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Fast sailing Santorini-Kos (Kalymnos)

Next Departure:

June 21, 2025

Greece:

Cyclades

Duration:

6 days - 7 nights

Max number of passengers:

6 people

Available:

June

Suitable for travellers:

> 10 years

Boarding from:

Akrotíri

What's included

Cancellation policy

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Super!

Organised by:

Lorenzo & Annalisa

Member since 2013 -

Organisation

Italian

English

French

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8 travellers have chosen this experience

This experience, in a nutshell

Our sailing cruise from Santorini to Kalymnos proves to be a unique adventure that combines the challenge of longer and more challenging stretches of sailing with the pleasure of relaxing days, dedicated to exploring crystal clear bays and deserted islets, far from the beaten track of mass tourism.




Starting from the majestic Santorini, our journey will take us to discover hidden gems such as Anafi, Astypalea and Pserimos, islands that preserve their wild and authentic beauty intact.

On board our modern and high-performance boat, every mile sailed becomes a moment of pleasure. Our boat, designed to combine comfort and performance, allows us to face the sea with confidence, transforming sailing into a fun and rewarding experience. The stability and speed of the boat are perfectly combined with the skill of our skippers, true navigators of the sea, who guide the boat through the turquoise waters of the Aegean Sea with skill and passion.




But it's not just the sailing that makes this cruise unforgettable. The skippers, in addition to being skilled sailors, also turn out to be excellent cooks, capable of transforming every meal on board into an opportunity to enjoy exquisite dishes. Using fresh ingredients and gourmet recipes, they delight us with culinary creations that reflect the tradition and flavors of the Mediterranean, enriching our days with moments of conviviality and gastronomic pleasure.



The highlight of our journey is the arrival in Kalymnos, a fascinating and still little explored island, where nature, culture and local traditions are waiting to be discovered.


€950

6 days - 7 nights

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9+

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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:

Akrotíri.

Check-in: 6:00 PM

Our trip ends here:

Kos Town.

Check-out: 9:00 AM

Leg 1

Caldera of Santorini

Warmly welcomed aboard our modern and high-performance sailboat, you will immediately feel part of an adventure that promises to be unforgettable. Not only does this boat shine with its nautical skills, but it also offers a comfortable and fun environment that is perfect for exploring the wonders of the Greek islands.

After a friendly welcome and once settled into the cabins, you will have the chance to start discovering the unique spirit of Santorini, an island famous for its breathtaking sunsets, crystal clear waters, and volcanic landscape that leaves you breathless.

The evening lights up with a dinner on board, masterfully prepared by our skippers. Not only experienced sailors, but also excellent cooks. Dinner will be served in one of Santorini's most impressive anchorages, inside its imposing caldera. Surrounded by dark waters and volcanic walls, the setting is simply spectacular.

Leg 2

Anafi

We hoist the sails early and as Santorini fades on the horizon, our modern and high-performance boat takes off, skilfully sailing with the wind crosswise towards the destination of the day: the picturesque Anafi.

As soon as you land on this enchanting island, the singularity of Anafi is revealed in all its splendor. The bright colors of its houses form a vivid contrast to the deep blue of the surrounding sea, and a sense of peace pervades the air.

In the late afternoon, we enter the heart of its picturesque village. Strolling through the narrow cobbled streets, admiring the whitewashed churches with their iconic blue domes, and sitting in one of the cozy local tavernas becomes an invitation to slow down and synchronize with the relaxed pace of Anafi. For adventurous spirits, a walk through the island's paths will reveal corners of unspoiled nature and breathtaking views that only such a magical place can offer.

Leg 3

Astipalea

We set sail at dawn to head towards Astypalaia. Sailing across, promises to be lively and stimulating, an opportunity to feel the force of the wind and the embrace of the waves while our boat, modern and performing, glides with agility on the sea, offering us moments of pure excitement and freedom.

Astypalea welcomes us by revealing its hidden wonders. The island hides enchanting bays where we take a break in the middle of the afternoon. It's the perfect time to dive into its crystal-clear waters and relax under the warm sun.

The highlight of the day is the excursion to the majestic Venetian castle that stands proudly on the island. This fortress offers us a view that embraces the white roofs of the village below, the blue waters of the bays and the infinite horizon of the sea.

The evening ends with a walk through the winding alleys to admire the traditional architecture of the white houses, framed by the sunset.

Leg 4

Astipalea

The fourth day sees us set sail for the secret bays around Astypalaia, true havens of peace away from mass tourism. After a hearty breakfast, we explore these hidden gems, indulging in swimming in the crystal clear waters and walking on fine sandy beaches. The day is spent relaxing and activities such as snorkeling, admiring marine life below the surface.

At sunset, we gather on the beach for an aperitif, surrounded by the relaxing sounds of the sea, a prelude to an unforgettable evening. Dinner on board, prepared by your skippers, marks the highlight of the day. Under a starry sky, we toast to the life and friendships born in this adventure, while the boat gently cradles us, promising new discoveries in the days to come.

Leg 5

Exciting sailing

Today is the most exciting sailing day of our sailing holiday. At dawn, we prepare to depart from Astypalea and head towards the quiet island of Pserimos, which awaits us at the end of a lively crossing.

As we hoist the sails, the boat comes alive with the blowing of the windward wind. Relish the thrill of cutting through the waves with speed, of feeling the wind whistling through the sails and the rudder responding promptly under your hand. The challenges that the open sea presents us are also the most rewarding, and even today we will put our seafaring skills to the test with a navigation that the crew and passengers will remember.

After a day at sea, landing in Pserimos will bring peace and relaxation. With its serene atmosphere and calm waters, this small island is the perfect canvas on which to paint the end of our day with a great dinner prepared by the skippers.


Leg 6

Kalymnos

Our week continues with another unforgettable day on a sailing boat. As soon as we get up, we embark on a new exploration of Pserimos, aboard the dinghy, arriving in inaccessible coves and hidden ponds where the water is so clear that you can see the whole underwater world without even diving.

After enjoying the wild beauty of Pserimos and strolling along its wonderful beach, it's time to set sail again. In the afternoon, there will be a leisurely sail that will take us to Kalymnos, an island famous for its impressive cliffs and as the climbing capital of the world.

After mooring in its large bay, you will have the freedom to explore the country.

In the evening, we will have a dinner on land to experience the cuisine of Kalymnos. It will be time to toast to the experience, culminating this last night of the trip in an atmosphere of celebration and community.

Leg 7

Last day

With the sunrise coloring the sky with delicate shades, we gather together for the last time around the breakfast table. The port of Kalymnos is already alive with movement and sounds.


The least pleasant moment of our cruise has arrived: the goodbyes. But it's not goodbye; It is rather a goodbye, accompanied by the promise to meet again soon and to share again the sea, the wind and the stories that only a sailing holiday can offer.

The luggage may be ready to leave the boat, but the experiences we have had and the new friends we have made are still strong in our hearts. Kisses and goodbye hugs are exchanged with the certainty that these days of sailing will become the favorite stories to relive until our next meeting.

Frequent questions

The organiser reviews

avatar image

Super!

Organised by:

Lorenzo & Annalisa

Member since 2013 -

Organisation

Italian

English

French

4.9/5

out of

40

reviews

Skipper

Boat

Destination

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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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A week exploring the Dodecanese

07/9/2024

Matteo C.

-

Switzerland

Trattamento da crociera, no stress, non devi pensare a niente, non devi decidere niente

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