header cover
sailsquare logo

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

Greece:

Dodecanese

Duration:

7 days - 6 nights

Max number of passengers:

6 people

Available:

July - September

Suitable for travellers:

20 - 67 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

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.

€1,050

7 days - 6 nights

experience image 0experience image 1
experience image 2
experience image 3

19+

Show all

Boat & Classes of Service

Dufour 455 Grand Large - 2006

Type

Sailboat

Length

13.75 m.

Toilets

3

Cabins

4

boat image 0boat image 1
boat image 2
boat image 3

10+

Show all

Our itinerary

Our trip starts here:

Kardamena.

Check-in: 5:00 PM

Our trip ends here:

Rhodes.

Check-out: 5:00 PM

Leg 1

Day 1 Welcome aboard!

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

Day 1 Welcome aboard!

Leg 2

Day 2: Gyali and Nisyros

Heading south to the small, uninhabited island of Gyali. With its Caribbean waters and white pumice stone beaches, it will be our paradise where we will spend a lazy day at the beach. Night at anchor in the bay or in the nearby port of Nisyros with dinner in a tavern.

Day 2: Gyali and Nisyros

Leg 3

Day 3 Tilos

We'll sail along the volcanic island of Nisyros and head for Tilos. A natural oasis and geological park, it is the first zero-waste island in the world. We will anchor in one of the bays north of Livadia, the village overlooking a very long pebble beach, or in the small marina.

Day 3 Tilos

Leg 4

Day 4: Tilos and Chalki

We'll drop anchor in one of the deserted bays of South Tilos where we'll spend the morning, completely immersed in solitary nature. After lunch we head south towards the island of Chalki, the smallest inhabited island of the Dodecanese. Swim stop and then we will look for a mooring in the village, a picturesque port of Venetian origins, with colorful houses in neoclassical style overlooking the transparent sea. Night in port with dinner in the tavern.

Day 4: Tilos and Chalki

Leg 5

Day 5: Alymia and Symi

Departure in the morning for Alymia. The only two inhabitants, Kostas and his wife, have restored an ancient monastery that can now be visited. There are also the ruins of the barracks of the Italian soldiers stationed during the occupation. Alymia offers beautiful backdrops and a lovely backdrop for our breakfast. Departure for Symi west where we will spend the night at anchor.

Day 5: Alymia and Symi

Leg 6

Day 6 Symi

Departure for the east coast with its beautiful bays where we will spend the morning. In the afternoon we will head to Symi Town, with its elegant pastel-colored buildings in Greek neoclassical style, shops, and many places to spend a pleasant evening. Night in the Marina in one of the two ports of the city and dinner in the tavern.

Day 6 Symi

Leg 7

Day 7 Trompetta and Rhodes

A beautiful sail will take us south of Symi for a swim break and lunch in Trompetta, and then route to the beautiful medieval city of Rhodes a UNESCO World Heritage Site. Disembarkation at 17.00 in the Marina of Rhodes.

Day 7 Trompetta and Rhodes

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

avatar image

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.
avatar placeholder

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.
avatar placeholder

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!
avatar image

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

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964