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

Greece:

Cyclades

Duration:

9 days - 9 nights

Max number of passengers:

8 people

Available:

-

Suitable for travellers:

> 10 years

Boarding from:

Athens

What's included

Cancellation policy

avatar image

Organised by:

George A.

Member since 2020 -

Organisation

English

Greek

French

Romanian

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.

No Departures available

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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

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.

What's included in the price

•

Boat equipment and facilities

    Final cleaning

    Tender and outboard

•

Onboard staff

    Skipper

•

Taxes, fees and moorings

    Mooring fees

•

Transport

    Fuel (boat/tender)

What you'll have to pay during the experience

Below are the additional expenses you will incur during the experience.

Common Fund

€50 - €100 Per person

On Day one we create as a group a food kitty. All passengers puts in 50e each, in cash with which we do our provisioning from the local supermarket for breakfast & lunch. If needed during the trip we put in 20euro-max 50euro each more.

    Galley

    Food for the skipper

What's NOT included in the price

Below are the services that are not included in the price of the experience, including any available optional services that you may pay directly to the organiser (we advise you to inform the organiser prior to departure in case you wish to purchase such services and arrange the payment terms directly with him).

Excluded

    Bedding kit

    Towels kit

    Meals/drinks consumed ashore

Frequent questions

The organiser reviews

avatar image

Organised by:

George A.

Member since 2020 -

Organisation

English

Greek

French

Romanian

4.5/5

out of

13

reviews

Skipper

Boat

Destination

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

10/18/2025

Tina F.

-

Germany

I very much liked the Mixture of sailing, stops for swimming, attractions and good food in the Taverns. The boat was very comfortable and well-equiped. Orestis Was very friendly, Attentive and professional. It was perfect and I would love to do another Trip in future.
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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
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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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