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

Greece:

Cyclades

Duration:

6 days - 6 nights

Max number of spots:

6

Available:

September

Suitable for travellers:

18 - 60 years

Boarding from:

Milos

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, 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.

€750

6 days - 6 nights

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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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7+

Show all

Our itinerary

Our trip starts here:

Milos.

Check-in: 11:00 AM

Our trip ends here:

Tourlos (Mykonos).

Check-out: 12:00 PM

Leg 1

Milos Adamantas-Kleftiko 14 mn

You set sail from the port of Adamantas and sail along the west coast of Milos to Kleftiko, one of the most iconic places in Greece. Sea caves, natural arches and turquoise water become the stage of the first day. Swimming, snorkeling and total relaxation. Night at anchor, under the white walls illuminated by the moon (we hope there is).

Milos Adamantas-Kleftiko 14 mn

Leg 2

Kleftiko-Kimolos 17 mn

Route to Kimolos, a cozy and authentic island. Anchorage in one of its most beautiful bays, such as Prassa or Bonatsa, with very clear sand and turquoise sea. Afternoon at the beach and quiet evening at anchor.

Kleftiko-Kimolos 17 mn

Leg 3

Kimolos-Sifnos 12 mn

Short sail to Sifnos. Stop for swimming in iconic bays such as Apokofto or Faros, at the foot of the Chrisopigi monastery: clear sea, essential landscape, suspended atmosphere. Depending on the weather, night at anchor in front of Vathi, a small fishing village by the sea or Kamares, the main port, where we will have dinner in a traditional tavern

Kimolos-Sifnos 12 mn

Leg 4

Sifnos-Serifos 16 mn

Continue towards Serifos, a rugged and bright island. Anchorage in the area of Livadi or in a nearby bay such as Psili Ammos. Those who wish can go up to Chora to admire one of the most beautiful views of the Cyclades at sunset. Night at anchor.

Sifnos-Serifos 16 mn

Leg 5

Serifos-Syros 25 nm

Longest crossing of the route to Syros. A day at the beach on the west coast, in quiet bays such as Finikas or Galissas from which to enjoy a beautiful view of the sunset. Night at anchor

Serifos-Syros 25 nm

Leg 6

Syros-Rineia 22 mn

Last great sail to Rineia, an uninhabited island in front of Mykonos. Here time stops: transparent water, absolute silence, no construction. Long swims, dinner on board and starry sky for our last night at anchor.

Syros-Rineia 22 mn

Leg 7

Rineia-Mikonos 10 mn

Our journey ends: six islands, six nights almost always in the roadstead and the boat as the only fixed point in our sea. A short sail will take us to the port of Tourlos Marina in Mykonos for disembarkation. A visit to the sacred island of Delos is highly recommended.

Rineia-Mikonos 10 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

English

German

Spanish

French

5.0/5

out of

55

reviews

Skipper

Boat

Destination

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

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

06/24/2026

Cristina B.

-

IT

My first holiday with the wind, the real one. Constant 22 knots whizzed through the waves. Exciting! Then in the sheltered bays an indescribable turquoise sea awaited us. Top holiday

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