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

Greece:

Cyclades

Duration:

4 days - 4 nights

Max number of passengers:

11 people

Available:

October

Suitable for travellers:

> 18 years

Boarding from:

Lávrio

What's included

Cancellation policy

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Organised by:

George A.

Member since 2020 -

Organisation

English

Greek

French

Romanian

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

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41+

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Boat & Classes of Service

Ocean Yachts Ocean Star 56 - 2002

Type

Sailboat

Length

16 m.

Toilets

4

Cabins

6

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10+

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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

The itinerary may be subject to changes due to weather conditions and/or technical or logistical reasons, in order to ensure safety and a pleasant sailing experience for all participants.

Frequent questions

The organiser reviews

avatar image

Organised by:

George A.

Member since 2020 -

Organisation

English

Greek

French

Romanian

4.5/5

out of

12

reviews

Skipper

Boat

Destination

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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.
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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 :)
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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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SHARE & SAIL: explore Cyclades with new friends

05/25/2022

Louise A.

-

France

The cruise went very well throughout the week. The organization was there on board, good swimming spots and good taverns in the evening. We had to adapt the program according to the weather (which is normal with a sailing cruise) and unfortunately could not do much sailing (no wind and then too much wind). Thank you so much George and Fotis for everything.

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