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Sailing holiday in the Cyclades: fast sailing and gourmet cuisine

Greece:

Cyclades

Duration:

6 days - 7 nights

Max number of passengers:

6 people

Available:

-

Suitable for travellers:

18 - 70 years

Boarding from:

Mykonos

What's included

Cancellation policy

avatar image

Super!

Organised by:

Lorenzo & Annalisa

Member since 2013 -

Organisation

Italian

English

French

This experience, in a nutshell

An unforgettable sailing adventure from Mykonos to Milos in the heart of the Cyclades, led by two experienced Italian skippers. Not only will you sail among the beautiful islands of the northern Cyclades, but you will experience a unique journey, enriched by the fine Italian cuisine served on board, all wrapped in the magic of the Aegean Sea.


The boat, designed to combine comfort and performance, will allow you to sail quickly and safely from one island to another. You will feel the adrenaline of speed, without ever giving up relaxation and the pleasure of experiencing the sea in total comfort.


Your adventure starts from iconic Mykonos, with direct flights from Italy, it is the ideal starting point for your holiday. From Mykonos and its sparkling tourism we escape and discover the island of Rineia, a hidden gem to be discovered. This wild and uninhabited island will welcome you with pristine beaches and crystal clear waters.


A short walk from Rineia, you will find Delos, one of the most important archaeological sites in Greece, a UNESCO World Heritage Site. It is a real journey back in time, a cultural experience that will leave you enchanted. Continuing our route, we will arrive in Syros, the island that combines history and modernity. The beating heart of the island, Hermopolis, is the capital of the Cyclades Islands. With its neoclassical buildings, theaters and squares that recall its glorious maritime past.


After an exciting sail, we'll land in Serifos, an island with an authentic and relaxed atmosphere. Its Chora, perched on top of a hill, will amaze you with its white houses and panoramic views of the sea. The next stop takes us to Sifnos. In Sifnos, we'll stop at one of its most beautiful bays, a pirate hideout, where you can swim in turquoise waters and relax in the sun. In a crescendo of isolated and wonderful bays with the wind in our sails we sail fast to Polyaigos, one of the wildest and most unspoiled islands of the Cyclades. A true natural paradise, Polyaigos is famous for its crystal clear waters, which fade from turquoise to deep blue, and its hidden caves, the rocky walls veined with colors that change as the sun goes down. A total oasis of peace, perfect for snorkeling or simply admiring the breathtaking landscape.


An exciting sail takes us to Milos. One of the most spectacular islands in the Aegean Sea, it will amaze you with its volcanic formations, white sandy beaches and secret coves that can only be reached by sea. The island is a mix of lunar landscapes and traditional villages.

Get ready to sail the foaming waves, driven by a vigorous wind, aboard a fast and high-performance boat.



This sailing holiday is much more than just a cruise: it is an immersion in the breathtaking beauty of the Greek islands, in their fascinating history and in the authentic flavors of the Mediterranean and thanks to the hospitality and experience of your skippers it will remain forever in the heart.

No Departures available

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14+

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Boat & Classes of Service

43 - 2010

Type

Sailboat

Length

13 m.

Toilets

2

Cabins

3

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11+

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Our itinerary

Our trip starts here:

Mykonos.

Check-in: 6:00 PM

Our trip ends here:

Milos Harbour.

Check-out: 9:00 AM

Leg 1

Imbarco a Mykonos

First day of sailing holiday

Start your enchanting sailing holiday by boarding in the heart of the Cyclades, Mykonos. We will welcome you on board in the late afternoon and introduce you to what will be your home for the week ahead.

As soon as all guests are accommodated in their respective cabins, we will hoist the sails towards a quiet bay, away from the chaotic nightlife of Mykonos. Here, the atmosphere becomes magical: while the reflections of the sunset dance on the water, your skippers will turn into real cooks, preparing a delicious dinner. Enjoy your first evening at sea under a sky quilted with stars, then let yourself be lulled by the waves on your first night on the boat.

Leg 2

The Priceless Value of Delos

Second day of sailing holiday

With the crisp Aegean wind filling the sails, after a nutritious morning meal on board, a short and leisurely sail will take you to the sacred island of Delos. Delos is an archaeological site of inestimable value and was in ancient times the most famous and the most sacred of all the islands, considered the mythical cradle of Apollo and Artemis.

In the afternoon, your adventure continues to Rineia, a quiet and lesser-known sister island only a short stretch of sea away.

An aperitif in the cockpit of the boat watching the sunset bathing the landscape in a golden light and then dinner will be prepared and served on board by your skippers. The pleasure of good food and the company of your new friends.

The silence of Rineia is the ideal companion for an evening of rest, the effervescence of the renowned Mykonos can be perceived in the distance with the glow of its lights.

Leg 3

Wind in the Sails towards Syros

Your third day at sea becomes an exciting experience while our boat, taking advantage of a lively wide upwind (if the wind is the prevailing one) launches into a navigation that will delight sailing enthusiasts. It is the ideal day for those who have the desire to learn, with the opportunity to try their hand at maneuvering or take the helm and feel the true essence of the sea.

The fast sail culminates with the arrival in a serene and welcoming anchorage.

The lively and colorful port of Hermopolis awaits you in the afternoon. Explore the city of Hermopolis, the main center of Syros and the capital of the Cyclades. Admire its neoclassical architecture and get lost in the narrow streets vibrant with history and culture.

Leg 4

Sailing to Serifos

Leaving the bustling capital of Syros behind, we'll sail along the southern coast of the island, and then cross the majestic Aegean Sea channel, where the cobalt blue of the sea is lost on the horizon. Our destination is the picturesque Serifos.

If you wish, you can actively participate in the maneuvers on board, a unique opportunity to acquire navigation notions, or enjoy the pleasure of admiring the panorama that opens up in front of you.

We anchor in front of a postcard-perfect golden beach, where the crystal clear sea invites you to dive. After lunch, the sea will be our playground: you can relax with a regenerating swim or explore the seabed with snorkeling.

In the late afternoon we will land in the beautiful bay of Livadi. From here, a pleasant walk will lead us to the Chora of Serifos, the old village perched on top of the hill. From here the view of the surrounding islands with the light of the sunset is spectacular.

Leg 5

Sailing to Sifnos

The day begins with the bow of the boat heading towards Sifnos: we hoist the sails and, with the wind in our sails, our boat glides fast over the foaming water of the Aegean Sea. The pace of sailing is dynamic and adventurous, perfect for those looking for thrills during a sailing holiday.

We skirt the east coast of Sifnos, admiring the wild and authentic landscape of the island. The first stop is in an isolated and unspoiled bay, accessible only by sea, a true corner of paradise, surrounded only by the sound of the waves and the scent of the sea.

After a delicious lunch prepared on board, we continue our navigation towards a second cove that looks like something out of a pirate tale.

The evening ends with a gourmet dinner prepared by your skippers, while the sky above us lights up with stars. Far from light pollution, we find ourselves observing the starry sky, a magical moment that only a sailing holiday can offer.

Leg 6

Polyaigos: paradiso naturale

Start the day in the best way: a refreshing dip as soon as you wake up, immersed in the crystal clear waters that surround the boat. After a regenerating breakfast, we hoist the sails and let ourselves be carried away by the wind in our sails, sailing towards the beautiful island of Polyaigos, one of the wildest and most unspoiled of the Cyclades.

Our destination for the evening is the Bay of Faros, a natural wonder that looks like something out of a postcard, with the sea going from deep blue to emerald green. The beach, which is often deserted, offers a perfect retreat for relaxing, sunbathing and swimming in transparent waters.

For the more active, a beautiful sunset excursion to the lighthouse overlooking the bay offers an incredible panorama.

The evening ends with a gourmet dinner prepared by your skippers, under a sky quilted with stars. Away from light pollution, we can enjoy the spectacle of the Milky Way unveiling itself in all its magnificence.

Leg 7

Milos: volcanic contrasts

With the sun rising on the horizon, we hoist the sails and point the bow towards the magnificent island of Milos. Famous for its volcanic landscapes and spectacular beaches, Milos is the perfect grand finale to this trip.

If the wind conditions are favorable, we'll stop at Sarakiniko, one of the most iconic beaches in Greece. The white cliffs, sculpted over time by wind and waves, create a lunar landscape that seems to belong to another world.

In the early afternoon, we will arrive in Adamas, the main port of Milos.

One of the most magical moments of the day will certainly be the sunset, which you can admire from the top of the Monastery of Profitis Ilias. From here, the panoramic view of Milos and the sea at sunset is an experience that will leave you spellbound.

The day will end with dinner in Plaka, the ancient village of the island, a walk through its delightful cobbled alleys.

Leg 8

See you next time

Here we are at the end of our journey. Before disembarking, we want to thank you for sharing this adventure with us among the unspoiled beauty of the Greek islands. As your feet touch the ground, we are sure that you will take with you the memory of an authentic and unforgettable experience. A sailing trip that is not just a holiday, but a total immersion in nature and the sea, which will entice you to come back to experience even more new emotions. A unique way to unplug from the lightning-fast city life.

See you soon, for another adventure in the waves!

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:

Lorenzo & Annalisa

Member since 2013 -

Organisation

Italian

English

French

4.9/5

out of

41

reviews

Skipper

Boat

Destination

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Fast sailing holiday in the Cyclades with gourmet cuisine on board

06/15/2025

Alberto L.

-

Italy

Un Sogno a Vela Indimenticabile con Lorenzo e Annalisa Se cercate un'esperienza in barca a vela perfetta tra le Cicladi, scegliete Lorenzo e Annalisa. Per una settimana, ci hanno guidato da Lavrio a Mykonos, esplorando le Piccole Cicladi, e siamo rimasti entusiasti. La loro conoscenza delle isole è eccezionale, permettendoci di scoprire angoli di paradiso e condizioni di navigazione ideali. A bordo, l'atmosfera è sempre stata rilassata e accogliente. Da segnalare la cucina veramente deliziosa e variegata!! . La loro sinergia crea un ambiente sereno e piacevole. Le Piccole Cicladi ci hanno regalato paesaggi mozzafiato, e grazie a loro abbiamo vissuto appieno ogni momento: bagni in baie deserte e cene in taverne tipiche. Lorenzo e Annalisa sono compagni di viaggio appassionati ed esperti. Hanno superato ogni aspettativa, trasformando una vacanza in un'avventura straordinaria. Li raccomandiamo vivamente a chiunque desideri un'esperienza autentica e indimenticabile tra le isole greche.
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Small Cyclades

09/14/2024

Stefan E.

-

Switzerland

Annalisa and Lorenzo are wonderful hosts and very skillful skippers. We had an amazing time with delicious food, visiting beautiful spots, swimming at peaceful hidden islands. The whole planning is flawless, given us a very relaxing trip and memorable first sailing experience. Grazie mille =D
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Small Cyclades

08/26/2024

EMANUELE P.

-

Italy

Tutto perfetto! Annalisa e Lorenzo sono bravissimi ed offrono un servizio unico. Assolutamente da provare!
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Small Cyclades

08/17/2024

Márcio R.

-

Italy

Lorenzo and Annalisa are fantastic, very experienced and know the conditions of the region well. From the first moment I felt at ease, each meal was very tasty and prepared with great care. It was my first trip of many to come!

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