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DODECANESO SECRET: Kalymnos and micro-islands with skipper and kitchen

Greece:

Dodecanese

Duration:

6 days - 6 nights

Max number of passengers:

6 people

Available:

-

Suitable for travellers:

18 - 70 years

Boarding from:

Kos Town

What's included

Cancellation policy

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Super!

Organised by:

Emanuel & Annalisa

Member since 2016 -

Organisation

Italian

English

German

Spanish

French

This experience, in a nutshell

Our Secret Dodecanese


We are Annalisa and Emanuel, a couple of skippers who spend six months of the year in the Dodecanese, an archipelago of over 163 islands and islets where the beauty of unspoilt nature blends with the richness of Greek culture. Our itineraries are called 'Secret Dodecanese' because they are born out of a love for these islands and a desire to share their most beautiful and hidden treasures with our guests.


The Voyage


Spurred by the meltemi that blows constantly here, we will sail to discover the islands, dropping anchor in enchanting bays with cobalt blue, turquoise and aquamarine waters where we can take long swims. We will see ancient fortresses and castles, kores from which to admire breathtaking views and small white churches perched atop impossible cliffs. In the evening, we will greet the sun with a toast and sleep at anchor, under the stars, or in characteristic village harbours. And, accompanying us, always the smile of the Greeks, 'una fazza una razza', because travelling is also about meeting people and finding friends.


Life on board


Boating is synonymous with freedom, so ours are always proposals and everyone is free to choose how to spend their time. On board you can participate in the running of the boat, sunbathing, reading, chatting. There are flippers and masks for snorkelling and a tender with an outboard motor to reach the beaches or to go ashore and explore the islands. We take care of the preparation of meals on the boat, because in addition to our passion for the sea and sailing, we also like to cook. If anyone shares this passion, they are welcome in the kitchen! Cooking, on the other hand, is a team game, everyone plays their part. Sometimes we dine ashore in typical taverns where we enjoy the cuisine of the Dodecanese, a treasure trove of Mediterranean flavours with Middle Eastern influences from neighbouring Turkey.


Itinerary


With the sky always clear and the wind blowing the sails, we will explore the islands on our itinerary. It will be the wind and the sea that will show us the best route to follow. With 25-30 knots of wind upwind or downwind, sailing is a pleasure; if upwind, sailing can become challenging, so the routes are always at the discretion of the skippers who are responsible for the well-being and safety of the crew. And, anyway, often the best things happen when they are not planned.


No Departures available

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13+

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Boat & Classes of Service

Dufour 455 Grand Large - 2006

Type

Sailboat

Length

13.75 m.

Toilets

3

Cabins

4

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10+

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Our itinerary

Our trip starts here:

Kos Town.

Check-in: 8:00 AM

Our trip ends here:

Kardamena.

Check-out: 9:00 AM

Leg 1

Saturday: Pserimos and Plati

Depart Kos Town to Pserimos, one of the very few islands in the Dodecanese with sandy beaches. Very small and with less than 50 inhabitants, it is full of bays with crystal clear waters where we will stop for swimming and lunch. A short sail will take us to the island of Plati, a concentration of Caribbean waters in a few square meters of rock and sand where you can take beautiful baths and explore the architectural and natural beauties. Arrival in Vathy, on the island of Kalymnos where we will spend the night.


 


Saturday: Pserimos and Plati

Leg 2

Sunday: East Kalymnos

We will sail along the east coast of the mythical island of sponge divers, today a paradise for climbers due to the presence of mountains and rock walls overlooking the sea. The island is a succession of fjords and small solitary bays where we will stop to immerse ourselves in the waters of all shades of blue and green. The final destination of the day is the Palionisos fjord where we will sleep at the buoy with dinner at the restaurant overlooking the bay.


Sunday: East Kalymnos

Leg 3

Monday: West Kalymnos

We will continue upwind towards the northern tip of the island, stopping along the way at one of the most beautiful bays in Kalymnos where we can snorkel, sunbathe on the white pebble beach and climb the mountain to enjoy the magnificent view of the bay. We will continue sailing on the west side until we reach the Bay of Emborios where more swims, a walk in the nearby village and a night at anchor under the stars await us.


Monday: West Kalymnos

Leg 4

Tuesday: Telendos and Nera

In the morning we will

set sail for Telendos, a very small island with very high rocks overlooking the sea, breathtaking views and beaches that we will reach after a nice walk in the Mediterranean scrub among the archaeological ruins. We'll continue to the island's capital, Pothia, for supplies and a short visit to the village. We will continue to Nera, a private micro-island inhabited only by Stavros and Evangelia who give us permission to moor at their home. Beautiful backdrops and a wonderful view of the sunset await us after a short walk at the top of the hill. Night at anchor.


Tuesday: Telendos and Nera

Leg 5

Wednesday: South Kos

A nice sail at a downwind will take us to Agios Stefanos, south of Kos, where we will stop for swimming and a visit to the small church on the water. We'll continue sailing to Yali for another swim in the Caribbean waters and end our day at the small port of Paloi on Nysiros Island where we'll have dinner and spend the night.


Wednesday: South Kos

Leg 6

Thursday: Pergousa and Yali

Departure for nearby Pergousa and Yali, the white island of pumice. A day dedicated to swimming and snorkeling in the crystal clear waters of the uninhabited islets. Return to Yali for a toast at sunset by the sea and last night at anchor.


Thursday: Pergousa and Yali

Leg 7

Friday: Return to Kos

Morning sail back to the small port of Kardamena south of Kos (near the airport) and disembarkation.


Friday: Return to Kos

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:

Emanuel & Annalisa

Member since 2016 -

Organisation

Italian

English

German

Spanish

French

5.0/5

out of

46

reviews

Skipper

Boat

Destination

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Secret Aegean with skipper and kitchen on board from Kos to Rhodes

07/12/2025

Attilio A.

-

Italy

Excellent welcome, well-designed itinerary, excellent on-board cuisine.
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Secret Aegean with skipper and kitchen on board from Santorini to Kos

06/26/2025

Melissa C.

-

Italy

A week on a sailing boat between Santorini, Anafi, Astypalea, Nisyros and Kos – a real holiday, one of those that stay with you. Annalisa and Emmanuel, our skippers, were incredible: super prepared, but also welcoming and easy-going. They treated us like kings and queens from day one, with a care and kindness that is rarely found. Even when the wind gave us a longer stop on an island, they were able to turn everything into an opportunity to discover beautiful places, have new experiences and eat in authentic places where you spend little and really eat like a god. Even on board you can eat very well: they cook everything themselves, with fresh local products, and you can see that they put passion into it. They are not only good skippers, they are also excellent cooks! Every meal was delicious! We did everything: trekking, bathing in hot springs, visiting the caldera of a volcano, and often slept in quiet and isolated bays, under a sky full of stars. An incredible peace. We almost always sail making us participate in the maneuvers and explain everything to us with patience and passion. It's not your average all-inclusive holiday, it's a different, more authentic and free experience – and that's why it's special. It is real sea, nature, freedom, simplicity. If you are looking for something authentic, away from the chaos and full of beauty, I highly recommend it.
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Secret Aegean with skipper and kitchen on board from Santorini to Kos

06/24/2025

gina c.

-

United States

The skippers are experienced sailors who care about safety + weather conditions and maintain a very clean, comfortable boat down to the smallest details. They were kind enough to help me maneuver a heavy piece of luggage which I'm super grateful for. I booked solo and extremely last minute without knowing the right questions to ask, and I do recommend conversing prior to get a feel of fit for this type of trip. I could have benefited from discussing my dietary preferences and restrictions in comparison to the group, especially given that the food is purchased and prepared by the skippers without the option of purchasing/ cooking your own. It also didn't occur to me to inquire about allotted water consumption per passenger, and in our case a swift shower wasn't possible each day whether on board or in marina. If you decide to embark, know that you are in experienced hands who will carefully anticipate weather restrictions and modify as needed, and you definitely won't be shopping or cooking. Thank you!
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SECRET DODECANESE: Astypalea and Tylos with skipper and kitchen

10/1/2024

Luca Alfonso M.

-

Italy

Emanuel and Annalisa nothing short of fantastic, really exquisite people Very good skippers and fabulous cooks Fantastic and unforgettable holiday

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