Cruising the Greek Isles

Exploring the Aegean Islands aboard the Sea Cloud


Set a course for picturesque islands and mythical ruins! Aboard the beautiful windjammer Sea Cloud, the legendary former private yacht of Marjorie Merriweather Post, you'll sail the lesser-visted isles of the Cyclades to discover the gems of the Aegean Sea. On the Peloponnese Peninsula, you'll walk into the past at Mycenae, one of the major centers of Greek civilization in the second millennium BC, and see the 14,000-seat theater at Epidaurus. As you navigate the storied isles of the Aegean, take in charming sites including the castle-town of Monemvasia, stroll secluded lanes of Paros and car-free Hydra, with their white-washed houses with doors graced by pink bougainvillea, and admire the dramatic coastline (more than 70 beaches!) of mountainous Milos. 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. The First Officer will provide deeper insights into the fascinating world of a tall ship.

Day 3
Nauplio / Peloponnese

The old town of Nafplion has a picturesque peninsula setting and three Venetian fortresses guard the pretty town. In ancient times, the excavation site of Mycenae, a UNESCO World Heritage Site, was one of the most important towns in Greece. Its legendary king, Agamemnon, has a large role in Homer's Iliad. The palace grounds were surrounded by a cyclopean stone wall. Now you can only gain entrance through the famous Lion Gate. In Epidaurus, also protected by UNESCO, the impressive 14,000-seat theater is one of the most important buildings in this archaeological site.

Day 4
Monemvasia / Peloponnese

The little town of Monemvasia nestles closely against a rock that lies just off the coast. This impregnable fortress was an important trading center in Byzantine times. Today it is a retreat for wealthy Athenians who spend their weekends here. Behind its walls you can discover the beautifully restored lower town, where you simply want to drift along the tranquil narrow lanes. This picturesque little town on a rock transports you back in time to the romantic Middle Ages, when it was exceptionally modern and lively.

Day 5
Milos / Cyclades

The unique character of Milos' landscape was formed by volcanic activity. Hot springs, spectacular cliffs and distinctive rock formations give the various beaches their own individual character. The colors of Milos are most obvious where the water meets the stone and forms the coastline. Minerals have colored the sand and stones and each rock along the coastline seems to glow in a different color. Plaka, the picturesque old capital with its typical dazzling-white houses, is overlooked by a mighty castle that offers a superb view over Adamos Bay and the surrounding islands.

Day 6
Paros / Cyclades

Whitewashed facades, blue windows, and doors that sparkle with the pink blossoms of the bougainvillea—with its Aegean postcard idyll, Paros is reminiscent of its famous Cycladic sister, Mykonos, at first glance. A second glance, however, quickly reveals the differences: no crowds, no over-the-top party scene. Paros relies on gentle tourism and has therefore been able to retain much of its original charm. Besides the pretty main towns of Parikia and Naoussa and the fabulous island beaches, the wild hinterland with its traditional villages and monasteries is also worth a trip.

Day 7
Hydra / Saronic Islands

In Hydra's small northern capital that shares the same name as the island, houses crowd the slope up to the castle ruins above the harbor entrance like a cubist painting. The whole town is listed as a historic monument and there are no cars, only fishing boats and donkey carts. This “bare rock in the sea” (almost all trees were chopped down and used to build ships) once produced proud sailors and admirals. The thunder of the canons had long ceased when Sophia Loren came to the island and made it famous with the film Boy on a Dolphin. Canadian singer Leonard Cohen was also one of many artists who lived on Hydra during the sixties. Nowadays, wealthy Athenians come to relax on the island, which lies just 40 miles from the capital in the Saronic Gulf, and where property prices are the highest in Greece and luxury yachts roll gently in the harbor.

Day 8
Piraeus / Athens

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



Discover the Peloponnese Peninsula and lesser-known Cyclades islands and their secrets, far from the tourist crowds
Visit the World Heritage Site of Mycenae, one of the most important archaeological sites in Greece
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, Cultural Adventures, Walking, Small Ship Cruising
Trip Level:

7-day cruise, cultural explorations and walking tours