Discover the Cyclades

Explore the Enchanting Island World of the Cyclades aboard the Sea Cloud


Revel in the blue and white Greek idyll of the Cyclades! Aboard the majestic windjammer Sea Cloud, spend a week island-hopping under sail in the blue Aegean, visiting some of the archipelago's most enchanting isles. Your stops include Astypalaia, an off-the-beaten-path island with enticing beaches and white-washed houses with red windmill roofs, Amorgos, an island of golden beaches and crystal-clear waters, and Naxos, with its fishing villages and old Venetian castle. Along the way you'll step into the past as you visit the most impressive Aegean monasteries: the brilliant white rock monastery of Panagia Hozovitissa on Amorgos and St. John's Monastery on Patmos, almost one thousand years old! Thanks to half-day layovers, you'll have extra time to sail and enjoy the authentic windjammer atmosphere. A renowned lecturer accompanies the trip and entertains with exciting talks and stories about the destination.

Note: This cruise is not exclusive to, nor operated by, Wilderness Travel, who acts solely as agent in booking your reservation with the ship operator. The itinerary, lecturers, and all other arrangements are subject to change at the discretion of the cruise line.


Day 1
Athens / Piraeus

"A ship will come...", declared the singer Melina Mercouri to the port of Piraeus. Later, as Greek Minister for Culture, she made Athens the first European Capital of Culture in 1985. The city is considered the birthplace of Europe, of philosophy and of democracy, and is the embodiment of the Olympic ideal. World-famous and a UNESCO World Heritage Site since 1987, its landmark is the magnificent Parthenon temple, lying high up on the Acropolis in all its glory. At the foot of the Acropolis hill is the Plaka, the oldest quarter of Athens, and the world's most modern archaeological museum, the new Acropolis Museum, has been here since 2009. Arrive in Athens and embark on the Sea Cloud, with a departure at 5:00 pm.

Day 2
At Sea

Climbing the rigging, untying ropes, setting sails—today is all about sailing. Time to lean back and relax in the deck chair and watch the passionate crew hoisting the sails by hand.

Day 3
Patmos / Dodecanese

The idyllic little island of Patmos houses one of the most important monasteries of the Greek Orthodox church. The monastery of St. John is a World Heritage Site, protected by UNESCO. It was built in honor of the Apostle John, who is said to have lived in a cave on the island. It is also said that he wrote down his Revelation of the Apocalypse there. The whole island is considered holy ground and is one of the most important pilgrimage sites in the Greek Orthodox world.

Day 4
Astypalaia / Dodecanese

Does it still exist, a real insider tip in Greece? Astypalaia seems to be one of these places that have become rare. From above, the small island jewel looks like a butterfly that has landed on the blue waters of the Aegean Sea. Since the journey to Astypalaia is a bit tedious—if you are not just relaxed with the windjammer on the way—the little island is spared from tourist crowds and has been able to preserve its original charm. Thus, between countless beaches, crystal clear water, snow-white alleys, and red windmill roofs, even as a guest you quickly become part of the typical Greek island everyday life.

Day 5
Amorgos / Cyclades

Amorgos is a beautful island of gorgeous beaches and impressive monasteries, including the gleaming white edifice of Hozoviotissa, dating back to the 11th century. Built on the edge of a cliff, it offers sweeping views of the blue Aegean. In the center of the island is the town of Chora, with its inviting squares, whitewashed houses draped by bougainvillea, picturesque alleys, and a 13th century Venetian castle (kastro). Amorgos was the setting of the 1988 film The Big Blue, starring Jean Reno.

Day 6
Naxos / Syros / Cyclades

In the south of Naxos lies the idyllic fishing village of Agia Anna, with its secluded tavernas and beach bars on the small promenade. On both sides, lovely bays and beaches entice you to swim in the crystal-clear water. The huge Venetian castle in the island's capital, only a few miles away, once protected the city from attackers. Nowadays it offers you a stunning view over the whole island in all its glory. Even the gods loved the island. The German opera "Ariadne auf Naxos" was based on the myth of Dionysus and the Cretan king's daughter. Later in the early evening, arrive at Syros for overnight.

Day 7
Syros / Cyclades

Although the capital of the Cyclades is situated on the tranquil and traditional island of Syros, outside of the town this seems the most remote island of them all. Ermoupoli, one of the most beautiful island towns in Greece, was built majestically on two hills. Its architecture is exceptional and the numerous monumental neo-classical buildings give the impression of a large, elegant town. Passing over the hill, the spaciousness and vastness transform into a maze of lanes and give a medieval impression.

Day 8
Piraeus / Athens

Arrive in Piraeus early in the morning and disembark at 9:00 am.



Discover the lesser-known Cyclades islands and their secrets, far from the tourist crowds
Explore the brilliant white rock monastery of Panagia Hozovitissa on Amorgos and St. John's Monastery on Patmos, almost one thousand years old
Enjoy leisurely strolls through charming little island capitals


Length: 8 days
Cost From: $6165  
Arrive: Athens, Greece
Depart: Athens, Greece
Lodging: 7 nights aboard a 64-passenger vessel
Meals: All meals aboard ship, including wine, beer, and soft drinks with lunch and dinner
Activity: Small Boat and Yacht Cruising, Archaeology, Cultural Adventures, Walking, Small Ship Cruising
Trip Level:

7-day cruise, cultural explorations and walking tours