header cover
logo

Log in

Mykonos and the Western Cyclades by sail, with skipper and on-board kitchen

Greece:

Cyclades

Duration:

6 days - 6 nights

Max number of spots:

6

Available:

-

Suitable for travellers:

18 - 60 years

Boarding from:

Tourlos (Mykonos)

What's included

Cancellation policy

avatar image

Super!

Organised by:

Emanuel & Annalisa

Member since 2016 -

Organisation

Italian

French

Spanish

German

English

This experience, in a nutshell

We are Annalisa and Emanuel, experienced skippers and life and travel partners. For six months a year we sail in the Aegean islands, welcoming on board those who want to experience the sea in an immersive way. We love to combine the pleasure of sailing and boat life with the exploration of places, history and local customs, to capture the most authentic essence of Greece. Every year we change route and islands, but the philosophy remains the same: wind in the sails, secluded anchorages and a cuisine prepared with care and imagination, to share with our guests. In summer 2026 we will sail in some of the most fascinating areas of Greece, the Saronic Gulf and the Cyclades islands.

No Departures available

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

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

7+

Show all

Our itinerary

Our trip starts here:

Tourlos (Mykonos).

Check-in: 11:00 AM

Our trip ends here:

Tourlos (Mykonos).

Check-out: 12:00 PM

Leg 1

Mykonos - Rineia 10 mn

After settling into the cabin in Mykonos, we set sail for Rineia, an uninhabited and wild island, ideal for getting into the rhythm of the holiday right away. Swimming, relaxation and lunch on board give the feeling of being away from everything. The first night is spent in the roadstead, a perfect start before heading to more animated islands.

Mykonos - Rineia 10 mn

Leg 2

Rineia - Syros 18 mn

Sail to the south coast of Syros to spend a day at sea in the roadstead. For those who wish, the bus from the Bay of Vari takes you to the city of Hermopolis, the capital of the Cyclades, interesting for its neoclassical architecture and the evidence of the industrial past.

Rineia - Syros 18 mn

Leg 3

Syros - Kythnos 24 nm

Arrival in Loutra: a small village by the sea, known for its natural thermal springs, used since ancient times, where the hot and mineral water gives a moment of true relaxation. The marina is quiet and welcoming, ideal for a walk along the seafront and a dinner in the tavern. A day that combines sea and well-being, without haste.

Syros - Kythnos 24 nm

Leg 4

Kythnos 7 mn

Sail along the beautiful east coast of Kythnos with frequent stops for swimming and snorkeling. Night at anchor.

Kythnos 7 mn

Leg 5

Kythnos - Syros 24 mn

Return to Syros, this time on the west coast, very different from the south: more open, wild and suggestive, with spectacular sunsets over the sea. A complementary stop to the previous one, which allows you to discover another face of the island. Night at anchor

Kythnos - Syros 24 mn

Leg 6

Syros - Rineia 24 mn

Navigation to the islet of Didimi in front of Hermopolis and then course for Rineia. Last swims in crystal clear waters and evening in total tranquility, immersed in the Cycladic silence.

Syros - Rineia 24 mn

Leg 7

Rineia-Mykonos 8 mn

Return navigation to Mykonos and disembarkation. The journey ends with the feeling of having experienced many holidays in one: different islands, changing rhythms, landscapes that remain etched in your mind. And with one more certainty: Greece on a sailing boat does not end here.

Rineia-Mykonos 8 mn

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.

What's included in the price

Boat equipment and facilities

    Final cleaning

    Tender and outboard

    Bedding kit

    Towels kit

Meals and beverages

    Purchase and storage of the galley

    Preparation of meals and drinks

Onboard staff

    Skipper

    Chef

Taxes, fees and moorings

    Visitor or navigation taxes

What you'll have to pay during the experience

Below are the additional expenses you will incur during the experience.

Common Fund

€200 - €250 Per person

Expenses are based on a crew of 6. The amount indicated normally covers the galley for all breakfasts, lunches and dinners and 2/3 outings to the tavern. Alcohol is counted individually, but is usually within the max.

    Galley

    Food for the skipper

    Food for the crew

    Mooring fees

    Embarkation and disembarkation mooring fees

    Fuel (boat/tender)

What's NOT included in the price

Below are the services that are not included in the price of the experience, including any available optional services that you may pay directly to the organiser (we advise you to inform the organiser prior to departure in case you wish to purchase such services and arrange the payment terms directly with him).

Excluded

    Meals/drinks consumed ashore

    Alcoholic drinks

    Transfers from/to the airport

    Flights or Transfers from/to the destination

    Museum/park/places of worship admissions

    Trainer

Frequent questions

The organiser reviews

avatar image

Super!

Organised by:

Emanuel & Annalisa

Member since 2016 -

Organisation

Italian

French

Spanish

German

English

5.0/5

out of

56

reviews

Skipper

Boat

Destination

avatar image

From Mykonos to Athens by sail, with skipper and on-board kitchen

10/7/2026

manuela c.

-

IT

Annalisa and Emanuel were professional and nice, we unfortunately had the worst week of wind in sailor's memory and we were forced to always stay still without sailing except for 3 hours on the first day so I can't talk about the cruise destinations except for syros that they propose and that, unlike other islands, it is not crowded and therefore maintains something of the Greek spirit with beautiful villages and has beautiful trekking and beaches (the beaches unfortunately due to wind were not frequentable but I saw them in the treks). Beautiful and spotless boat absolutely comfortable. What can I say? Hope to see you again next year! Maybe with better luck for the climate! Thank you

From Milos to Mykonos by sail, with skipper and on-board kitchen

08/13/2026

Aurora G.

-

IT

It was the first experience on a boat... unique and spectacular! Annalisa and Emanuel were able to make us feel immediately at ease. Both, experienced and close-knit sailors, emanate an immense passion for what they do, able to transmit it to all their companions. Two sunny, kind, helpful and knowledgeable people who take you to discover fantastic and exclusive places; deserted beaches and islands, far from the chaos, where it is possible to admire all the beauty of the Greek islands both during the day and during the night with breathtaking starry skies. The boat is well organized, allowing you to move freely and safely even in small spaces. Moreover, Annalisa and Emanuel are also fantastic cooks, capable of preparing exquisite delicacies with local flavors and in great abundance! Also thanks to our travel companions, we can say that we embarked as perfect strangers and then disembarked feeling part of a group of friends. Thank you very much Emanuel and Annalisa for this unforgettable experience... See you soon!
avatar image

From Milos to Mykonos by sail, with skipper and on-board kitchen

08/11/2026

Anna M.

-

IT

First experience on a sailing boat, it far exceeded my expectations! Emanuel & Annalisa are fantastic: they steer the boat with great safety, even when the weather conditions are not always easy due to the Meltemi and they know how to find sheltered bays where they can enjoy the wonderful Greek sea and breathtaking landscapes, far from the typical crowds of August. They cooked delicious dishes for us, making us discover and taste many local ingredients and flavors. The boat is well organized and equipped with everything you need to spend a pleasant and relaxing week. It is definitely not a holiday for everyone: it requires flexibility, a spirit of adaptation and the desire to share spaces and experiences. But once you try it, it is a type of holiday that remains in the heart. Hop on as a guest and come down as a friend! Thank you very much Annalisa & Emanuel, and fair winds!

From Piraeus to Mykonos: the Aegean by sail, with skipper and on-board kitchen

06/24/2026

Cesare S.

-

IT

Annalisa and Emanuel were fantastic hosts! They made us sail and cooked us excellent meals making us spend a beautiful week discovering the sea of the Cyclades and its beautiful bays, despite the Meltemi

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

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