Sailing Cruise Itinerary from Mykonos to Santorini
This sailing vacation begins in Mykonos, in the heart of the Cyclades. We will set sail in the late afternoon to reach a peaceful bay. The following day is dedicated to visiting ancient Delos, followed by a relaxing afternoon in the crystal-clear waters of Rineia.
Continuing on, we head toward Naxos, starting the morning exploring rocky islets before arriving at the lively Chora, dominated by the striking Portara and the Venetian Kastro. An exciting sailing journey take us to Koufunissi, where natural pools and scenic stops await, before finally exploring the remote bays of Keros, an ideal spot to watch for dolphins, turtles, and, with a bit of luck, the monk seal.
Taking advantage of a favorable wind, we arrive at Iraklia, a secluded and peaceful island, for a swim in a bay featuring a shipwreck visible even from the surface. In the afternoon, we set course for Ios, where we can enjoy the sunset from its lively Chora. The adventure continues with a trip to explore Ios before sailing on to Santorini, where the contrast between the black volcanic rock and the white villages perched on the caldera’s edge offers a breathtaking view. The evening wraps up with a dinner on land in the picturesque village of Oia, immersed in the island’s timeless charm.
Throughout this sailing vacation, you will spend your nights at anchor in the bay, falling asleep to the gentle motion of the waves in the stillness of the night, gazing at the starry sky in an atmosphere of total serenity.
On board, you will be welcomed by two experienced Italian skippers who will not only guide you through some of the most enchanting islands in the Aegean Sea but also let you savor the delights of Italian gourmet cuisine, turning every meal into a gastronomic journey. Our vessel, a fast-cruiser oceanic sailing boat, is designed to offer you maximum comfort without compromising on performance: you will enjoy swift and thrilling sails, accompanied by the sound of the wind filling the sails and the adrenaline of reaching captivating destinations.
Kick Off Your Adventure in Mykonos
Day 1:
Your unforgettable sailing holiday through the Cyclades begins in Mykonos, easily reached by direct flights from Italy. Once on board, after settling into your cabins and getting to know the crew, we’ll weigh anchor and head to a peaceful bay, far from the island’s hustle and bustle. There, you’ll spend the night gently rocked by the sea.
The day culminates with a dinner on board, prepared by our skippers who will spoil you with fresh, genuine flavors. It’s a convivial and relaxing moment, perfect for immediately diving into the unique atmosphere of this sailing vacation in the Cyclades.
Exploring Ancient Delos and Relaxing in Rineia’s Crystal Waters
Day 2
The morning is dedicated to exploring the archaeological park of Delos, a place steeped in history and charm where you can relive ancient legends and soak up the atmosphere of classical Greece. After lunch, we set sail for Rineia and drop anchor in a bay of crystal-clear waters, perfect for relaxing or enjoying water activities on the beach. The day wraps up with dinner on board, followed by an evening spent gazing at the starry sky, fully immersed in harmony with the surrounding nature.
Toward Naxos: Hidden Bays and the Charm of the Chora
Day 3
The day begins with an exploration of the jagged rocks and tiny islets along the bay, a natural paradise to savor in perfect tranquility. In the afternoon, we harness a favorable breeze to sail downwind toward Naxos, the largest of the Cyclades, celebrated for its lively atmosphere and authentic charm.
As evening falls, we delve into the winding streets of the Chora, welcomed by the imposing Portara— the majestic gateway to the Temple of Apollo overlooking the sea—an ideal vantage point for a breathtaking sunset. Moving on, we lose ourselves in the labyrinth of alleys leading to the Venetian Kastro, where a unique view of the harbor and the town awaits. Along the way, we discover artisan shops offering local products.
Nightfall brings a burst of lights and fragrances in the local tavernas, where Greek cuisine and the warm hospitality of the islanders make the experience even more unforgettable.
Sailing with the Wind at Our Backs: The Wonder of Koufunissi
Day 4
With the wind at our backs, we glide swiftly over the waves, turning the crossing to Koufunissi into a thrilling experience as the boat skims over the sea. Along the way, we enjoy a refreshing stop at the natural pool of Porí, a glimpse of this island’s surprising beauty.
A scenic walk invites us to explore the rugged coastline, where delightful beaches alternate with natural pools. Among these, the most famous is Koufunissi’s “Devil’s Eye,” an absolute must for anyone wanting to take a memorable swim.
For those eager to extend the fun, the beachside bars offer the chance to savor a drink while admiring the captivating island of Keros, creating a magical, laid-back atmosphere that continues well into the evening.
In Search of the Wonders of Keros: Remote Bays and Extraordinary Encounters
Day 5
This day is entirely devoted to exploring the most secluded bays of the uninhabited island of Keros, a true hidden gem in the heart of the Cyclades. During our journey, we might spot sea turtles, dolphins, and, with a stroke of luck, even the Mediterranean monk seal. Surrounded by tranquility and pristine nature, we immerse ourselves in this little paradise untouched by time, creating unforgettable memories for every traveler’s heart.
The Hidden Charm of Iraklia and a Lively Evening in Ios
Day 6
Taking advantage of a steady beam reach, we sail swiftly toward the remote island of Iraklia, rarely visited by mass tourism and home to a peaceful, unspoiled atmosphere. In a bay of exceptionally clear water, we drop anchor to explore a shipwreck visible even from the surface, adding a touch of mystery to our stop.
By early afternoon, we head out again, setting course for Ios and mooring in its bustling harbor. As the sun sets, we make our way up to the Chora to soak in its vibrant evening vibe and enjoy spectacular views of the surrounding islands bathed in golden light. We end the day with a plate of homemade tagliatelle with ragù, prepared on board, making dinner a moment of genuine conviviality and flavor.
Toward Santorini: The Allure of the Caldera and Its Magical Sunset
Day 7
The day begins with a two-wheeled adventure, exploring the island of Ios on a scooter. Starting from the lively Chora, with its picturesque cobblestone alleys, you can venture among characteristic windmills and whitewashed chapels perched among the houses. A must-see stop is the Church of Panagia Gremiotissa, offering breathtaking views of the sea and surrounding hills, as well as the evocative Odysseas Elytis Theater. Wandering through the narrow streets, you’ll discover small shops, enchanting vistas, and the island’s genuine way of life, which moves at a pleasantly relaxed pace.
After lunch, we raise the sails and head for Santorini. Arriving by boat is a one-of-a-kind experience: the contrast between the black volcanic rock and the gleaming white villages perched on the edge of the caldera—framed by a deep blue sky—creates a stunning first impression. We sail through the submerged crater and pause for a rejuvenating swim, immersed in one of the most captivating landscapes in the Aegean Sea.
We continue our voyage toward the famous Red Beach, known for its almost surreal red sand backdrop.
At the end of this day filled with excitement, we treat ourselves to dinner on shore, savoring the rich local cuisine and the incomparable charm of Santorini.
An Emotional Farewell
Last Day
After breakfast, the least pleasant part of any cruise arrives: saying our final goodbyes. With a wealth of unforgettable memories and the promise of meeting again soon, you will leave the boat that has guided you through this remarkable adventure, carrying in your heart the smiles, sunsets, and shared moments you experienced together.
The stages of the itinerary are subject to change due to weather conditions or other unforeseen circumstances that prevent or make it difficult to navigate to them or dock. Any changes to the itinerary are made exclusively to ensure better organization of the holiday and to ensure the safety and comfort of our guests.