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SECRET DODECANESE: Astypalea and Tylos 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:

Kardamena

What's included

Cancellation policy

avatar image

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 a year in the Dodecanese, an archipelago of over 163 islands and islets where the beauty of unspoiled nature blends with the richness of Greek culture. Our itineraries are called "Secret Dodecanese" because they are born from the love for these islands and the desire to share their most beautiful and hidden treasures with our guests.



The journey


On the wings of the wind we will sail in the mythical Aegean, to reach Astypalea, the famous butterfly island, and small lesser-known islands of striking beauty. This is the itinerary with the longest navigation, suitable for those who want to have a real sailing experience, with the wind upwind/crosswind that always blows cheerfully here. The islands that await us are among the most beautiful in the Aegean, to be explored by boat, to swim in the small bays between high rocky promontories or enjoy the fine sandy beaches, but also to be explored on foot, to take in breathtaking views from the top of the mountains or the Chore with the characteristic whitewashed houses.



Life on board


Barca is synonymous with freedom, so ours are always offered and everyone is free to choose how to spend their time. On board you can participate in the management of the boat, sunbathe, read, chat. There are fins and masks for snorkeling and a tender with outboard to reach the beaches or to go ashore and explore the hinterland. We take care of the cooking on the boat, because in addition to our passion for the sea and sailing, we also like to be in the kitchen. If anyone shares this passion, they are welcome in the kitchen! Fixing up, on the other hand, is a team game, everyone does their part. Sometimes we will have dinner on land in typical taverns where we can taste the cuisine of the Dodecanese, a treasure trove of Mediterranean flavors with Middle Eastern influences from neighboring Turkey.



Itinerary


With the sky always clear and the wind that fills the sails, we will discover the islands of our itinerary. The wind and the sea will show us the best path to follow. With 25-30 knots of wind in the tails or downwind, sailing is a pleasure; If upwind, sailing can become challenging, therefore, itineraries are always at the discretion of the skippers who are responsible for the well-being and safety of the crew. And, by the way, often the best things happen when they are not planned.

No Departures available

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11+

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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:

Kardamena.

Check-in: 8:00 AM

Our trip ends here:

Kardamena.

Check-out: 9:00 AM

Leg 1

Saturday: South Kos

Departure from Kardamena and route to Agios Stefanos, one of the most beautiful areas of Kos with its calm and crystal clear sea. In front of the long strip of beach stands the islet of Kastri with the monastery of St. Andonios. The custom is to swim at the church, climb the rocks and ring the small bell placed next to the church. On the beach there are also the ruins of ancient Christian basilicas. Night at anchor or at the small port of Kamari.

Saturday: South Kos

Leg 2

Sunday: Astypalea

Departure early in

the morning for a beautiful and long sail with arrival in Astypalea in the early afternoon. Located in the middle of the Aegean, the island is halfway between the Dodecanese and the Cyclades, with which it shares the barren appearance, the windmills, the villages of white houses, the crystal clear waters and the beautiful beaches. In the afternoon, relax with baths in the crystal clear waters of the island in the shape of a butterfly, a model of environmental sustainability. The plan is for the island's entire car fleet to become zero-emission, using only electric vehicles. After public administration and public transport, rental companies and private individuals are also converting to electric. We will sleep at anchor under the stars, surrounded by nature. Anchor at anchor or at the city quay and visit of Chora with dinner at the restaurant.

Sunday: Astypalea

Leg 3

Monday: Koutsomytis and Kounoupa

Two small paradises that can only be reached by boat from Astypalea, after a short navigation. There are many beautiful beaches where you can swim in the water that looks like a natural pool and relax in the sun. Overnight at anchor or return to Astypalea.

Monday: Koutsomytis and Kounoupa

Leg 4

Tuesday: Syrna

Morning departure in the direction of Syrna, a very small uninhabited island without services, with pristine waters, often beaten by the meltemi. If the weather conditions are favorable, we will set you for a quiet day and a night at anchor.

Tuesday: Syrna

Leg 5

Wednesday: South Tylos

Morning departure for Tylos. A natural oasis and geological park, it is the world's first zero-waste island. We will drop anchor in one of the deserted bays with crystal clear seabeds where we will spend the day, completely immersed in nature and away from everything. Either we can sleep in the harbor under the stars, lulled by the waves or look for a place in the small port of the village of Livadia for a dinner at the restaurant.

Wednesday: South Tylos

Leg 6

Thursday: Yali

Depart early in the morning for a beautiful and long sail to the uninhabited island of Yali south of Kos. With its Caribbean waters and white pumice stone beaches, it will be our paradise where we will spend a lazy day at the beach after our long sailings. Aperitif by the sea at sunset, dinner on the boat and night at anchor.

Thursday: 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

45

reviews

Skipper

Boat

Destination

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

06/26/2025

Melissa C.

-

Italy

Settimana in barca a vela tra Santorini, Anafi, Astypalea, Nisyros e Kos – una vacanza vera, di quelle che ti restano addosso. Annalisa ed Emmanuel, i nostri skipper, sono stati incredibili: super preparati, ma anche accoglienti e alla mano. Ci hanno trattati come re e regine fin dal primo giorno, con una cura e una gentilezza che raramente si trovano. Anche quando il vento ci ha regalato una sosta più lunga su un’isola, hanno saputo trasformare tutto in un’occasione per scoprire posti bellissimi, fare esperienze nuove e mangiare in locali autentici dove si spende poco e si mangia davvero da dio. Anche a bordo si mangia benissimo: cucinano tutto loro, con prodotti locali freschi, e si vede che ci mettono passione. Non sono solo bravi skipper, sono anche ottimi cuochi! Ogni pasto era delizioso! Abbiamo fatto di tutto: trekking, bagni nelle sorgenti calde, visita alla caldera di un vulcano, e spesso dormivamo in baie tranquille ed isolate, sotto un cielo pieno di stelle. Una pace incredibile. Si naviga quasi sempre a vela facendoci partecipare alle manovre e spiegandoci tutto con pazienza e passione. Non è la solita vacanza all-inclusive, è un’esperienza diversa, più autentica e libera – e proprio per questo è speciale. È mare vero, natura, libertà, semplicità. Se cercate qualcosa di autentico, lontano dal caos e pieno di bellezza, ve la straconsiglio.
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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 ed Annalisa a dir poco fantastici, persone veramente squisite Bravissimi Skipper e Favolosi cuochi vacanza fantastica ed indimenticabile
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DODECANESO SECRET: Kalymnos and micro-islands with skipper and kitchen

09/1/2024

Inaya V.

-

Australia

If you find yourself able to do this experience I think you’d be considered one of the lucky ones. Thank you beautiful gorgeous Annalisa and Emanuel

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