Sailsquare travellers have been on board my experiences

My experiences

4.5

CYCLADIC ESCAPE - Active Holidays: 5 days Sailing & Exploring Unknown Greece

Greece: Cyclades

4 days - 4 nights

One departure available

October

€790

Per person

About us

I offer carefully crafted sailing holidays for everyone, always doing the extra step and with a very personal service. Everything happens on my own Ocean Star 56ft monohull, the perfect yacht for the mission due to the seaworthiness, space and flexible layout with 5cabins/5WCs + skipper amenities

My sailing areas

Cyclades

Greece

Cyclades

Greece

My boats

Type

Sailboat

Length

16 m.

Toilets

Cabins

Show all

Travel with peace of mind

Total transparency

Want to avoid surprises? Find out before you book who your skipper and fellow travellers will be. Do you have questions or doubts? Send a message to the skipper!

Flexible cancellation

Cancel within 30 days of departure for any reason and receive a full refund. Want even more? Purchase the extension to cancel your booking until your departure.

Constant support

Our dedicated multilingual support team is always ready to assist you, before and during your holiday, and is always in touch with the skippers we work with.

Reviews

4.5/5

out of

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.