Sailing from Santorini to Kos


Sailing cruise itinerary from Santorini to Kos

Our sailing cruise from Santorini to Kalymnos proves to be a unique adventure that combines the challenge of longer and more demanding sailing sections with the pleasure of relaxing days, dedicated to the exploration of crystal-clear bays and deserted islets, far from the routes beaten by mass tourism. Starting from the majestic Santorini, our journey will take us to discover hidden pearls such as Anafi, Astypalea and Pserimos, islands that retain 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 navigation into a fun and rewarding experience. The stability and speed of the boat combine perfectly with the skill of our skippers, true navigators of the sea, who guide the vessel 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 prove 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 culmination of our trip is the arrival in Kalymnos, a fascinating and still little explored island, where nature, culture and local traditions await us to be discovered.

Start your sailing adventure in the spectacular Caldera!

First day of sailing holiday

The journey begins with a late afternoon boarding on the enchanting island of Santorini, a destination that embodies the quintessential beauty of the Aegean Sea. Warmly welcomed aboard our modern and high-performance sailboat, you will immediately feel part of an adventure that promises to be unforgettable. This vessel not only shines with its nautical capabilities, but also offers a comfortable and fun environment, perfect for exploring the wonders of the Greek islands.
After a friendly welcome and once settled in your cabins, you will have the chance to start discovering the unique spirit of Santorini, an island famous for its breathtaking sunsets, its crystal clear waters and breathtaking volcanic landscape.
The evening lights up with a dinner on board, masterfully prepared by our skippers. Not only expert navigators, but also excellent cooks, the skippers will delight you with dishes that reflect the authentic flavors of the Mediterranean, making your first meal on board a culinary experience to remember. Dinner will be served in one of the most evocative and "secret" anchorages of Santorini, inside its imposing caldera. Surrounded by dark waters and volcanic walls, the setting is simply spectacular, offering a start to your journey that touches the heart and soul.

Second day of sailing holiday

The second day begins with a gentle alarm, set to allow you to fully savor the day of navigation and exploration. Leaving Santorini behind, the boat will set sail with a crosswind, heading towards the picturesque Anafi.

This enchanted island is truly a hidden treasure, located off the beaten tourist route. Its proximity to the frenetic Santorini accentuates its discreet charm: Anafi is a sanctuary of peace and authenticity, where time seems to have stopped.

Arriving at your destination, it will immediately become clear to you how unique this island is. The bright colors of the houses contrast with the deep blue of the sea, while quiet reigns supreme. The island is little known but no less enchanting; Anafi will surprise you with its peaceful and genuine climate, offering you a taste of traditional island life.

In the late afternoon, we explore the picturesque village together: its narrow cobbled streets, white churches with blue domes and small taverns will invite you to discover the serene rhythm of local existence. The more adventurous will be able to try their hand at a walk on land, to discover the natural beauty that the island hides.

Crociera in barca vela alle Cicladi Settentrionali

Sailing to the Aegean butterfly

Third day of sailing holiday

We set sail at dawn, leaving peaceful Anafi behind us to head towards Astypalea, the island that enchants with its unique butterfly shape. Navigation abeam promises to be lively and stimulating, an opportunity to feel the strength of the wind and the embrace of the waves while our modern and high-performance boat glides with agility on the sea, offering us moments of pure excitement and freedom.

Astypalea welcomes us by revealing her hidden wonders. The island, a jewel on the border between the Dodecanese and the Cyclades, hides enchanting bays where we take a break in the heart of the afternoon. It is the perfect time to immerse yourself in its crystal clear waters, relax under the warm sun or admire the breathtaking landscape that surrounds us, a perfect combination of uncontaminated nature and tranquility.

With the arrival of the evening, the island is tinged with magic. The highlight of the day is the excursion to the majestic Venetian castle that stands proud on the island. This fortress, silent witness to centuries of history, offers us an unparalleled perspective: a view that embraces the white roofs of the village below, the blue waters of the bays and the infinite horizon of the sea. It is a journey through time, where the past meets the present in a panorama of rare beauty.

The evening ends with a walk in the beating heart of Astypalea. The narrow and winding alleys of the town guide us through scenes of daily life unchanged over time, where the traditional architecture of the white houses, framed by the purple sunset, creates an unforgettable contrast with the deep blue of the sea.

Crociera in barca vela alle Cicladi Settentrionali

Relax in the bays between the islets near Astypalea

Fourth day of sailing holiday

After a hearty breakfast on board, we get ready to explore the enchanting bays of the small islands scattered around Astypalea. These hidden gems are sanctuaries for those seeking peace away from the hustle and bustle of mass tourism, a refuge for those who wish to immerse themselves in the most authentic nature.

The day flows in harmony with the relaxed rhythm of the island, between refreshing swims in the transparent waters and regenerating walks along fine sandy beaches. The serenity of the environment that surrounds you contributes to complete relaxation, whether you choose to sunbathe or prefer more dynamic activities in the water. For sports enthusiasts, there will be no shortage of opportunities to snorkel, enjoying the marine wonders that lie just beneath the surface.

As the sun begins to decline, leaving a day of sun and exploration behind us, we will gather on the beach for an aperitif. The golden sand, the rustle of the waves and a refreshing drink will be the perfect prelude to an unforgettable evening.

And to end the day in style, dinner will be served on board the boat, under a magnificent starry sky. The sky transforms into a stage, with millions of stars dancing in eerie silence. This is the perfect time to raise your glasses, toast life and the new friendships made on board, while the waves gently cradle your houseboat.

Crociera in barca vela alle Cicladi Settentrionali

Challenges and Rewards in the Open Sea: From Astypalea to Pserimos

Sixth day of sailing holiday

Today is the most challenging 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 wind from upwind. Savor 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 today too we will test our seafaring skills with a navigation that the crew and passengers will remember.

After a day at sea, landing in Pserimos will be a sweet relief. With its serene atmosphere and calm waters, this little island is the perfect canvas on which to paint the finale of our day.

We celebrate our sailing successes with a classic of Italian cuisine, just as if we were at home: tagliatelle with meat sauce. Prepared and cooked on the boat, this dinner becomes a special event. Sharing this dinner together will be a way to strengthen bonds and share the stories of this adventurous day.

As the sun sets before our eyes, let's leave behind the teamwork and collaboration that animated this day of sailing, to relax and enjoy the simple but profound pleasures of life at sea.

Crociera in barca vela alle Cicladi Settentrionali

Evening in the vibrant port of Kalymnos

Seventh day of sailing holiday

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 at inaccessible coves and hidden ponds where the water is so clear that you can see the entire underwater world without even diving.

After enjoying the wild beauty of Pserimos and strolling along its stunning beach, it's time to set sail again. In the afternoon, there will be a pleasant 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. You can discover sponge workshops, one of the island's ancient crafts, or simply enjoy a coffee while "people watching" along the lively seafront.

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

Crociera in barca vela alle Cicladi Settentrionali
Crociera in barca vela alle Cicladi Settentrionali

The end of the journey and a goodbye to the next experience

Last day of sailing holiday

With the dawn coloring the sky with delicate shades, we find ourselves together for the last time around the breakfast table. The port of Kalymnos is already alive with movement and sounds, but on our boat the calm and bond that was created between us during this unforgettable adventure still reigns.

The least pleasant moment of our cruise has arrived: saying goodbye. But it's not goodbye; it is rather a goodbye, accompanied by the promise of meeting again soon and sharing the sea, the wind and the stories that only a boat holiday can offer.

As we set foot back on land, rich and vivid memories of the past week crowd our minds: the infinite blue of the sea, the starry sky over enchanting bays, the flavors of Mediterranean cuisine and, above all, the freedom that only sailing can offer .

The bags may be ready to leave the boat, but the experiences lived and the new friends found still remain firm in our hearts. Farewell kisses and hugs are exchanged with the certainty that these days of sailing will become favorite stories to relive until our next meeting.

Crociera in barca vela alle Cicladi Settentrionali

The stages of the itinerary are subject to changes due to weather conditions or other unforeseen circumstances that prevent or make navigation to reach them or mooring difficult. Any changes to the itinerary are implemented exclusively to guarantee better organization of the holiday and to ensure the safety and comfort of our guests.

Sailing from Santorini to Kos ultima modifica: 2024-02-29T18:37:01+00:00 da adminwalkabout