Itinerary for the Sailing Cruise in the Western Cyclades
Embark on a Dream Sailing Adventure in the Cyclades
We’ll start from Milos, a stunning Greek island in the Cyclades, known for its extraordinary landscapes, crystal-clear bays, and charming traditional villages. Just a short distance away, we’ll visit one of our favorite stops: Poliaigos, an uninhabited island accessible only by sea. Here, we’ll drop anchor in a cove where the boat seems to float on air, thanks to the incredible clarity of the water.
From there, we’ll sail toward Paros, enjoying exhilarating and fast crossings with beam and broad-reach winds. Aboard the Walkabout, an ocean-going fast cruiser known for its stability and suitability for the challenging Aegean conditions, every crossing becomes an exciting adventure.
Our itinerary includes stops at other stunning islands, each offering unique and remarkable beauty:
- Kimolos, a small, peaceful island where the authentic charm of Greek life is revealed in the picturesque village of Chorio, rich in tradition and allure.
- Sifnos, where we’ll anchor in the evocative Pirates’ Bay, once a hidden refuge for ships. Sifnos also offers the chance to visit the medieval Kastro, a fortified village with breathtaking sea views and centuries of history.
- Antiparos, a captivating island with a chic village full of boutiques and traditional shops. Here, we’ll explore the archaeological park of Despotiko, located on a nearby islet that hosts significant ancient artifacts. The turquoise sea and rugged landscape create an enchanting atmosphere.
Every island we visit is a unique discovery, showcasing the best of Cycladic nature and culture, making this journey a true immersion into the authentic beauty of the Cyclades.
An Unforgettable Sailing Vacation
This adventure is perfect for those seeking an unforgettable experience, combining the thrill of fast sailing with relaxation in pristine bays, where you can immerse yourself in nature and enjoy the sea.
Onboard, your experienced skippers will not only expertly handle the boat but also prepare delicious meals, offering you the joy of fine dining in an unparalleled natural setting.
This is the perfect vacation for lovers of the sea, sailing, and the authentic charm of the Cyclades!
Embarkation and Welcome in Milos - Exploring Kleftiko: A Day of Sea and Legends
SATURDAY:
In the late afternoon, we meet at the port of Adamas on the island of Milos, ready to begin this sailing adventure. After boarding, a welcome aperitif and toast set the tone for the convivial and relaxed spirit that will define our cruise. Guests can then settle into their cabins and get familiar with the boat. The evening offers a perfect opportunity to enjoy the lively atmosphere of the harbor and get to know your fellow travelers, letting the excitement for the days ahead build.
SUNDAY:
After departing the expansive bay of Milos, we sail about ten nautical miles with a tailwind to reach the island’s southwestern tip, home to the spectacular Kleftiko. Renowned for its towering rock formations, Kleftiko features impressive sea stacks rising from the water and a coastline dotted with mysterious caves that, according to legend, once provided refuge to pirates.
We’ll anchor over a sandy seabed, surrounded by crystal-clear waters and enchanting cliffs. The white rocks, streaked with shades of red, green, and yellow, create a stunning natural spectacle, making Kleftiko one of the most breathtaking landscapes in the Cyclades.
Exploring the caves by dinghy, we venture into their recesses with flashlights. The light reveals vibrant rock walls and shadowy patterns, adding to the allure of the experience. Each crevice seems to hold a secret, offering a truly unique and unforgettable exploration of this wild and fascinating natural wonder.
The afternoon flows peacefully with swims in the pristine waters and strolls along the long white beach. Relaxing onboard becomes even more magical as the sun sets, casting warm, enveloping colors over the cliffs and transforming the scenery into a living masterpiece.
We end the day with a delicious dinner onboard, spending the night anchored in the bay. Rocked gently by the sea and surrounded by the raw beauty of Kleftiko, we’ll drift off into a peaceful slumber.
Exploration and Sailing to Polyaigos
MONDAY:
The day begins with a special stop to admire the spectacular sandfalls, a fascinating natural phenomenon where sand cascades down the rocks like a waterfall, creating a unique and mesmerizing landscape. After this pause, we set sail on an upwind navigation. Depending on the wind, this leg of the journey can be both intense and invigorating as we head toward our next destination: Polyaigos, a wild and uninhabited island.
Upon arrival, we anchor in one of the most beautiful bays in the Cyclades—a true natural swimming pool with crystal-clear waters and white sand, perfectly sheltered from the Meltemi winds. Here, a peaceful afternoon awaits, with refreshing swims and time to immerse yourself in the pristine beauty of the island.
As the sun sets, we’ll take a short hike along a mountain trail to enjoy an unforgettable view of the horizon as the sky is painted with warm and vibrant colors.
The day concludes with a gourmet dinner onboard, lovingly prepared by your skippers, transforming the evening into a special culinary experience. We’ll spend the night anchored in this secluded bay, lulled by the silence and magical atmosphere of Polyaigos.
Exploring Polyaigos and Sailing to Kimolos
TUESDAY:
We continue our exploration of Polyaigos, an uninhabited gem in the Cyclades that offers breathtaking landscapes and spectacular hidden spots. This morning, we’ll uncover another enchanting corner of this wild island, with turquoise waters and rare natural beauty that will leave you in awe.
In the afternoon, we set sail for nearby Kimolos, an authentic and welcoming island that feels like a journey back in time to traditional Greece. Upon arrival, we’ll explore the picturesque village of Chorio, with its whitewashed houses, narrow alleys, and peaceful atmosphere that invites you to slow down and savor every detail.
The day concludes with dinner at a traditional local taverna, where we’ll enjoy authentic Greek dishes, surrounded by the pleasant and relaxed ambiance of Kimolos.
Sailing and Exploring Sifnos
WEDNESDAY:
After an exhilarating upwind sail, we arrive at a secluded bay on the southern side of Sifnos, an island known for its authentic beauty. This narrow bay, accessible only by sea, is a tranquil and magical spot, dominated by a solitary white house and a small chapel, seemingly guarding this hidden gem.
In the afternoon, we sail along the southern coast of Sifnos, admiring the picturesque coves that add to the island’s charm, until we reach Faros, a quaint fishing village. From here, we can visit Kastro, one of the most delightful and iconic villages on the island.
Kastro is a captivating medieval village perched on a hill. Its ancient whitewashed houses, built in the Cycladic style, and cobblestone streets invite you to wander and lose yourself in its breathtaking views of the surrounding islands. Once fortified, the village offers enchanting vistas of the sea and preserves the atmosphere of a rich historical past, with archaeological remains and small churches scattered throughout.
In this place suspended between sea and sky, we stop for dinner at one of the traditional tavernas in Kastro. Here, we’ll savor the traditional dishes of Sifnos, surrounded by the village’s authentic ambiance. It’s a perfect opportunity to immerse ourselves in the local culture and flavors, creating a memorable evening in this enchanting Cycladic treasure.
Sailing to Despotico
THURSDAY:
A beautiful and fast sail takes us to Despotico, a wild and uninhabited island that comes alive with the arrival of boats from nearby Paros and Antiparos. Despotico is a place of rare beauty, where untouched nature and a serene atmosphere create a true sanctuary far from the world.
We anchor in the clear waters of the channel separating Despotico from Antiparos, a corner of paradise with transparent depths and landscapes that seem painted by an artist’s hand. The afternoon passes slowly, filled with refreshing swims and moments of relaxation onboard, surrounded by the silence and untamed beauty of this secluded haven.
As the sun begins to set, we prepare for an aperitif onboard, sipping drinks and marveling at the sunset painting the sky in warm hues. As the sun dips into the sea, the landscape transforms into a perfect canvas, providing a magical finale to our day in this unspoiled corner of the Cyclades.
We celebrate the evening with an iconic dish from Italian tradition: tagliatelle with ragù. Your skippers, with passion and expertise, knead eggs and flour to create fresh tagliatelle, while the ragù simmers slowly, releasing the authentic aromas of Italian cuisine. The result is a dish rich in flavor and warmth, a tribute to fine dining enjoyed in this breathtaking setting. This convivial dinner brings a touch of Italy to our journey, making the evening truly unforgettable.
Esplorazione di Despotico e Navigazione verso Paroikia
FRIDAY
The day begins with a visit to the archaeological park of Despotiko, a fascinating site that preserves ancient artifacts and tells the millennia-old history of this uninhabited island. After our exploration, a short but thrilling sail takes us to three small islets in the channel between Antiparos and Paros, where we anchor for a lunch break. Here, we indulge in moments of relaxation and refreshing swims in the crystal-clear waters that separate these islands.
In the afternoon, we set sail again to reach Paroikia, the capital of Paros. Along the way, we navigate through the narrow strait between Paros and Antiparos, a passage characterized by shallow waters and the vibrant presence of kitesurfers. Their colorful kites fill the sky, resembling flocks of butterflies dancing on the waves. This lively and dynamic display adds a unique charm to our journey.
SATURDAY
On Saturday morning, after a relaxing breakfast on board, it’s time to say goodbye. We conclude our adventure with disembarkation, taking with us the unforgettable memories of this cruise through the beauties of the Cyclades.
The stages of the itinerary are subject to change due to weather conditions or other unforeseen circumstances that prevent or make navigation to reach them or mooring uncomfortable. Any changes to the itinerary are implemented exclusively to ensure a better organization of the holiday and to ensure the safety and comfort of our guests.

