Sail and Hike

Upon arrival in vibrant Athens, settle into your hotel and take some time to relax. In the evening, meet your guide for a leisurely walking tour through the historic center, soaking in the charm of Plaka — the old town nestled beneath the Acropolis. Cap the day with a traditional Greek dinner at a taverna with breathtaking views of the illuminated Parthenon. (B)
Overnight in Athens

Start the day with a guided tour of Athens’ top landmarks: the Acropolis and Parthenon, the ancient Panathenaic Stadium, where the first modern Olympics were held in 1896, and the award-winning Acropolis Museum. After lunch at the museum’s restaurant, you’ll board a high-speed ferry to Serifos, the gateway to your sailing and hiking journey. Upon arrival, hike through the iconic Chora — a dazzling hilltop village — and make your way to Psili Ammos, one of the island’s most stunning beaches. Here, your catamaran awaits. After settling into your cabin, enjoy your first dinner on-board.
Ferry Piraeus to Serifos: 2-hours | Hike: 3.5-hours | Overnight on-board, Serifos | (B,L,D)

Early in the morning, we set sail for Milos, a striking volcanic island in the southwestern Cyclades. Milos is world-renowned as the discovery site of the Venus de Milo (Aphrodite), a masterpiece of ancient Greek sculpture now housed in the Louvre Museum in Paris.

Our catamaran docks at the charming fishing village of Pollonia, the starting point for today’s hike. Along the trail, we’ll explore the surreal, moon-like landscape of Sarakiniko, the sea-carved caves of Papafragas, and the archaeological site of Filakopi — once one of the most significant prehistoric settlements in the Aegean.

The hike concludes at the picturesque beach of Mandrakia, where white sands and turquoise waters invite us for a refreshing swim. Later, the catamaran sails to Adamas Bay, home to the largest natural harbor in Greece and one of the safest anchorages in the Mediterranean. In the evening, we’ll explore the lively town of Adamas and enjoy dinner at a traditional local taverna.
Sail 4.5-hours | Hike: 4-hours | Overnight on-board, Adamas Bay |(B,L,D)

Today’s sailing trip around the island takes us to picturesque beaches, inviting sea caves, rare and extraordinary geological formations, and stunning hidden spots accessible only by boat. We’ll visit the spectacular rock formations of Glaronissia, Arkoudes, Sikia, and Kleftiko. Enjoy swimming and snorkeling in turquoise waters, and soak up the Greek sun and sea!

In the evening, we’ll sail to either Kimolos or Polyaigos to anchor for the night in preparation for the next day’s departure. Lunch will be served on board. Dinner will be either on board or at a local tavern in Kimolos. Overnight on board, Kimolos or Polyaigos (B,L,D)

Next stop of our Cycladic Odyssey is the island of Sifnos, one of the most enchanting and well-rounded Greek islands. Known for its beautiful beaches, idyllic villages, and a wide variety of scenic hikes, Sifnos offers something for everyone—and we’ve selected one of the very best.
Our vessel will dock at Platys Gialos, the starting point of today’s hike. This walk takes us far from modern civilization, immersing us in the island’s natural beauty and timeless charm.
What better way to end the day than with a fantastic Greek dance lesson experience?
Overnight on-board / Sail: 2-hours | Hike 4.5-hours | (B,L,D)

Our hike this morning begins in Kastro, the ancient capital of Sifnos and one of the best-preserved settlements in the Cyclades. From there, we head toward Apollonia, the island’s modern capital, known for its cosmopolitan charm, bustling shops, cozy cafés, and traditional tavernas. We’ll stroll through its narrow streets, admire beautiful architecture, and visit some of its remarkable churches.

From the heart of town, we venture into Skafi, a hidden valley rich with history and natural beauty. Home to ancient monasteries, mysterious caves, and breathtaking views from the Church of Panagia tou Niliou, known as the “Aegean Balcony,” it’s the perfect setting for a relaxing picnic lunch.

The hike continues to Mavro Chorio (“Black Village”), famous for its stone huts, impressive terracing, and unique gates. Our trail leads to the spring of Kalamitsi, nestled between two towering crags known as the Froudia Baronas. Atop the larger crag stands an ancient citadel, echoing tales of Sifnos’ distant past.

We then begin our descent to the Bay of Vathy, arguably the island’s most stunning beach village, where our catamaran awaits. Time for a refreshing swim and, to end the day on a delicious note, a marvelous cooking class on board!
Hike: 6-hours / Overnight on board | (B,L,D)

Kythnos, our next island destination, is a hidden gem of the Western Cyclades – known for its authenticity, raw beauty, and traditional charm. With its whitewashed villages, rolling hills, and more than 70 beaches, Kythnos offers a serene escape untouched by mass tourism.
Our destination is Kolona Beach, one of the most iconic and photographed beaches in Greece. This natural wonder is a narrow strip of golden sand connecting the main island to the islet of Agios Loukas, creating a unique double-sided beach with crystal-clear waters on both sides. Surrounded by wild, unspoiled landscapes and gently sloping hills, Kolona is the perfect place to swim, relax, and bask in the tranquility of the Aegean sun.
This beach has long been admired not just for its beauty, but also for its peaceful setting—once a natural harbor for ancient sailors and now a quiet haven for those seeking a true Cycladic escape.
Sail: 5.5-hours | Overnight on board | (B,L,D)

After a delightful breakfast on board, we set off by private motor coach or taxis to the Chora of Kythnos, the island’s main village and a classic example of Cycladic architecture. With its maze of narrow alleys, whitewashed houses, blooming bougainvillea, and blue-domed chapels, Chora is as picturesque as it is peaceful. Our hike begins here, just after a brief exploration of the village and a visit to Panagia tou Nikous, a revered church that offers insight into the island’s deep-rooted spiritual traditions.
This exceptional trail is considered one of the most scenic hikes in the Cyclades, taking us along ancient footpaths paved with large flat stones and offering panoramic views of the surrounding Aegean Sea and neighboring islands. We pass terraced hillsides shaped by generations of farmers and shepherds, and make our way to Agios Georgios, a quiet settlement leading to the unspoiled, sandy beach of Agios Ioannis. Remote and serene, this beach feels like a secret corner of the Aegean, perfect for a peaceful pause.
Our loop trail eventually brings us back to Chora, where we will be transferred back to our boat, ready for our final sail—an unforgettable voyage to Cape Sounio on the mainland.
Here, perched dramatically atop a rocky cliff that plunges into the sea, stands the majestic Temple of Poseidon, one of ancient Greece’s most iconic sanctuaries. Built in the 5th century BCE to honor the god of the sea, the temple offers commanding views over the Aegean. As the sun sets behind the marble columns, casting golden hues over the headland, you’ll understand why this place has stirred poets and travelers for centuries.
We’ll enjoy a picnic lunch during the day and gather for a farewell dinner beneath Poseidon’s watch—either on board or at the elegant Grecotel Cape Sounio Hotel. A perfect closing chapter to a journey filled with discovery, beauty, and unforgettable moments.
Sail: 3.2-hours | Hike: 3.5-hours | Overnight on board | (B,L,D)

Enjoy a final breakfast on board as we sail along the beautiful Athenian Riviera, a stretch of coastline known for its elegant seaside suburbs, sparkling bays, and historic charm. Our journey concludes at Alimos Marina, one of Athens’ major harbors and a gateway between city life and the open sea.
End of services—but the memories made under the Aegean sun will sail with you forever.
Sail: 3-hours | B