Sailing Cruise Itinerary from Santorini to Kos
Our sailing cruise from Santorini to Kos offers a unique adventure, combining the challenge of longer, more demanding sailing passages with the pleasure of relaxing days exploring crystal-clear bays and deserted islets, far from the beaten tourist tracks. Starting from the spectacular Santorini, our journey takes us to hidden gems like Anafi, Astypalea, Nisyros, and their nearby islets, all of which have retained their wild and authentic beauty.
Anafi is the first of these treasures, an enchanting and secluded island ideal for those seeking peace and authenticity. With its pristine beaches and the majestic Kalamos monolith, one of the tallest in the Mediterranean, Anafi offers a timeless experience dominated by nature and free from mass tourism.
Astypalea, on the other hand, boasts a unique charm with its butterfly-like shape and its position bridging the Dodecanese and the Cyclades. Featuring a Venetian castle and the iconic white-and-blue houses of its village, this island provides breathtaking views and a magical atmosphere, perfect for combining history and unspoiled nature.
Nisyros, a volcanic island, offers a truly one-of-a-kind experience. Here, you can explore its active volcano, craters, and fumaroles, which create a moonlike landscape. The island is also known for its picturesque villages like Mandraki and its natural thermal waters, perfect for relaxation.
Onboard our modern and high-performing yacht, every mile sailed becomes an enjoyable moment. Designed to blend comfort and performance, the yacht allows us to navigate the sea with confidence, turning each sailing stretch into a rewarding experience. The boat’s stability and speed are perfectly complemented by the expertise of your experienced skippers, 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, besides being skilled seafarers, are also excellent chefs, turning every meal onboard into a delightful culinary experience. Using fresh ingredients and gourmet recipes, they treat us to dishes that reflect not only the traditions and flavors of Italian cuisine but also a refined interpretation of international culinary styles. Our days are marked by moments of camaraderie and gastronomic pleasure.
The journey concludes beautifully on the island of Kos, where we find a tranquil spot to dock the boat and relax, surrounded by the island’s charm and the memories of this extraordinary Mediterranean adventure. Kos, with its blend of history and modernity, offers the perfect opportunity to extend the trip with visits to its precious and fascinating archaeological parks, a fitting finale to an unforgettable cruise.
From the spectacular caldera of Santorini, sailing towards the serene Anafi.
First Day of Sailing Vacation
Your journey begins with an afternoon boarding on the enchanting island of Santorini, a destination that epitomizes the beauty of the Aegean Sea. Warmly welcomed aboard our modern and high-performing sailboat, you’ll immediately feel part of an unforgettable adventure. Our **Walkabout sailboat** stands out not only for its nautical excellence but also for providing a comfortable and enjoyable environment, ideal for sailing through the wonders of the Greek islands.
Once you’re warmly greeted and settled into your cabin, take a moment to embrace the unique spirit of Santorini, renowned for its breathtaking sunsets and awe-inspiring volcanic landscapes.
As evening falls, the journey begins with a dinner on board, expertly crafted by your skilled skippers. Not only expert sailors but also exceptional chefs, they will delight you with dishes reflecting the authentic flavors of Italian cuisine, making your first onboard meal a culinary highlight. Dinner will be served at one of Santorini's most stunning and "secret" anchorages, nestled within its iconic caldera. Surrounded by deep waters and dramatic volcanic cliffs, this setting offers a spectacular start to your adventure, touching both heart and soul.
Second Day of Sailing Vacation
The day begins with a gentle awakening, allowing you to savor every moment of this journey of exploration and relaxation. Leaving behind the vibrant Santorini, we hoist the sails and head toward **Anafi**, propelled by a steady beam wind guiding us to this hidden Cycladic gem.
Anafi, off the beaten tourist path, is a sanctuary of tranquility and authenticity. Its proximity to bustling Santorini only enhances its understated charm—an island seemingly frozen in time, offering a serene oasis and an authentic glimpse into island life.
Upon arrival, Anafi’s magic will immediately captivate you with its unspoiled beauty. Though lesser-known, this island enchants visitors with its genuine simplicity and pristine beaches. Spend the afternoon unwinding, swimming in crystal-clear waters, or basking under the sun on the idyllic beach near the harbor.
As the late afternoon sets in, we explore the island’s picturesque village, with cobblestone alleys, whitewashed churches topped with blue domes, and quaint traditional tavernas inviting you to embrace the slow and serene pace of local life.
Exploration and Relaxation on the Island of Anafi
Third Day of Sailing Vacation
Today is dedicated entirely to relaxation and exploration of the enchanting island of Anafi. After a short sail, we anchor in a pristine bay at the foot of the majestic Kalamos monolith. This towering rock formation, one of the highest monoliths in the Mediterranean, stands as a silent guardian, bearing witness to the island's millennia of history.
For those seeking a touch of adventure, there is the option to hike the trail leading to the summit of the monolith, where the Monastery of Panagia Kalamiotissa awaits. The climb is a unique experience: with each step, the view expands, offering breathtaking panoramas of the sea and coastline. The white monastery, nestled into the rock, blends harmoniously with the landscape and provides a serene space for reflection. From the top, the sweeping views of the horizon and the endless sea invite moments of awe and contemplation.
In the late afternoon, we return to Anafi's picturesque little harbor to soak in the authentic charm of the village. Local fishermen mending their nets provide a glimpse into traditional life, as the island begins to glow in the hues of evening.
Later, aboard the Walkabout, a thoughtfully prepared dinner awaits, crafted by your skilled skippers. Tonight's menu offers a surprising twist: an Italian reinterpretation of ethnic cuisine, blending bold flavors with familiar warmth. After dinner, a stroll to the Chora allows us to once again immerse ourselves in the island's magic, wandering through charming alleyways and enjoying the inviting atmosphere of quaint local tavernas.
A perfect day to savor the wild beauty and authentic culture of this stunning island, leaving an indelible mark on every traveler’s heart.
Sailing Towards the Butterfly-Shaped Island of Astypalea
Fourth Day of Sailing Vacation
At dawn, we leave behind the tranquility of Anafi, eager to make the most of a new day filled with adventure. Setting sail towards Astypalea, we ride the beam winds that promise a lively and exhilarating navigation. Our modern and agile sailboat glides over the waves with determination, delivering the pure thrill of sailing: the sound of the sea, the strength of the wind, and an unparalleled sense of freedom accompany us throughout the crossing.
Astypalea welcomes us with its unmistakable butterfly shape, unique and captivating. Situated at the crossroads of the Dodecanese and the Cyclades, this jewel of an island is a perfect blend of cultures and breathtaking landscapes. We drop anchor in one of its hidden bays for a relaxing break and a delicious onboard lunch. The afternoon is devoted to unwinding and exploring the crystal-clear waters of Astypalea, ideal for a refreshing swim or simply basking in the sun, surrounded by pristine nature.
As the sun sets, the island transforms into a magical and timeless place. The highlight of the day is the excursion to the majestic Venetian castle that crowns the island. This ancient fortress, steeped in history, offers us an unrivaled view of the whitewashed rooftops of the village, the turquoise waters of the bays, and the endless horizon of the sea. It’s a journey into the past, where every stone tells a story of centuries gone by and rewards us with an extraordinary panorama.
We conclude the day with a leisurely stroll through the narrow, winding alleys of Astypalea’s charming town center, where the essence of local life remains beautifully preserved. Whitewashed houses stand in stark contrast to the evening sky, framed by a violet-tinged sunset and the deep blue of the sea. Our dinner unfolds in a traditional tavern overlooking the castle, a scene straight out of a postcard, offering one final, unforgettable taste of the island.
A perfect day for those seeking adventure, history, and the authentic magic of the Greek islands.
Relax in the Bays Among the Islets Near Astypalea
Fifth Day of Sailing Vacation
After a hearty breakfast onboard, the day begins with the promise of exploring the enchanting bays of the small islets scattered around Astypalea. These hidden gems are sanctuaries for those seeking peace far from the bustle of mass tourism, offering a haven for anyone wishing to immerse themselves in untouched nature.
The day unfolds in harmony with the relaxed rhythm of the island, featuring refreshing swims in crystal-clear waters and rejuvenating strolls along fine sandy beaches. The serenity of the surroundings promotes complete relaxation, whether you choose to bask in the sun or engage in more dynamic water activities. For the adventurous, there will be ample opportunities for snorkeling, revealing the marine wonders just beneath the surface.
As the sun begins its descent, marking the end of a day filled with sunshine and discovery, we’ll gather on the beach for an aperitif. The golden sands, the gentle sound of the waves, and a refreshing drink create the perfect prelude to an unforgettable evening.
To cap off the day in style, dinner will be served onboard, under a magnificent starlit sky. The heavens transform into a stage, with millions of stars dancing in supernatural silence. It’s the perfect moment to raise your glass, toast to life, and celebrate the new friendships forged onboard, all while the gentle waves cradle your floating home.
Challenges and Rewards on the Open Sea: From Astypalea to Nisyros
Sixth Day of Sailing Vacation
Today brings the most thrilling navigation of your sailing adventure! At dawn, we set sail from Astypalea, heading towards the volcanic island of Nisyros, waiting for us at the end of an exciting open-sea crossing.
With the sails catching the wind, the boat picks up speed, gliding through the waves with agility and responding effortlessly to the helm's movements. This day of navigation offers an authentic experience, full of challenges and adrenaline, perfect for those eager to test their sailing skills.
By late morning, we arrive at Nisyros, a volcanic island with unparalleled landscapes. Among its highlights is the Stefanos Crater, where you can walk along the volcano’s base and observe up close the fumaroles releasing sulfuric vapors. The island also boasts the village of Nikia, perched 400 meters above sea level, where whitewashed houses and narrow cobblestone streets provide breathtaking views of the caldera. Other must-see spots include the village of Mandraki, home to the Panagia Spiliani Monastery nestled in a cave, and the natural thermal springs of Loutra, perfect for a relaxing soak.
Nisyros is authentic and distinct from other Cycladic islands—a world unto itself that offers a journey through surreal landscapes and untamed nature.
Last Evening Aboard in the Beautiful Bay of Kefalos
Seventh Day of Sailing Vacation
Our week of sailing continues with another unforgettable day. As we wake up, we gear up to explore the small island of Jali, a hidden paradise renowned for its unique natural beauty. Aboard the dinghy, we access secluded coves and crystal-clear lagoons, where the water is so transparent it reveals the underwater world without even diving in. Here, we’ll discover the white pumice cascades, marveling at the surreal landscape and having fun sliding down the volcanic stone formations.
After thoroughly enjoying every corner of this special island, it’s time to set sail once more. In the afternoon, we embark on a pleasant navigation towards Kos, with our final destination being Kefalos, a picturesque bay where our unforgettable sea adventure draws to a close.
Moored in the expansive bay of Kefalos, you’ll have the chance to explore the beach and enjoy a leisurely stroll along the shore, taking in the beauty of this serene spot on the island. To celebrate a week of exploration and adventure, a special dinner awaits us on board: a classic of Italian cuisine, tagliatelle with ragù, lovingly prepared by our skippers. This meal, crafted with care and shared in good company, becomes a unique moment to strengthen bonds and relive the day’s emotions.
As the sun sets over the sea, we toast to teamwork and camaraderie, the essence of what made this cruise so special. In an atmosphere of festivity and togetherness, we prepare to close this week of sailing with one last moment of joy and community beneath the stars.
Farewell to the Sea and Fellow Travelers
Last Day of Sailing Vacation
As the first light of dawn paints the sky in soft hues, we gather for one last breakfast together, savoring the tranquility that still envelops our boat while Kefalos Bay slowly comes to life. The atmosphere is imbued with a special bond, built day by day during this unforgettable adventure.
The most challenging part of the cruise has arrived: the goodbyes. Yet, more than a farewell, it’s a heartfelt "see you soon," accompanied by the promise to meet again amidst waves, winds, and sunsets. We leave the boat with our hearts full of indelible memories: turquoise waters, starry skies above quiet bays, the flavors of Mediterranean cuisine, and the incredible freedom that only sailing can offer.
As we head back to the mainland, our bags are packed, but it feels as though a part of us remains anchored to this adventure, a lasting connection in our hearts. With hugs and smiles, we part ways, knowing that these days of sailing will be among the stories we carry with us, to relive and share until our next voyage together.
The itinerary stops are subject to changes due to weather conditions or other unforeseen circumstances that prevent or make navigation or mooring difficult. Any modifications to the itinerary are implemented solely to ensure better organization of the vacation and to guarantee the safety and comfort of our guests.