Sailing Cyclades from Milos to Paros
Sail Adventure
Fast sailing and gourmet cuisine in the Western Cyclades
We’ll depart from Milos, a stunning Greek island in the Cyclades, offering breathtaking scenery, crystal-clear bays, and a charming Cycladic village. Nearby, we’ll visit one of our favorite stops, Polyaigos, an uninhabited island accessible only by sea. Here, we’ll drop anchor in a cove where the boat will seem suspended in mid-air, thanks to the incredibly clear water.
We’ll then sail to Paros, enjoying fast, fun cross-wind and close-hauled sailing. Aboard the Walkabout, a fast, ocean-going cruiser, stable and perfect for the intense conditions of the Aegean, every crossing will become an exciting adventure.
Our itinerary includes stops on other splendid islands, each with its own extraordinary and unique beauty. We’ll stop at Kimolos, a small, quiet island where the authenticity of Greek life is revealed among the narrow streets of the picturesque village of Chorio, rich in charm and tradition.
In Sifnos, we’ll drop anchor in the picturesque Pirates’ Bay, once a hidden haven for boats. While in Sifnos, a visit to the medieval Kastro, a fortified village with breathtaking sea views and centuries of history, is a must.
Antiparos is an island of great charm, with an elegant village full of boutiques and traditional shops. Here, we’ll have the opportunity to explore the Despotiko Archaeological Park, located on a nearby islet and home to important ancient finds. Here, the turquoise sea and rocky landscape blend together, creating a captivating atmosphere.
Each island is a discovery in itself, ready to reveal the best of Cycladic nature and culture, making our trip a true immersion in the authentic beauty of the Cyclades Islands.
This holiday is ideal for those seeking an unforgettable experience that combines the thrill of fast sailing with relaxation in pristine bays, where you can immerse yourself in nature and enjoy the sea.
On board, your experienced skippers will not only manage the boat but also prepare delicious meals, offering you the pleasure of fine dining in an unparalleled natural setting. This is the perfect holiday for those who love the sea, sailing, and the charm of the authentic Cyclades!
Itinerary
Embarkation and Welcome to Milos - Exploring Kleftiko: A Day Between 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, an aperitif with a welcome toast introduces us to the spirit of conviviality and relaxation that will characterize our cruise. Afterward, everyone will settle into their cabins and familiarize themselves with the boat. The evening offers the perfect opportunity to enjoy the lively atmosphere of the marina and get to know your fellow travelers better, letting the excitement for the days to come begin to sink in.
SUNDAY:
After leaving the large bay of Milos, we sail about ten miles with a tailwind until we reach the southwestern tip of the island, home to the spectacular Kleftiko. This fascinating place is known for its imposing rock formations: tall sea stacks emerge from the water, and the coast is dotted with mysterious caves that, according to legend, once offered refuge to pirates.
We’ll anchor on a white sandy seabed, immersed in crystal-clear waters and surrounded by enchanting cliffs. Here, the white rock is crisscrossed with fascinating veins of red, green, and yellow, a true natural spectacle that makes Kleftiko one of the most evocative landscapes in the Cyclades.
We’ll explore the caves aboard the dinghy, venturing into the ravines with a flashlight. The light illuminates the rock walls, revealing surprising colors and plays of shadow that make the exploration even more evocative. Every crevice seems to hold a secret, offering a unique and unforgettable experience in this corner of wild and fascinating nature.
The afternoon will pass peacefully, with dips in the clear waters and strolls along the long white beach. Relaxing on board becomes even more magical at sunset, when the cliffs are tinged with warm, enveloping colors, transforming the landscape into a living painting.
We’ll conclude the day with dinner on board and spend the night anchored in the bay, lulled by the sea and surrounded by the wild beauty of Kleftiko.
Exploration and Navigation to Polyaigos
MONDAY:
The day begins with a special stop to admire the spectacular sand falls, a fascinating natural phenomenon where sand slides down the rocks like a waterfall, creating a unique and evocative landscape. After this break, we set sail for a close-hauled sail that, depending on the wind, can prove intense and challenging, heading towards our next destination: Polyaigos, a wild and uninhabited island.
Upon reaching the island, we anchor in one of the most beautiful bays in the Cyclades, a true natural pool with crystal-clear waters and white sand, perfectly sheltered from the Meltemi winds. Here, an afternoon of pure relaxation awaits us: refreshing swims and time to enjoy the island’s pristine beauty.
At sunset, we’ll climb a mountain path for a short walk, where we’ll admire an unforgettable spectacle as the sun sets on the horizon, painting the sky with warm, enveloping colors.
The day concludes with a gourmet dinner on board, prepared by your skippers, who will transform the evening into a special culinary experience. We will sleep anchored in this deserted bay, lulled by the silence and magical atmosphere of Polyaigos.
Exploring Polyaigos and Sailing to Kimolos
TUESDAY
We continue our exploration of Polyaigos. This uninhabited and wild island of the Cyclades once again offers spectacular views and evocative landscapes of rare beauty.
In the afternoon, we set sail for nearby Kimolos, an authentic and welcoming island, where you’ll feel like you’ve dived into traditional Greece. Once there, we’ll visit the picturesque village of Chorio, with its whitewashed houses, narrow streets, and tranquil atmosphere that invites you to slow down and enjoy every detail.
The evening concludes with dinner at a typical local taverna, where we’ll savor traditional, authentic Greek cuisine while enjoying the pleasant, relaxed atmosphere of Kimolos.
Sailing and Discovery of Sifnos
WEDNESDAY
After an intense upwind sail, we land in a secluded bay on the southern coast of Sifnos, an island known for its authentic beauty. This narrow bay, accessible only by sea, is a magical and peaceful place, dominated by a solitary white house with a small church, seemingly guarding this hidden corner.
In the afternoon, we sail along the southern coast of Sifnos, admiring the picturesque coves that make the island so charming, until we reach Faros, a quaint fishing village. From here, you can reach Kastro, one of the most delightful and iconic villages on Sifnos.
Kastro is a charming medieval village perched on a hill, with its ancient white houses built in the Cycladic style and cobbled streets that invite you to wander and lose yourself among the alleys and breathtaking views of the surrounding islands. The once fortified village offers picturesque views of the sea and still retains the atmosphere of a rich history, with archaeological remains and small churches dotted around.
In this place seemingly suspended between sea and sky, we’ll stop for dinner at one of Kastro’s typical tavernas, where we’ll savor traditional Sifnian dishes. Surrounded by the authentic atmosphere of the village, we’ll immerse ourselves in the local culture and flavors.
Sailing to Despotico
THURSDAY
A beautiful, fast sail takes us to Despotico, an uninhabited and wild island, yet lively thanks to the boats arriving from nearby Paros and Antiparos. Despotico is a place of rare beauty, where unspoiled nature and a tranquil atmosphere create a true refuge from the world.
We drop anchor in the clear waters of the channel separating Despotico from Antiparos, a corner of paradise with transparent seabeds and landscapes that seem like paintings. The afternoon passes slowly, with refreshing swims and moments of relaxation on board, lulled by the silence and wild beauty of this place.
As the sun begins to set, we prepare for an aperitif on board, sipping a drink and admiring the spectacular sunset that paints the sky with warm hues. As the sun dips into the sea, the landscape transforms into a picture-perfect canvas, providing a magical end to our day in this pristine corner of the Cyclades.
We’ll celebrate the evening with an iconic dish from the Romagna tradition: tagliatelle with ragù. Your skippers, with passion and skill, knead eggs and flour to create fresh tagliatelle, while the ragù slowly simmers, 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. A convivial dinner that brings a touch of Italy on board, making the evening unforgettable.
Exploration of Despotico and Sailing to Parikia
FRIDAY
The day begins with a visit to the Despotico Archaeological Park, a fascinating site housing ancient artifacts and revealing the millennia-old history of this uninhabited island. After exploring, a short but intense sail takes us to three islets in the channel between Antiparos and Paros, where we drop anchor for lunch. Here, we enjoy another moment of relaxation and refreshing swims in the clear waters separating these islands.
In the afternoon, we resume sailing to reach Parikia, the capital of Paros. Along the way, we cross the narrow passage between Paros and Antiparos, a stretch characterized by shallow waters and the lively presence of kitesurfers, whose colors fill the sky and resemble flocks of colorful butterflies dancing on the waves. This spectacle of energy and movement lends a unique atmosphere to our passage.
SATURDAY
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 beauty of the Cyclades.
The itinerary is subject to change due to weather conditions or other unforeseen circumstances that prevent or make it difficult to reach or dock the destination. Any changes to the itinerary are made solely to ensure a better organization of the holiday and to ensure the safety and comfort of our guests.