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Embark on an unforgettable adventure across the crystalline waters of the Aegean Sea, where each island is a chapter in a living epic, blending breathtaking nature, rich traditions, and the soul of ancient Greece. The Aegean Sea Sail & Hike Tour is not just a vacation—it’s an odyssey.
Sail from one storied island to the next, retracing the mythical routes of Odysseus and Jason, and discover Greece as few ever do: by sea, by foot, and through the eyes of its vibrant local culture. Each day brings new landscapes to explore—lunar coastlines, serene hilltop villages, untouched beaches—and new stories etched in stone, wind, and water.
Your journey begins in Athens, the heart of classical civilization. Here, ancient temples and bustling modern life exist in harmony. From the shadow of the Acropolis, your voyage begins with the thrill of anticipation and a warm Aegean breeze guiding you toward discovery.
Setting sail from the historic port of Lavrio, your floating home is a luxurious catamaran—your base for both comfort and exploration. Together, we journey through the Cyclades, a constellation of islands each with its own unique charm.
Wander the whitewashed alleys of Kythnos, hike through sun-kissed paths of Serifos, and bask in the culinary and cultural richness of Sifnos, famed for its traditional pottery and authentic cuisine. Marvel at the untouched beauty of Polyaigos, where electric blue waters meet blinding white sands, and experience the raw volcanic wonder of Milos, whose sea caves and striking rock formations have inspired artists and legends alike.
But this tour is not only about stunning vistas—it’s about deep connection. With every step and sail, you’ll engage with Greek island life at its core: sharing meals in family-run tavernas, learning local traditions, and soaking in stories that date back millennia. Meals are more than sustenance—they’re celebrations of Mediterranean abundance, from fresh seafood and sun-ripened vegetables to hand-rolled pastries and golden olive oil.
Evenings are marked by laughter, sea breezes, and star-filled skies. And as each day fades into twilight, you’ll find yourself transformed—by the land, the people, and the shared rhythm of sailing, hiking, and discovering.
In Greece, the destination is just the beginning. This is a voyage through history, culture, and nature, woven together in a once-in-a-lifetime experience that lives on long after your feet have left the sand.
Highlights:
Sailing the Iconic Cyclades on a Luxurious Catamaran
Cruise through the heart of the Aegean aboard a spacious, elegant catamaran—your floating home as you explore both celebrated and hidden islands.
Immersive Hikes Through Whitewashed Villages and Ancient Trails
Trek scenic paths on islands like Kythnos, Serifos, and Sifnos, where every stone holds a story—from Byzantine chapels to panoramic ridgelines.
Swim in the Turquoise Waters of Polyaigos
Experience the surreal beauty of Polyaigos, an uninhabited island of blinding white cliffs and crystal-clear seas, perfect for snorkeling and serenity.
Discover Myth-Laden Islands
Walk in the footsteps of Greek heroes, exploring islands steeped in mythology—from the legends of Medusa to the birthplace of Aphrodite’s statue.
Culinary Journeys through Traditional Greek Flavors
Savor fresh, authentic meals in local tavernas and onboard, with dishes crafted from sun-kissed produce, just-caught seafood, and centuries-old recipes.
Blend of Culture, Nature, and Local Life
This is more than a sightseeing tour—connect with local artisans, unwind in family-run eateries, and gain a deeper understanding of the Greek island way of life.
Moderate (Hiking)
We curated this experience for people who enjoy trekking. You should be in good physical condition. The walking trails are a mixture of dirt tracks and well-constructed stone mule paths. Along the coast, we walk on the sand for some stretches — a good walking pole may be useful. Relatively easy hikes, 3 to 5 hours per day. This a good start for a first trekking holiday.*
*If you don’t want to hike, you can just hang out on the boat or enjoy the warm Aegean waters.
Sailing
No sailing experience necessary. Those who are already familiar boating are more than welcome to assist our certified skipper throughout the journey. This trip is also a great opportunity for people with no experience to learn the fundamental principles of the art of sailing.
Your adventure begins in Athens, the birthplace of democracy, drama, and philosophy. Upon arrival, settle into your centrally located hotel—just a stone’s throw from ancient wonders. In the evening, join your guide for a relaxed walking tour through Plaka, the oldest neighborhood in Athens, where time seems to slow between neoclassical facades and cobbled lanes.
Later, enjoy a festive welcome dinner in a traditional taverna tucked beneath the glowing Acropolis. Dine like Athenians do—with shared plates, flowing wine, and stories that stretch back centuries.
Overnight in Athens (D)
Start your day with a hearty Greek breakfast, then delve into the wonders of ancient Athens. Stand atop the Acropolis, where gods once walked and philosophers shaped the world. Admire the majestic Parthenon, the Temple of Athena Nike, and the sweeping views of the city below. Continue to the Acropolis Museum, home to marble masterpieces and relics of divine legends.
Lunch at the museum’s elegant terrace restaurant offers panoramic views of what you’ve just explored. Then, transfer to the port of Lavrio, where your luxurious catamaran awaits. As the sails catch the wind, leave the city behind and drift toward Kythnos, the island of hot springs and hidden coves—beloved by the ancients and relatively untouched by modern crowds.
Sailing distance: ~25 nautical miles / Duration: Approx. 3-4 hours
Overnight in Kythnos (on board) | B, L, D
Wake to the gentle lapping of the sea and enjoy breakfast on deck. This morning’s hike takes you through the Chora of Kythnos, a charming maze of whitewashed houses, blue shutters, and blooming geraniums. Explore sleepy squares, quiet chapels, and panoramic trails where the scent of thyme and sage fills the air.
Pause for a rustic lunch in a traditional taverna, tasting the local cheeses and sun-dried tomatoes Kythnos is known for. In the afternoon, set sail once more, this time to Serifos, the island where Perseus is said to have turned the wicked king Polydectes to stone with the head of Medusa.
Sailing distance: ~30 nautical miles / Duration: Approx. 4-5 hours
Overnight on board | B, L, D
After breakfast, begin your ascent through the Chora of Serifos, perched dramatically on a hillside like a crown of white jewels. The hike is both scenic and symbolic, passing age-old paths and Byzantine chapels. From the top, gaze out over olive groves, windmills, and the shimmering Aegean.
According to myth, Serifos was the childhood refuge of Perseus and his mother Danaë after being cast into the sea in a chest. The island’s rough beauty mirrors its legendary past.
Later, continue to the serene shores of Sifnos, an island of refined simplicity, known for its gastronomic excellence, traditional pottery, and network of ancient footpaths.
Sailing distance: ~12 nautical miles / Duration: Approx. 2 hours
Overnight on board| B, L, D
After several active days, today offers a slower rhythm. Spend your morning basking on a quiet beach or wandering through the peaceful village of Apollonia, named after the god of light himself. For the more adventurous, an optional hike takes you along cobbled trails to medieval monasteries, olive groves, and secluded coves.
Sifnos is also the birthplace of Nikolaos Tselementes, the chef who revolutionized Greek cuisine. In the evening, consider sampling revithada (slow-baked chickpeas) or mastelo (marinated lamb with dill and wine) at a local taverna.
Overnight on board
Sail: 2-hours | Hike 4.5-hours | B, L, D
Today’s destination is a hidden paradise: the uninhabited island of Polyaigos, meaning “many goats.” With no roads, no villages, and no crowds, this is pure Cycladic wilderness. Often called the “Maldives of Greece” for its surreal blue waters and brilliant white cliffs, Polyaigos offers some of the clearest snorkeling in the Mediterranean.
Swim in translucent coves, sunbathe on untouched beaches, and feel like the only soul in the world. In the distance lies Kimolos, a quiet island known for its chalk cliffs and calm, nostalgic charm.
Sailing distance: ~30 nautical miles / Duration: Approx. 3-4 hours
Overnight on board| B, L, D
Your final full day is nothing short of spectacular. Sail to Milos, a volcanic island sculpted by fire and water. Milos is where the iconic Venus de Milo was discovered, a symbol of classical beauty now housed in the Louvre.
Cruise past the island’s otherworldly rock formations, hidden beaches, and sea caves, including the famous Kleftiko, once a pirate hideout. Swim and snorkel in turquoise waters, and soak in the strange, stunning colors of Milos’ dramatic landscape.
Sailing distance: ~7 nautical miles / Duration: Approx. 1 hour
Overnight in a luxury resort in Milos| B, L, D
Before leaving Milos, there’s time (optional) for one final immersion into its timeless spirit. Start your morning with a choice of experiences: embark on a short hike through the island’s scenic inland paths—tracing ancient stone terraces, white chapels, and sweeping sea views—or explore the Catacombs of Milos, an extraordinary archaeological site carved into volcanic rock and once used by early Christians as sacred burial chambers.
After this final taste of island history and beauty, we take a short flight back to Athens, where the city’s eternal heartbeat welcomes you once more. The afternoon is yours—perhaps for a relaxed stroll in the National Gardens, some last-minute shopping in Monastiraki, or a sunset toast at a rooftop café with a view of the Acropolis.
Flight duration: 45′ – Overnight in Athens | B, L
Your Aegean journey may end, but the echo of the islands will call you back again and again.
After one last leisurely breakfast, your Aegean Sail & Hike Tour officially concludes. Whether you’re heading home or extending your time in Greece, you’ll carry the stories, flavors, and breathtaking landscapes of the Aegean Sea with you.
But the adventure doesn’t have to end here..
You can choose to explore more of Athens, or continue your travels to other iconic Greek destinations. Aegean Outdoors offers a variety of tailor-made extensions throughout Greece, including Crete, Mount Olympus, Meteora, Northern Greece, and Peloponnese adventures. Whether you seek more hiking, cultural immersion, or coastal relaxation, we’re here to plan your next chapter.
Until then—”kalo taxidi” (safe travels)!
Price is based on a minimum attendance of 6 people (for less or more participants, please to contact us. End of July-August prices may vary).
Greece enjoys a Mediterranean climate, with warm sunny days and occasional cool breezes, especially on the islands or at higher elevations. The best approach to packing is to use the layering system—this allows you to easily adjust to changing temperatures. If it gets hot, you can remove layers; if it turns windy or cooler, you can quickly layer up for comfort.
Travel light, travel smart. The less you carry, the easier your journey will be—especially when navigating ferry ports, cobblestone streets, or compact sailboats. Minimalist packing isn’t just convenient at the start; you’ll thank yourself at the end of the trip, too.
Here’s a list of recommended items to bring on your Aegean Sea Sail & Hike Tour:
*This packing list is meant to serve as a flexible guideline, not a strict checklist. Feel free to adapt it based on your personal preferences, travel style, and the specific activities you have planned. Add what you need, skip what you don’t—the goal is to pack smart and travel comfortably.