Itinerary of the Sailing Cruise from Mykonos to Milos
Embark on an Unforgettable Sailing Adventure from Mykonos to Milos
Guided by two expert Italian skippers, this sailing vacation will take you through the stunning Cyclades Islands, offering a unique journey enhanced by refined Italian cuisine served onboard, all enveloped in the magic of the Aegean Sea.
Our yacht, designed to combine comfort and performance, ensures swift and safe navigation between islands. Feel the adrenaline of speed without sacrificing relaxation and the pleasure of embracing the sea in total comfort.
Your adventure begins in iconic Mykonos, one of Greece's most celebrated destinations, renowned for its cosmopolitan lifestyle, golden beaches, and vibrant nightlife. With direct flights from Italy, it’s the ideal starting point for this extraordinary journey. From the bustling Mykonos, we escape to discover the secluded island of Rineia, a hidden gem of unspoiled beauty. This wild and uninhabited island welcomes you with pristine beaches and crystal-clear waters, offering peace and tranquility for those who seek the simple and untouched beauty of the Aegean Sea.
A stone’s throw from Rineia lies Delos, one of Greece’s most important archaeological sites and a UNESCO World Heritage Site. This small island was a significant religious and commercial hub in antiquity and is steeped in Greek mythology as the birthplace of Apollo and Artemis. Explore ancient ruins, including temples, mosaics, and theaters, which tell the story of a millennia-old civilization. It’s a true journey back in time and a cultural experience that will leave you in awe.
Continuing our voyage, we arrive at Syros, an island that harmoniously blends history and modernity. The vibrant capital, Ermoupoli, is the heart of the Cyclades. With its neoclassical buildings, theaters, and squares reflecting its illustrious maritime past, Ermoupoli is famed for its elegant architecture and the contrast between the Catholic district of Ano Syros and the Orthodox quarter. Stroll through the lively streets and savor traditional dishes at welcoming local taverns.
A thrilling sail brings us to Serifos, an island with an authentic and relaxed atmosphere. Its Chora, perched atop a hill, will amaze you with its whitewashed houses and panoramic sea views. Serifos is perfect for those seeking a less crowded Greece rich in charm and tradition. Here, nature takes center stage with secluded beaches, tranquil bays, and trails winding through mountains and olive groves.
Next, we head to Sifnos, stopping in one of its most beautiful bays, once a pirate’s haven, where you can swim in turquoise waters and bask in the sun. Sailing forward with the wind at our backs, we reach Polyaigos, one of the wildest and most pristine islands in the Cyclades. A true natural paradise, Polyaigos is famed for its crystal-clear waters, ranging from turquoise to deep blue, hidden caves, and colorful rock formations that shift hues at sunset. It’s a perfect oasis for snorkeling or simply marveling at the breathtaking scenery.
A final exhilarating sail takes us to Milos, one of the most spectacular islands in the Aegean Sea. Famous for the Venus de Milo statue now displayed in the Louvre, this island will captivate you with its volcanic formations, white sandy beaches, and secluded coves accessible only by sea. Steeped in ancient history, Milos is a blend of lunar landscapes, traditional villages, and natural hot springs. Every corner of Milos invites you to uncover a piece of paradise.
This sailing vacation is more than just a cruise: it’s an immersion into the breathtaking beauty of the Greek islands, their fascinating history, and the authentic flavors of the Mediterranean. Thanks to the warm hospitality and expertise of your Italian skippers, every moment will be a cherished memory. Get ready to sail the waves, explore enchanting places, and experience a vacation that will stay in your heart forever.
Boarding in Mykonos on the First Day: A Blend of History and Tranquility
First Day of Your Sailing Vacation
Begin your enchanting sailing vacation by boarding in the heart of the Cyclades, Mykonos. We will welcome you onboard in the late afternoon, introducing you to what will be your home for the week ahead.
Once all guests are settled into their cabins, we’ll hoist the sails and set course for a peaceful bay, far from the bustling nightlife of Mykonos. Here, the atmosphere transforms into something magical: as the sunset’s golden reflections dance on the water, your skippers will don their chef hats to prepare a delicious dinner.
Savor your first evening at sea under a star-studded sky, then let the gentle waves lull you to sleep on your first night onboard.
Delos, an archaeological site of inestimable value, steeped in ancient Greek mythology
Second Day of Your Sailing Vacation
With the refreshing Aegean wind filling the sails, your day begins with a wholesome breakfast on board. A short and enjoyable sail will take you to the sacred island of Delos, a site of immense archaeological value. In ancient times, Delos was considered the most famous and sacred of all the islands, mythically known as the birthplace of Apollo and Artemis.
In the afternoon, your adventure continues toward Rineia, Delos' quieter and less-traveled twin island, just a short sail away. Here, tranquility reigns supreme. Enjoy a sunset aperitif in the cockpit, watching as the golden light bathes the serene landscape. Later, your dinner, lovingly prepared and served by your skilled skippers, offers the perfect blend of delicious cuisine and the camaraderie of newfound friends.
The silence of Rineia provides an ideal setting for a peaceful evening, while the vibrant energy of nearby Mykonos shimmers in the distance, its lights casting a faint glow on the horizon.
Wind in the Sails to Syros, the Capital of the Cyclades
Day Three of Your Sailing Vacation
Your third day at sea promises an exhilarating experience as our sailing yacht, powered by a lively beam reach wind, embarks on a navigation adventure sure to delight sailing enthusiasts. It’s the perfect day for those eager to learn, with opportunities to practice maneuvers or take the helm and truly connect with the essence of the sea.
This swift sail concludes with our arrival at a tranquil and welcoming anchorage.
In the afternoon, we dock at the vibrant port of Ermoupoli, the heart of Syros and the capital of the Cyclades. Stroll through its neoclassical streets, marvel at the stunning architecture, and lose yourself in the lively alleys brimming with history and culture.
As the sun begins to set and the harbor lights twinkle to life, you’ll be enveloped in the vibrant charm of island life. End the day with a delightful local dinner, savoring traditional Greek dishes, and toast to another beautiful day on the sea.
Taking the Helm and Practicing Maneuvers to Reach the Island of Serifos
Day Four of Your Sailing Vacation
Leaving behind the vibrant capital of Syros, we set sail along its southern coast before crossing the majestic Aegean Sea channel, where the deep cobalt blue of the water stretches endlessly to the horizon. Our destination: the enchanting island of Serifos.
As the boat glides through the waves, feel the energy of the wind and the sea around you. If you wish, you can actively participate in the onboard maneuvers—an unparalleled opportunity to learn the basics of sailing—or simply relax and admire the breathtaking panorama of sea and sky blending into one.
We anchor in front of a postcard-perfect golden beach, where crystal-clear waters invite you for a refreshing swim. Onboard, enjoy a light and refreshing lunch, prepared with fresh ingredients and infused with Mediterranean flavors. Afterward, the sea becomes your playground: unwind with a revitalizing swim or explore the underwater world with snorkeling, discovering the vibrant marine life.
In the late afternoon, we arrive at the stunning bay of Livadi. From here, a leisurely walk takes us to the Chora of Serifos, the old village perched atop the hill. The panoramic view of the surrounding islands at sunset is nothing short of spectacular—a breathtaking scene where the setting sun paints the sky with golden and rosy hues.
The day ends with a traditional dinner at a local taverna, where you’ll savor authentic Greek dishes, accompanied by the warmth of local hospitality and a captivating view of the bay. Finally, we gather in the main square of the Chora to enjoy a local liqueur, soaking in the authentic atmosphere of the village. Whitewashed houses adorned with vibrant flowers and colorful shutters add a magical touch to the evening, creating a memory you’ll treasure forever.
A perfect day of sea, culture, and flavors that will leave an indelible mark on your vacation.
Sailing Towards the Stunning Sifnos
Day Five of Your Sailing Vacation
The day begins with our bow pointed toward Sifnos. We hoist the sails, and with the wind at our back, our boat glides swiftly over the sparkling waters of the Aegean Sea. The pace of the navigation is dynamic and adventurous, perfect for those seeking a thrill during their sailing holiday.
As we sail along the eastern coast of Sifnos, the island’s wild and authentic landscapes unfold before us. Our first stop is a secluded and untouched bay, accessible only by sea—a true slice of paradise far removed from the crowds. Here, we revel in the serenity, surrounded only by the sound of the waves and the scent of the sea. Likely, we’ll be the only visitors, offering an intimate and unique experience.
After a delicious lunch prepared onboard, we continue our journey to a second cove that feels like it belongs in a pirate tale. The only signs of human presence are a small house and a white chapel perched on the cliffs, adding a touch of charm to the already captivating scenery.
The evening wraps up with a gourmet dinner prepared by your skippers as the sky above us fills with stars. Far from light pollution, we find ourselves stargazing, identifying constellations, and marveling at a rare and precious natural spectacle. It’s a magical moment, one that only a sailing vacation in Greece can provide.
And for the lucky ones who spot the most shooting stars, a little surprise awaits!
The Largest Uninhabited Island in Greece: The Natural Paradise of Polyaigos
Day Six of Your Sailing Vacation
Start your day in the best way possible: a refreshing morning dive into the crystal-clear waters surrounding the boat. It’s the perfect way to wake up, energize your body, and embrace the day. After a rejuvenating breakfast onboard, we hoist the sails and let the wind guide us on a downwind journey toward the stunning island of Polyaigos, one of the wildest and most pristine gems of the Cyclades.
Polyaigos, with its dreamlike beaches and turquoise waters, is a true paradise for those seeking natural beauty and tranquility on a sailing vacation. Its bays, hidden treasures with white sandy beaches and incredibly clear waters, are perfect for snorkeling explorations. The dramatic rock formations surrounding the island create a breathtakingly picturesque setting.
Our destination for the evening is Faros Bay, a natural marvel straight out of a postcard, where the sea shifts from deep blue to emerald green. Often deserted, the beach provides an ideal retreat for relaxation, sunbathing, and swimming in transparent waters.
For the more adventurous, a sunset hike to the lighthouse overlooking the bay offers an unforgettable panorama, with views stretching across the Aegean in all directions.
As an uninhabited island, Polyaigos offers an unparalleled sense of authenticity: we’ll be surrounded only by nature and silence, far from the trappings of civilization.
The evening concludes with a gourmet dinner lovingly prepared by your skippers, served under a star-filled sky. Far from light pollution, the Milky Way reveals itself in all its brilliance, inviting us to identify constellations and soak in the cosmic wonder. This rare and precious experience is the essence of a sailing vacation in such untouched locations—a magical moment to cherish forever.
Milos: The Island of Volcanic Contrasts and Dreamlike Beaches
Seventh Day of Your Sailing Vacation
As dawn breaks on the penultimate day of this extraordinary sailing adventure, we hoist the sails and set course for the magnificent island of Milos, the final destination of a week spent exploring the crystal-clear waters of the Aegean. Known for its volcanic landscapes and breathtaking beaches, Milos is the perfect grand finale to this unforgettable journey.
If the wind conditions are favorable, we’ll stop at Sarakiniko, one of the most iconic beaches in Greece. Its white cliffs, sculpted over time by wind and waves, create a lunar landscape that feels otherworldly. The striking contrast between the blinding white rocks and the deep blue sea will leave you in awe. It’s the perfect spot for a refreshing swim or simply to relax and soak in the extraordinary surroundings.
By early afternoon, we’ll arrive at Adamas, the main port of Milos. This charming village blends traditional Greek charm with a lively and welcoming atmosphere. Stroll along the waterfront, admire the gently swaying boats, explore local shops, or enjoy a coffee with a view of the sea as the sun begins to set, painting the sky in warm hues.
One of the day’s highlights is sure to be the sunset from the top of Profitis Ilias Monastery. From this vantage point, the panoramic view of Milos and the Aegean bathed in sunset colors is truly enchanting.
The evening will culminate with a memorable dinner in Plaka, the island’s historic village. Wander through its cobblestone streets, immerse yourself in the authentic and relaxed atmosphere, and savor the flavors of traditional Greek cuisine. It’s the perfect way to close a day filled with discoveries and emotions.
Final Day of Your Sailing Vacation
As our journey comes to an end, we prepare for disembarkation. Before parting ways, we want to thank you for sharing this adventure through the untouched beauty of the Greek islands. As your feet touch solid ground, we hope you carry with you memories of an authentic and unforgettable experience.
This sailing trip was more than just a vacation—it was a complete immersion in nature and the sea, leaving you longing to return for more adventures. It’s a unique way to disconnect from the hustle and bustle of city life and reconnect with the rhythm of the waves.
Until next time—see you for another adventure on the waves!
The itinerary stops are subject to change due to weather conditions or other unforeseen circumstances that may prevent or make navigation or mooring inconvenient. Any modifications to the itinerary are made solely to ensure better trip organization and to guarantee the safety and comfort of our guests.