Western Cyclades Sailing Adventure

Destinations >> Greece >> Western Cyclades Sailing Adventure

Set sail on a captivating journey through the Western Cyclades. This adventure offers more than just stunning beaches and crystal-clear waters; it’s a deep dive into the rich history and vibrant culture of the Aegean. Begin your voyage exploring the diverse geography and abundant marine life of these enchanting islands. Marvel at the traditional Aegean architecture and savor Mediterranean cuisine at its finest.

Immerse yourself in local culture with guided tours and taste the unique flavors of each island. Engage in hands-on sailing, whether you’re a novice or an experienced sailor, under the expert guidance of our friendly skippers. This itinerary goes beyond mere island hopping, providing you with the opportunity to learn about the history and traditions of this beautiful region while enjoying the thrill of sailing in the deep blue Aegean waters.




This sample itinerary is just the beginning. Fully customizable for individuals, families, and groups of all sizes, let it serve as an inspiration for your next adventure. Price subject to change.


Explore the ancient ruins and bustling markets of Athens where the past blends seamlessly with the present, offering a taste of Mediterranean cuisine and culture.


Sail through tranquil waters, visiting islands ranging from serene Kythnos to the volcanic landscapes of Milos, each offering its own unique charm and beauty.


Swim in clear waters and visit the Temple of Poseidon, where the setting sun creates a peaceful atmosphere against the backdrop of ancient ruins.


Experience natural hot springs under the stars, enjoying a tranquil evening with views of the Milky Way and the soothing sounds of the sea.


Enjoy delicious Aegean seafood dishes in picturesque villages, savoring the fresh flavors of the region in a relaxed island setting.

Start your day with a leisurely stroll around the historic center of Athens or indulge in some last-minute shopping before heading to the marina. Here, you will board your sailing boat, your home for the next week. After settling into your cabin, the skipper will introduce you to the itinerary during a brief orientation.

In the late afternoon, set sail from the marina, taking in the scenic views of Athens’ southern suburbs. Your journey begins by heading east towards Cape Sounion, home to the iconic Temple of Poseidon. Perched high on a cliff, this ancient landmark overlooks the dark blue waters and is a testament to both ancient and modern marvels.

Your destination for the night is the island of Kythnos, the gateway to the Aegean archipelago. Kythnos offers a lively main town, a world-famous beach, and postcard-perfect views from the numerous chapels perched on the cliffs. Anchor at Kolona Beach, a stunning natural double bay divided by a strip of sand, and spend the night surrounded by the serene beauty of the Aegean.

Begin your day with breakfast and a refreshing swim in the crystal-clear waters of Kolona Beach. Afterward, snorkel towards the sea urchin colonies nestled in the cliffs on the southern side of the beach. For those feeling adventurous, take a short, easy hike up to a whitewashed chapel overlooking the Aegean. The centuries-old structure’s courtyard is now home to a small herd of wild goats, providing excellent photo opportunities.

Late in the morning, set sail southwards, leaving Kythnos behind as you head towards the island of Serifos. En route, take a leisurely swim in one of the many tiny bays dotting the island’s eastern side.

By early evening, dock at the marina and venture out to explore the main town, perched up the mountain. With its labyrinthine alleyways, numerous chapels and windmills, vibrant coffee culture, and breathtaking views of the southern archipelago, Serifos embodies the quintessential Greek island experience. Indulge in the freshest seafood right on the beach, a perfect way to end your day.

Begin your morning with a quick swim while the sailing boat is readied for another unforgettable journey.

Today, we sail towards Milos, an island renowned for its volcanic landscapes and unique geological formations. Enjoy stunning sunset views away from the crowds of Santorini, amidst lunar-like landscapes, vibrant nightlife, and exceptional local cuisine.

For meat enthusiasts, discover the island’s top spot for lamb or goat stew. Seafood lovers can indulge in fresh catches at Apollonia, a quaint fishing village with charming family-run tavernas by the water.

In the evening, take a local bus to the main town perched atop cliffs. Milos Town features traditional Cycladic architecture bustling with travelers and locals. Explore boutique cafes, bistros, restaurants, and delightful shops, ending your day with a cocktail on a balcony overlooking the Aegean, soaking in the essence of Milos.

Milos, a volcanic island, boasts stunning geological formations evident throughout its landscape. After breakfast, embark on a sailing excursion to two breathtaking swimming spots, starting with Kleftiko Beach on the southern tip. Once a pirate’s cove, Kleftiko mesmerizes with crystal-clear waters, sea caverns, and towering rock formations—a truly unique and picturesque setting. Glide through the caves aboard the dinghy, perfect for exploring and snorkeling amidst this natural wonder. Keep an eye out for Mediterranean dolphins, as music may attract them—don’t forget your playlists!

In the evening, return to Milos Marina, where you’ll have the remainder of the day to further explore the island. Your skipper is on hand to offer recommendations for activities, must-see sights, and guide you to authentic island dining experiences. Enjoy the freedom to immerse yourself in Milos’ charm and discover its hidden treasures at your own pace.

After breakfast, bid farewell to Milos as we sail northeast, passing through the straits of Kimolos. A short journey brings us to Polyaigos, a tiny, barren, uninhabited island known for its Mediterranean seal population. Keep an eye out for these seals as they hunt near their sea cavern homes. The south side of Polyaigos offers some of Europe’s most spectacular beaches, perfect for swimming and snorkeling. Explore the island further with hikes where you may encounter wild goats grazing by the sea.

In the evening, set sail north towards Sifnos. Our skipper’s favorite spot in the world awaits at the bay of Vathy on the island’s southern end. Spend the night here and indulge in the local cuisine at two family-run tavernas renowned for serving some of Greece’s finest meals. Enjoy dishes made with fresh vegetables straight from the garden, succulent goat or beef stews, and grilled lobster or mullets caught fresh from the sea—an unforgettable culinary experience.

After breakfast, bid farewell to Sifnos and set sail once again for Kythnos. Today’s route takes us along the island’s eastern side, pausing for a midday swim in a secluded bay south of Kythnos. Our destination is the charming fishing village of Loutra.

Upon arrival, unwind in the rejuvenating hot springs or indulge in a relaxing spa treatment, both offered at an incredible value of 6 euros per session. In the early evening, join our guide for a tour of the island’s main town, just a short drive away. The town captivates with its stunning traditional whitewashed houses, cobblestone streets, and quaint alleyways. Experience some of the finest meat-based dishes in the archipelago, alongside homemade delicacies like baklava and chocolate pies. Engage with friendly locals and embrace the relaxed pace of life that defines Kythnos.

After dusk, savor a cold, locally brewed beer by the water’s edge, or don your swimsuit and gaze at the Milky Way from the natural pools where the hot springs meet the sea—an enchanting end to your day on Kythnos.

Start your day with a cup of traditionally brewed coffee in the picturesque fishing village of Loutra. Then, bid farewell to Kythnos as we set sail towards the mainland and Cape Sounion, home to the iconic Temple of Poseidon.

We’ll anchor in one of the many bays near the cliffs where the temple stands proudly overlooking the Aegean Sea. Using the dinghy, we’ll disembark and hike to the temple, exploring one of the most significant archaeological sites in this part of the world.

In the late afternoon, we sail back towards the marina in Athens, making stops along the way for refreshing swims in the crystal-clear waters.

Upon arrival at the marina, your guide will escort you to the heart of Athens for a memorable farewell dinner in the historic center of Greece’s capital city, celebrating the end of an incredible sailing adventure through the Western Cyclades.

All too soon it's time to say goodbye to these magical islands. Depart the boat for the next leg in your journey. 

Accommodation in listed hotels or similar

Meals (B/L/D) as indicated

Private transportation in air conditioned vehicles

Activities as listed in the itinerary

Entrance fees

Expert local guide

International and domestic airfare

Optional tours, activities, and entrance fees not included in the itinerary

Personal items and services, i.e. portage, laundry, telephone, extra alcoholic drinks, medical expenses, etc.

Gratuities for drivers & guides

Travel insurance

How to book instructions

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