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Secret Aegean with skipper and kitchen on board from Kalymnos to Samos

Greece:

Dodecanese

Duration:

7 days - 6 nights

Max number of passengers:

6 people

Available:

-

Suitable for travellers:

20 - 60 years

Boarding from:

Kalymnos

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

We are Annalisa and Emanuel, a couple of skippers who live six months a year in Greece, sailing in the Aegean. We take turns in all roles: boat management, on-board cooking and organization of activities. We like to go to sea and share this passion with people who want to experience the sea in freedom and learn about traditions, landscapes and places that make the Aegean a unique and perfect place to be discovered on a sailboat.


Our routes will take you to discover the most fascinating islands of this sea: from the authentic face of the Dodecanese to the wild nature of the Southern Sporades, passing through the iconic Cyclades and the hidden gems of the Small Cyclades. Each journey begins on one island and ends on another, both connected by direct flights to numerous departure airports. This formula gives you a freer and more complete experience, overcoming the restrictions of loop routes. You will be able to fully enjoy the magic of the trip, without ever retracing your steps, whether you decide to take two consecutive weeks on a boat, or whether you choose to explore the departure or arrival island by land.

 

We will sail far and wide to discover the most beautiful islands with a perfectly equipped, safe and professionally certified boat. Fast crosswind, downwind and upwind edges await us to climb the Meltemi, the typical summer wind of Greece. Those who wish can participate in the maneuvers and steering of the boat, or simply enjoy the moment, the sun and the wind. Each route is designed to mix the pleasure of sailing with moments of adventure and relaxation: snorkeling in the crystal clear waters, trekking along the natural paths to discover breathtaking views, aperitifs by the sea, without forgetting the pleasures of the table to share on board or in picturesque taverns.

No Departures available

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12+

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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:

Kalymnos.

Check-in: 5:00 PM

Our trip ends here:

Pythagóreio.

Check-out: 5:00 PM

Leg 1

Day 1 Welcome aboard!

Boarding in the port of Pothia, Kalymnos, (easily accessible from Kos by ferry) from 17.00. Accommodation in the cabin and welcome aperitif. Free evening.

Day 1 Welcome aboard!

Leg 2

Giorno 2 Kalymnos

Sailing upwind along the east coast of the sponge fishermen's island, today a paradise for climbers from all over the world who come to climb the rock walls overlooking the sea. The landscape is a succession of fjords and small solitary bays where you can swim in all shades of blue and green. Night at anchor or buoy depending on weather conditions.

Giorno 2 Kalymnos

Leg 3

Day 3 Leros

Sail upwind towards the most authentic and everyday of the Dodecanese islands. Stop for swimming in a beautiful bay and then we will continue to the islet of Arkangelos for more swimming and aperitif at sunset. Night at anchor.

Day 3 Leros

Leg 4

Day 4 Macronisi and Lipsi

Departure for Micronisi and Macronisi, two mini-islets with beautiful seabeds. Rock dives and dives followed by lunch. In the early afternoon, head to Lipsi, famous for the beauty of its beaches and the almost lush hinterland, dotted with churches, Mediterranean scrub and cultivated fields. We will sleep at anchor in one of the beautiful protected bays with the possibility of dining on the boat or in a characteristic restaurant.

Day 4 Macronisi and Lipsi

Leg 5

Day 5: Arkoi and Maratho

Short stop in the port of Lipsi to visit the town and refuel and then a nice sail to the small archipelago full of coves with beautiful colors. We'll drop anchor in the turquoise lagoon for a day of swimming. Night at anchor with dinner on the boat or at the restaurant in Maratho or Arkoi, depending on the availability of moorings.

Day 5: Arkoi and Maratho

Leg 6

Day 6 Agathonisi

Route to the very small island that offers us crystal clear waters, authentic villages and unspoiled nature, far from mass tourism. We will anchor in the port of Agios Giorgos with the possibility of dining on the boat or in one of the traditional cuisine restaurants on land.

Day 6 Agathonisi

Leg 7

Day 7 Samos

Early morning sail to Samos and arrival in the beautiful bay of Tsopela for lunch and swimming. In the afternoon we will head to the port of Pythagorion for disembarkation by 17.00.

Day 7 Samos

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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