header cover

SECRET ODYSSEY - Active Holidays: 5 days Sailing & Exploring Unknown Greece

Next Departure:

April 17, 2025

Greece:

Cyclades

Duration:

4 days - 4 nights

Max number of passengers:

11 people

Available:

April - October

Suitable for travellers:

> 18 years

Boarding from:

Lávrio

What's included

Cancellation policy

avatar image

Organised by:

George A.

Member since 2020 -

Organisation

Romanian

French

Greek

English

avatar placeholder
avatar placeholder
avatar placeholder

18 travellers have chosen this experience

This experience, in a nutshell

This exhilarating sailing adventure is designed for active explorers who are eager to step outside their comfort zones.


Whether it's learning to sail, stand-up paddle boarding in secluded bays, or snorkeling in crystal-clear waters, each day offers a hands-on experience that brings you closer to the stunning beauty of the Aegean Sea.


Combining exciting activities with moments of peaceful reflection in nature, this journey allows you to fully immerse yourself in the history, culture, and wild beauty of the Cycladic islands, all while pushing your boundaries and embracing the unknown.


The less known Greek islands are the perfect sailing arena for our unforgettable escape.

€790

4 days - 4 nights

experience image 0experience image 1
experience image 2
experience image 3

41+

Show all

Boat & Classes of Service

Ocean Yachts Ocean Star 56 - 2002

Type

Sailboat

Length

16 m.

Toilets

4

Cabins

6

boat image 0boat image 1
boat image 2
boat image 3

10+

Show all

Our itinerary

Our trip starts here:

Lávrio.

Check-in: 3:00 PM

Our trip ends here:

Lávrio.

Check-out: 1:00 PM

Leg 1

Day 1: Lavrio to Kea

The thrill of boarding your private yacht and setting sail toward Kea sets a perfect start to your journey. As you cruise through the sparkling waters of the Aegean, excitement builds with the stunning views. Upon arrival in Kea, you’ll have the chance to explore the island’s charming village, followed by a delightful dinner at a local taverna, where authentic Greek flavors and warm hospitality welcome you to the heart of the islands.

Day 1: Lavrio to Kea

Leg 2

Day 2: Kea to Kythnos

For those seeking a refreshing start, a morning run (if you wish) along Kea’s serene coastline is an invigorating way to prepare for the day ahead. Afterward, set sail once again, stopping to swim in the ancient bay near Tetrapolis, where history and natural beauty intertwine. As you sail toward Kythnos, your skipper will teach you the basics of sailing, making this leg both educational and exciting. End the day soaking in Kythnos’ famous warm springs before enjoying a seafront dinner, easing into the relaxed rhythm of island life.

Day 2: Kea to Kythnos

Leg 3

Day 3: Kythnos to Serifos

Start your day with some morning stretching on Loutra Beach, where you’ll face the rising sun over the Aegean. The sail to Serifos provides another opportunity to practice sailing under the guidance of your skipper. Upon arriving at Serifos, spend the afternoon paddleboarding in a secluded bay or simply relaxing onboard, fully immersed in the peaceful atmosphere. A team-prepared dinner under the stars will bring the day to a gentle, restful close.

Day 3: Kythnos to Serifos

Leg 4

Day 4: Serifos to Kythnos

Take the morning to explore the picturesque Chora of Serifos, where vibrant bougainvillea lines the whitewashed streets. Discover the breathtaking views from the Ag. Konstantinos chapel, or simply relax at the peaceful Livadi and Livadaki beaches. Later, sail back to Kythnos to visit its iconic Apokrousi and Kolona beaches. With a glass of wine in hand, enjoy the golden hues of the setting sun on the water, a perfect ending to an active and fulfilling day with a dinner on board.

Day 4: Serifos to Kythnos

Leg 5

Day 5: Kythnos to Lavrio

As your journey draws to a close, enjoy one last morning swim or paddle boarding session in the calm waters of Kythnos. The sail back to Lavrio is a time to savor the final moments, reflecting the rich experiences, and the sense of accomplishment that comes from exploring both the sea and the islands.


This remarkable voyage blends active exploration of hidden gems, historical discovery, relaxation, and the pure joy of being out on the open sea, offering an unforgettable experience that captures the true spirit of the Aegean islands.

Day 5: Kythnos to Lavrio

Frequent questions

The organiser reviews

avatar image

Organised by:

George A.

Member since 2020 -

Organisation

Romanian

French

Greek

English

4.5/5

out of

11

reviews

Skipper

avatar placeholder

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 :)
avatar image

SHARE & SAIL: explore Cyclades with new friends

05/26/2022

Gaëlle F.

-

Réunion

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.
avatar image

SHARE & SAIL: explore Cyclades with new friends

05/25/2022

Louise A.

-

France

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.
avatar placeholder

SHARE & SAIL: explore Cyclades with new friends

11/21/2021

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

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaAmerican ExpressApple pay

© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964