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DOWNWIND BLAST: One-way Cycladic Adventure Athens to Santorini, 10days

Next Departure:

April 4, 2025

Greece:

Cyclades

Duration:

9 days - 9 nights

Max number of passengers:

8 people

Available:

April - October

Suitable for travellers:

> 10 years

Boarding from:

Athens

What's included

Cancellation policy

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Organised by:

George A.

Member since 2020 -

Organisation

French

English

Romanian

Greek

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24 travellers have chosen this experience

This experience, in a nutshell

This is an exhilarating sailing adventure on a carefully designed route: One-way Downwind sailing Athens to Santorini


Designed for active explorers who would like to visit the Greek islands in the most exciting way. Given the prevailing winds during the Greek summer are 90% north (Athens) to south (Santorini), then this is going to be downwind sailing fun, getting from one island to the next just with the power of the wind.


Included optional activities on this unforgettable journey are introduction-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 sailing, optional activities with peaceful moments on board or on the islands, this journey offers the best balance between fully immersing yourself in the destination, exploring the local history, culture, and wild beauty of the Cycladic islands, while pushing your boundaries and embracing the unknown.


We depart from Lavrio port (35min from Athens International Airport by taxi or uber) and end the trip at Santorini. Our disembarkation happens on 10th day morning of the experience at Ios island. The last leg Ios to Santorini happens by a 55min ferry ride which is the most comfortable way to reach Santorini. Ferry ticket Ios to Santorini is included in the price.  


Staying 1-2 extra nights at Santorini exploring the breathtaking views, tasting the fine wines and visiting the prehistoric town of Akrotiri is highly recommended. 


The less known Greek islands in between Athens and Santorini are the perfect sailing arena for this lifetime sailing journey.

€1,980

9 days - 9 nights

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33+

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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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9+

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Our itinerary

Our trip starts here:

Athens.

Check-in: 3:00 PM

Our trip ends here:

Santorini Harbour.

Check-out: 9:00 AM

Leg 1

Day 1: Lavrio to Kea

Begin your journey with excitement as you board your private yacht in Lavrio and set sail toward Kea. Glide across sparkling waters, taking in stunning views of the Aegean. Upon arrival in Kea, explore the charming village before enjoying an authentic Greek dinner at a local taverna.


Day 1: Lavrio to Kea

Leg 2

Day 2: Kea to Kythnos

Start the day with an optional morning run along Kea’s serene coastline. Sail to the ancient bay of Tetrapolis for a refreshing swim, combining history with natural beauty. As you journey to Kythnos, learn the basics of sailing under the guidance of your skipper. End the day soaking in Kythnos’ famous thermal springs before dining by the sea.

Day 2: Kea to Kythnos

Leg 3

Day 3: Kythnos to Serifos

Greet the sunrise stretching on Loutra beach before setting sail to Serifos. The journey offers another chance to enhance your sailing skills. In Serifos, spend the afternoon paddleboarding in a tranquil bay or relaxing on deck. Conclude the day with a team-prepared dinner under the stars.

Day 3: Kythnos to Serifos

Leg 4

Day 4: Serifos to Sifnos

Explore the picturesque Chora of Serifos in the morning, wandering its whitewashed streets and enjoying panoramic views from Agios Konstantinos chapel. Sail to Sifnos, known for its iconic Vathi Bay. Relax on the beach, sip wine, and savor a delicious seaside dinner at a local taverna.

Day 4: Serifos to Sifnos

Leg 5

Day 5: Sifnos to Antiparos

Sail on a fun beam reach to the serene bay between Antiparos and Despotiko. The day is dedicated to relaxation, with opportunities for swimming, sunbathing, or reading. In the evening, enjoy a beachfront seafood lunch and paddleboarding sessions. Experience the magic of a Cycladic sunset, either from the water or with a glass of wine on deck.

Day 5: Sifnos to Antiparos

Leg 6

Day 6: Antiparos to Iraklia

Set out early for a day of adventure, beginning with a swim stop at Panteronisi’s turquoise waters. Sail to the remote island of Iraklia, where tranquility and natural beauty abound. Discover its pristine beaches and charming village before dining at a family-run taverna featuring fresh, local flavors.

Day 6: Antiparos to Iraklia

Leg 7

Day 7: Iraklia to Koufonisi

A short sail brings you to Koufonisi, a hidden gem of the Small Cyclades. Explore on foot or by e-bike, reveling in sandy beaches, clear waters, and a vibrant village. Savor delicious local food, indulge in unforgettable ice cream, and experience a lively nightlife.


Day 7: Iraklia to Koufonisi

Leg 8

Day 8: Koufonisi to Schinousa

Begin the day exploring South Naxos or Kato Koufonisi, swimming in caves and tranquil beaches. Sail to Schinousa, ending the day in a secluded bay. Prepare and share a group dinner onboard, enjoying the serenity of this peaceful island.


Day 8: Koufonisi to Schinousa

Leg 9

Day 9: Schinousa to Ios

Sail downwind to Ios, stopping at Maganari Beach for a final swim in pristine waters. Reflect on the journey as you arrive at Ios Port. Celebrate your adventure with a memorable dinner, sharing stories of your sailing accomplishments and the connections made along the way.

Day 9: Schinousa to Ios

Leg 10

Day 10: Ios to Santorini

Bid farewell to your skipper and crew as you disembark at Ios. Take the included ferry to Santorini, a 55-minute journey offering stunning views. Spend extra time in Santorini to explore its breathtaking cliffs, taste fine wines, and visit historical sites like Akrotiri.


Day 10: Ios to Santorini

Frequent questions

The organiser reviews

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Organised by:

George A.

Member since 2020 -

Organisation

French

English

Romanian

Greek

4.5/5

out of

11

reviews

Skipper

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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

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

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.
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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

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