We meet in Athens and transfer to Lavrio port, stopping for lunch before setting sail to the island of Kythnos. Our boat becomes our home for the week as we journey into the Cycladic blue. After a four-hour sail, we arrive in Kythnos, where we anchor in the serene bay of Apokrousis. Dinner is served on board, under a sky full of stars.
Overnight in Kythnos
Lunch and dinner included
Driving distance: Athens to Lavrio 60 km / 1 hr
Sailing time: Lavrio to Kythnos 4 hr
After a hearty breakfast, we set off for the whitewashed village of Dryopida, nestled in the heart of Kythnos. This quiet island, one of the lesser-known gems of the Cyclades, is prized for its thermal springs, unspoiled beaches, and simple island charm. From Dryopida, our scenic hike begins—winding through vineyards, low hills, and small chapels as we make our way toward the seaside village of Kanala. The trail offers sweeping views of the Aegean and leads us to a peaceful cove for a refreshing swim. Back on board, we enjoy a relaxed lunch as we set sail for Sifnos, an island beloved for its harmonious landscapes, stone-paved villages, and strong culinary tradition. Tonight, we dine at a charming local taverna, tasting flavors rooted in the island’s long-standing food culture.
Overnight in Sifnos
Breakfast, lunch and dinner included
Hiking duration: 3 hr
Sailing time: Kythnos to Sifnos 5 hr
We begin the day with a hike from Apollonia, following scenic trails through the elegant villages of Artemonas and Kastro —known for their Cycladic charm and well-preserved architecture. Along the way, we visit Panagia Poulati, a striking seaside chapel nestled against the rocks, and continue through the green valley of Erkies toward Kato Petali. After lunch at a local taverna, surrounded by the sounds and smells of village life, we make our way to the coast near Chrissopigi. There, our boat awaits for an afternoon sail to Milos. We arrive in time for a swim in its deep blue waters and a relaxed dinner on deck, as the cliffs of the island glow in the afternoon light.
Overnight in Milos
Breakfast, lunch, and dinner included
Hiking duration: 4 hr
Sailing time: Sifnos to Milos 2 hr
This morning’s hike begins in the colorful village of Klima, with its iconic syrmata—boat garages painted in cheerful hues—and climbs through Tripiti to the ruins of ancient Milos. Here, we explore early Christian catacombs and a hillside Roman theater with sweeping Aegean views. Famous for the Venus de Milo, the island’s layers of history and surreal volcanic terrain continue to inspire.
We stop for lunch in the hilltop village of Plaka before heading to the port. In the afternoon, we sail to Kimolos or the uninhabited shores of Poliegos—home to some of Greece’s clearest waters and quietest coves. The rest of the day is all about the sea: swimming, sunbathing, and soaking in the calm beauty of the Aegean.
Overnight near Kimolos or Poliegos
Breakfast, lunch and dinner included
Hiking duration: 4 hr
As we begin our journey northward through the Aegean, gradually sailing back toward Lavrio, we return to Sifnos for one final hike—one of its most scenic. The trail leads from the lively village of Apollonia down to the tranquil bay of Vathi. Along the way, ancient stone walls, hillside chapels, and sweeping sea views frame our descent. After a refreshing swim and lunch by the water, we sail to Serifos.
We arrive in the afternoon and make our way up to its striking Chora, perched dramatically on a rocky peak. With its narrow alleys, whitewashed houses, and breathtaking views over the sea, it’s one of the most captivating villages in the Cyclades. Tonight, we’ll enjoy dinner at a traditional local taverna.
Overnight in Serifos
Breakfast, lunch and dinner included
Hiking duration: 4 hr
Sailing time:
Kimolos to Sifnos 2 hr
Sifnos to Serifos 2 hr
Today we hike a loop trail that explores the untamed hinterland of Serifos. Passing through ruined farmsteads, Byzantine chapels, and windswept hillsides, we get a true taste of wild Cycladic beauty. Serifos is steeped in myth—according to legend, it was here that Perseus returned with the head of Medusa, turning the island's tyrant king to stone and freeing his mother from captivity. In later centuries, Serifos became known for its rich deposits of iron and copper, and remnants of its mining heritage still mark the landscape. After the hike, we head back to the boat and sail to Kythnos for a refreshing swim in its warm waters.
Overnight in Kythnos
Breakfast, lunch and dinner included
Hiking duration: 4 hr
Sailing time: Serifos to Kythnos 3 hr
We start the day with a final swim in the warm, mineral-rich waters of Loutra Bay, long valued by locals for their soothing, healing qualities. Then we set sail across the northern Aegean, slowly making our way back toward the mainland. Before reaching port, we pause at Cape Sounion to visit the majestic Temple of Poseidon, standing watch over the sea since the 5th century BCE.
This ancient sanctuary once marked the last sight of home for sailors leaving Attica and the first welcome for those returning. With sweeping sea views framed by its marble columns, it offers a quiet moment to reflect on our journey. Our final dinner is in the harbor town of Lavrio, a place steeped in maritime history and the perfect ending to our time in the Aegean.
Overnight in Lavrio (onboard)
Breakfast, lunch and dinner included
Sailing time: Kythnos to Lavrio 4.5 hr
After breakfast, we transfer to the airport or continue your journey independently. Wherever you go next, may the wind stay at your back and may the memories of the Cyclades carry you forward.
Breakfast included
Driving distance: Lavrio to Athens airport 36km / 45 min
We are constantly updating our unique itineraries based on new information and experiences available. The walks, accommodations, and visits listed may be adjusted. The itineraries presented are subject to modification and change by Tripin Adventures. We reserve the right, without penalty, to make changes in the published itinerary whenever, in our judgment, conditions warrant, or if we deem it necessary for the comfort, convenience, or safety of participants, anything not mentioned in above program.
