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

Greece:

Cyclades

Duration:

7 days - 6 nights

Max number of passengers:

6 people

Available:

September

Suitable for travellers:

20 - 60 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

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 certified professionalboat. 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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18+

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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: 5:00 PM

Our trip ends here:

Santorini Harbour.

Check-out: 5:00 PM

Leg 1

Day 1 Welcome aboard!

Boarding from 17.00 in Kos Town. Accommodation in the welcome aperitif cabin. Free evening.

Day 1 Welcome aboard!

Leg 2

Giorno 2 Pserimos e Kalymnos

Departure with a nice upwind to reach Pserimos, one of the very few islands of the Dodecanese with sandy beaches. After lunch, a sail awaits us along the west coast of Kalymnos, the mythical island of sponge fishermen, today a paradise for climbers due to the presence of mountains and rock walls overlooking the sea. Night in Telendos or in the small bay of Emborios.

Giorno 2 Pserimos e Kalymnos

Leg 3

Day 3 Levitha

Departure for the very small island inhabited only by a family whose three generations manage the only restaurant they supply with 0 km products from the farm they own. Day in the bay at anchor in complete relaxation and a short walk to go up to the characteristic restaurant.

Day 3 Levitha

Leg 4

Day 4 Amorgos

Early morning departure for Amorgos. Sailing to Amorgos is a journey into the essence of the Cyclades. We will spend the afternoon enjoying some relaxation and well-deserved rest after the crossing. Night at anchor.

Day 4 Amorgos

Leg 5

Day 5 Amorgos again

Arrive at the port of Katapola where we will go ashore to visit the Monastery of Panagia Hozoviotissa. Perched on a steep cliff 300 meters above the sea, it is one of the most spectacular in Greece. In the evening we will have dinner in a tavern along the narrow cobbled streets of Chora.

Day 5 Amorgos again

Leg 6

Day 6 Ios

Route to Ios to reach the beautiful and quiet Bay of Manganari where we will spend a relaxing day at sea with dinner on the boat and night at anchor.

Day 6 Ios

Leg 7

Day 7 Santorini

Departure for Santorini. We'll sail through the caldera of the volcano, admiring the spectacular views. Arrival in the south of the island in the Red Beach for disembarkation at 5 pm (here buses to the city also depart).

Day 7 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.

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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