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Sailing in the eastern Aegean, between the Dodecanese and the Cyclades!

Greece:

Dodecanese

Duration:

8 days - 8 nights

Max number of passengers:

8 people

Available:

September

Suitable for travellers:

10 - 70 years

Boarding from:

Kalymnos

What's included

Cancellation policy

avatar image

Super!

Organised by:

Andrea S.

Member since 2014 -

Organisation

Italian

Spanish

English

This experience, in a nutshell

lorem ipsum loremScattered off the coast of Turkey, the islands that form the Dodecanese constitute the southernmost and most cosmopolitan archipelago, with architectural features of clear oriental influence. They were the last territories to be incorporated into modern Greece.

The Dodecanese (Kos, Kalymnos, Leros, Lipsi, Patmos) and the Southern Sporades (Ikaria, Fourni and Samos) offer a great variety of natural scenery and activities: beaches equipped for every sport, safe and solitary landings, caves and fjords, high and green mountains. The itinerary is very varied, some islands are parched and barren, others green and fertile and rich in water springs. All the islands are wonderful, each with its own grace, each with its own story.


Under a great sun, carried by the wind, from port to port, from cove to cove, we will discover the villages and landings of these Aegean islands: white villages clinging to the rock that look at you from above, jagged coasts, intense light and sun, a crystal clear sea, churches, castles and monasteries, together with a warm welcome. These are the Greek Islands, which in mythology gave birth to heroes and gods.


The itinerary is very rich and admits many variations: a holiday of ten nights will allow us to travel without being pressed by the need to travel many miles. We will alternate days of longer sailing with days that only require a short sea ride and we will allow ourselves stops on land (Fourni and / or Ikaria) to go and browse on land and explore the islands by bike, car or by renting scooters, stretch our legs and enjoy some well-deserved relaxation and refreshing baths in the most beautiful coves.


The actual route will be decided on the spot based on weather conditions, listening to everyone's preferences but on the unquestionable decision of the Captain, who aims to ensure a pleasant and safe itinerary.

In case of adverse weather conditions that cannot be circumvented, the crossing between the Dodecanese and the Cyclades will take place further south and the crew will be disembarked in Naxos, from where they can easily reach Mykonos by ferry.


No previous experience is needed, but this holiday is suitable for a young crew, with good agility and physical fitness, a lover of the sea, sailing and travel.


The following itinerary is therefore indicative.

€650

8 days - 8 nights

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14+

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Boat & Classes of Service

Beneteau Oceanis Clipper 500 - 1991

Type

Sailboat

Length

15.3 m.

Toilets

3

Cabins

3

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18+

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Our itinerary

Our trip starts here:

Kalymnos.

Check-in: 5:00 PM

Our trip ends here:

Mykonos.

Check-out: 8:00 AM

Our itinerary

From 5 p.m. boarding begins, you get on board, arrange your luggage and make the first common shopping (galley), which will then be replenished during the journey where necessary. In the evening we go out for dinner in a local tavern and we start to get to know each other.

After visiting Kalymnos, the next morning we go out to sea and continue our ascent northwards: in a zigzag path that will take us to a bay where we will have lunch and relax for a break and a nice swim. Continue to Leros, heading to the charming village of Pandeli, for an aperitif with a breathtaking view!


Early in the morning we set sail for Lipsi, continue north and head for Patmos.

After visiting Patmos with its castle-monastery, we take the sea again and head for Fourni, the island with the strange shape of a lobster, jagged, and off the beaten track.

We reach the nearby Ikaria and its beautiful beaches on the southern side, crystal clear water and very few visitors, a true paradise.

The next day a nice sail to Mykonos awaits us .

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

Super!

Organised by:

Andrea S.

Member since 2014 -

Organisation

Italian

Spanish

English

5.0/5

out of

47

reviews

Skipper

Boat

Destination

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Heart of the Cyclades Cruise: Milos to Mykonos

07/13/2025

Marta A.

-

Spain

🤍💙
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Heart of the Cyclades Cruise: Milos to Mykonos

07/12/2025

Annalisa M.

-

United Kingdom

A beautiful trip completely met my expectations, Andrea with his professionalism handled all situations excellently.
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From the Dodecanese to the Cyclades: sailing off the beaten track!

07/7/2025

Farida B.

-

Italy

The 10 days on a sailing boat were beautiful. An experience that filled my eyes and heart... it would not have been such if I had not sailed in the company of beautiful people with whom a pleasant connection was created. I thank the "Super Skipper Andrea", a professional: competent, reliable and generous. A holiday that I recommend to those who love the sea and freedom!
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From the Dodecanese to the Cyclades: sailing off the beaten track!

06/30/2025

elisabetta m.

-

Italy

Andrea is a professional, always ready to make you happy! We visited beautiful places and in rather challenging wind and sea conditions, which only an expert sailor could make so pleasant!

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