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Fast sailing boat holiday from Mykonos to Santorini with 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

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Super!

Organised by:

Lorenzo & Annalisa

Member since 2013 -

Organisation

English

French

Italian

This experience, in a nutshell

This sailing holiday kicks off in Mykonos, in the heart of the Cyclades. We set sail in the late afternoon to reach a quiet bay. The next day is dedicated to visiting ancient Delos, followed by a relaxing afternoon in the crystal clear waters of Rineia.


Continuing, we leave for Naxos, with a morning among rocks and islets before reaching the cheerful Chora, dominated by the suggestive Portara and the Venetian Kastro.


We then continue with an exciting sailing sail towards Koufunissi, between natural pools and panoramic stops, to finally reach the exploration of the remote bays of Keros, an ideal place to spot dolphins, turtles and, with a little luck, the monk seal.


Taking advantage of a favorable wind, we land in Iraklia, a remote and peaceful island, for a swim in a bay with a wreck visible even from the surface. In the afternoon, head to Ios, where you can enjoy the sunset from its lively Chora. The adventure continues with a trip to explore the island, before sailing to Santorini, where the contrast between the volcanic rock and the white villages on the edge of the caldera gives an amazing view. The evening ends with a dinner on land in the picturesque village of Oia, immersed in the timeless charm of the island.


You will be welcomed on board by two experienced Italian skippers, who will take you not only through some of the most fascinating islands in the Aegean Sea, but will also let you savor delicacies of Italian gourmet cuisine, turning every meal into a gastronomic journey.


Our boat, a fast sailboat, an ocean fast-cruiser, is designed to offer you maximum comfort without sacrificing performance: you will enjoy fast and exciting sailing, accompanied by the sound of the wind filling the sails and the adrenaline of reaching fascinating destinations.

No Departures available

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26+

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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:

Santorini Harbour.

Check-out: 9:00 AM

Leg 1

Start of the adventure in Mykonos

Boarding in Mykonos in the late afternoon, easily reachable thanks to direct flights from Italy. Once on board, after settling into our respective cabins and getting to know the crew, we'll raise anchor to reach a quiet bay, away from the hustle and bustle of the island. Here we will spend the night lulled by the gentle movement of the sea.

The day ends with a dinner on the boat prepared by the skippers, who will delight you with fresh and genuine flavors. A convivial and relaxing moment, perfect for immersing yourself in the unique atmosphere of this sailing holiday.

 

Leg 2

Delos and relax to Rineia

The morning is dedicated to the discovery of the archaeological park of Delos, a place full of charm and history, where you can relive ancient legends and breathe the atmosphere of classical Greece.

After lunch, we set sail for Rineia and drop anchor in a bay with crystal clear water, ideal for relaxing or having fun with activities at sea and on the beach.

The day ends with a dinner on board, followed by an evening spent contemplating the starry sky, in complete harmony with the surrounding nature.

Leg 3

Nice sail to Naxos

The day begins with an exploration of the jagged rocks and islets that line the island of Rineia, a natural paradise to be experienced in total tranquility.

In the afternoon, we let the wind carry us in our sails towards Naxos, the largest of the Cyclades, appreciated for its lively atmosphere and genuine charm.

At nightfall, we enter the streets of Chora, where we are welcomed by the imposing Portara, the majestic door of the temple of Apollo overlooking the sea, perfect for watching a breathtaking sunset. Then, we get lost in the labyrinth of alleys that lead to the Kastro Veneziano, from which we can enjoy a unique view of the port and the city. Along the way, we come across craft shops offering typical products.

The evening is colored with lights and scents in the local taverns, where the Greek cuisine and the hospitality of the inhabitants make the experience even more special.


Leg 4

Tailwind for Koufunissi

The tailwind blows us swiftly over the waves, making the crossing to Koufunissi a thrilling experience as our sailboat glides fast. Along the way, we take a refreshing break in the natural pool of Porì, a taste of the beauty of this amazing island.

A scenic walk invites us to explore the rugged coastline, where delightful beaches and natural pools alternate. Among these, the most famous swimming pool in Koufunissi, the Devil's Eye, stands out, in which taking a bath is a real must.

For those who want to extend the fun, the beach clubs offer the opportunity to enjoy a drink with a view of the picturesque island of Keros, giving a magical and relaxed atmosphere even at nightfall.

Leg 5

Keros: baie sperdute e foche

The day is entirely dedicated to exploring the most remote bays of the uninhabited island of Keros, an authentic treasure hidden in the heart of the Cyclades. During our navigation, we may spot sea turtles, dolphins and, with a bit of luck, even the monk seal. Surrounded by peace and unspoiled nature, we immerse ourselves in this small paradise that has remained unchanged over time.

Leg 6

Bay in Iraklia and the lively Ios

Taking advantage of the breeze on the side, we sail quickly towards the remote Iraklia, an island little traveled by mass tourism, where peace and tranquility reign supreme. In a bay with incredibly clear water, we drop anchor to explore a wreck visible even from the surface, a real underwater treasure that gives a touch of mystery to our stop.

In the early afternoon we set sail again, pointing the bow towards Ios and landing in its lively port. As the sun goes down, we go up to Chora to soak up its crisp evening atmosphere and enjoy spectacular views of the surrounding islands, illuminated by the golden light of sunset. The day ends with a plate of tagliatelle with meat sauce prepared on board, transforming dinner into a moment of authentic conviviality and flavor.

Leg 7

Spectacular Santorini

Before leaving the island we allow ourselves a few hours of exploration from the lively Chora and its liveli. You can go among characteristic windmills and white churches perched between the houses. An unmissable stop is the church of Panagia Gremiotissa, from which you can enjoy a breathtaking view of the sea and the surrounding hills, as well as the suggestive Odysseas Elytis Theater.

After lunch, we hoist the sails and set course for Santorini. Arriving by boat is a unique experience: the contrast between the black rock and the white villages perched on the edge of the caldera, framed by a deep blue sky, offers a surprising glance. We sail in the waters of the submerged crater and stop for a regenerating bath, surrounded by one of the most fascinating scenery in the Aegean.

The sail then continues towards the famous Red Beach, the red beach with an almost surreal atmosphere.

Leg 8

See you in Santorini

After breakfast comes the least pleasant moment of every cruise: the final goodbyes. With a wealth of indelible memories and the promise to see each other again soon, you will leave the boat that accompanied you on this unforgettable adventure, carrying in your heart the smiles, sunsets and emotions experienced together.

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

English

French

Italian

4.9/5

out of

44

reviews

Skipper

Boat

Destination

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Fast cruising Cicladi Occidentali

08/26/2025

Sergio B.

-

Italy

Annalisa and Lorenzo are first and foremost two wonderful people. Then they are two very experienced sailors: they have sailed around the world; they know the waters of the Aegean by heart. Finally, they are also great as cooks: where do you find the barbecue on the boat and the freshly hand-pulled egg pasta below deck? Only from them! The bays where they took us were breathtaking.
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Small Cyclades

08/18/2025

Franesco B.

-

Italy

An exceptional holiday! Challenging sea conditions but two professionals proceeded impeccably. Together we sailed sublimely, overcoming adversity, finding ourselves immersed in a true and uncontaminated reality. Undoubtedly a recommendable holiday but I always suggest doing it with the mentality of those who want to help a companion (not a skipper), of those who want to savor intense and sincere realities forgetting some secondary comforts. Finally, special mention to the culinary skills of Lorenzo and Annalisa. Super
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Fast sailing holiday in the Aegean with gourmet cuisine

07/20/2025

Mercedes S.

-

Spain

It has been a real top 10 experience! Both skippers are incredibly professional and incredible hosts You feel at home as of minute one Awesome and balanced food and very comfortable cabins Postcard and magic spots visited away from crowds Annalisa and Lorenzo are A little treasure just discovered THANK YOU in capital letters! ❤️
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Fast sailing holiday in the Cyclades with gourmet cuisine on board

06/15/2025

Alberto L.

-

Italy

An Unforgettable Sailing Dream with Lorenzo and Annalisa If you are looking for a perfect sailing experience in the Cyclades, choose Lorenzo and Annalisa. For a week, they guided us from Lavrio to Mykonos, exploring the Small Cyclades, and we were thrilled. Their knowledge of the islands is exceptional, allowing us to discover corners of paradise and ideal sailing conditions. On board, the atmosphere has always been relaxed and welcoming. To report the truly delicious and varied cuisine!! . Their synergy creates a serene and pleasant environment. The Small Cyclades gave us breathtaking landscapes, and thanks to them we fully lived every moment: swimming in deserted bays and dinners in typical taverns. Lorenzo and Annalisa are passionate and experienced travel companions. They exceeded all expectations, turning a vacation into an extraordinary adventure. We highly recommend them to anyone who wants an authentic and unforgettable experience among the Greek islands.

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