Undiscovered Greek Islands

Uncommon Encounters in the Aegean Sea aboard the Callisto


Skyros, Chios, Sifnos and Amorgos are among the jewels of the Aegean Sea and yet remain relatively unknown to most travelers. These undiscovered islands represent a wonderful cross-section of history, culture, and architectural styles. On Skyos, God-like Achilles hid to avoid joining the Trojan War, and King Philip II, father of Alexander the Great, met and fell in love with his wife, Olympias. Chios is the reputed birthplace of Homer, Sifnos was famed for its wealth because of its gold and silver mines, and Amorgos was an important center of Cycladic culture.

On this voyage aboard the 34-guest Callisto, you’ll make your own discoveries of these enchanting isles, with their pristine shorelines, magnificent landscapes, important monuments, and villages unchanged for centuries. After exploring Athens, you’ll sail the Aegean Sea, encountering charming villages, legend-filled shores, and historic sites including Amorgos’s 1,000-year-old monastery of Panaghia Chozoviotissa, which hangs some 800 feet above the sea on a vertical cliff face. And early fall in Greece is an ideal time to cruise the Aegean Sea—the light is golden and the days pleasantly warm.

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, Sep 24, 2022
Athens, Greece

Arrive in Athens and transfer to the elegant Hotel King George (or similar), conveniently located on Syntagma (Constitution) Square, the center of the city. Enjoy dinner at a local restaurant.

Day 2, Sep 25, 2022
Athens / Schinias National Park / Marathon

Accompanied by local naturalists, drive in the morning to Schinias National Park, a protected ecosystem complex that consists of a wetland and a coastal pine forest that is home to about 270 recorded bird species, including many migrants, and a rich flora. The visit to this important reserve will give you a good introduction to the natural world of Greece. Nearby, tour Marathon, the site of the great battle fought in 490 BC between the large invading army of the Persian Empire and the much smaller force of mostly Athenian citizen-soldiers that resulted in the victory of the Athenians. A runner was sent to Athens, 26 miles away, to announce the victory, initiating the race known today as the “marathon.” Enjoy lunch at a country taverna. On the return to Athens, stop at the Vorres Museum, which houses the collection of Ion Vorres in his beautiful villa and gardens, and an adjoining hall. Dinner on your own and overnight at hotel.

Day 3, Sep 26, 2022
Explore Athens / Embark

One of the world’s most venerable cities, Athens is the capital of Greece and Europe’s oldest city. Its ancient monuments are testimonials to a glorious past that gave birth to democracy and witnessed the origins of many ideas, arts, and sciences that constitute the Western tradition. Explore the Agora, the civic and commercial center of ancient Athens and the living heart of its democracy and the Agora Museum. After lunch at a local restaurant, visit the Acropolis and its celebrated monuments, including the Parthenon, and the Acropolis Museum, which houses an outstanding collection of sculptures and other artifacts. Continue to the coast and board the Callisto and set sail.

Day 4, Sep 27, 2022

Famed in antiquity for its wealth produced by its gold and silver mines, Sifnos is one of the most delightful of the group of islands in the center of the Aegean Sea known as the Cyclades. Here, the distinctive whitewashed cubic style of architecture prevails. Visit the former island capital of Kastro, an impeccably kept village that has retained much of its medieval character; Apollonia, a labyrinth of white houses, flowers, and belfries; and its twin village Artemonas, with its impressive Venetian-style mansions. You will also explore the island’s beautiful landscape and look for birdwatching opportunities.

Day 5, Sep 28, 2022

Few islands combine so much history and such dramatic scenery as Amorgos. First settled in the 5th millennium BC, it was in the 3rd millennium BC that marked Amorgos’ initial apogee when it became an important center of Cycladic culture that produced the distinctive figurines that are found in many of the world’s major museums. After arriving at the island’s harbor town, tour the remains of ancient Minoa, which was founded in the 10th century BC, and attained its prominence from the 4th century BC to the Roman period. Continue to the famed Monastery of Chozoviotissa, one of the most unforgettable sights in the Aegean. Dating to the 11th century, the monastery is sited in a spectacular setting, clinging a sheer cliff above the sea. We will also explore the main town of Amorgos, clustered around a hill crowned by a fortress, as well as the northern part of the island, which reveals the rugged beauty of the island, including the attractive harbor town of Aigiali, ringed by majestic mountains, and the hill village of Langada, where, in a nearby gorge, you may see the elusive Ruppell’s warbler and other bird species.

Day 6, Sep 29, 2022

Awake this morning in Chios, the island that claims Homer as a native son. Since ancient times, Chios prospered through trade, becoming a center of learning and the arts. In the morning, drive to the Monastery of Nea Moni, built in the 11th century in a wooded vale. Now a UNESCO World Heritage site, Nea Moni is decorated with exquisite luminous mosaics and frescoes. In the main town of Chios, visit the Archaeological Museum, whose collection illustrates the richness and individuality of the island. In the afternoon, explore the old mastic villages in the south of the island, including Pyrgi, where the house-fronts are decorated in gray and white geometric designs. Chios is an excellent place to observe birds, and you can take a birdwatching excursion.

Day 7, Sep 30, 2022

An island of great natural beauty, remote Samothraki’s central massif rises to the great peak of Mount Fengari. According to Homer’s Iliad, it was from this peak that Poseidon, god of the sea, watched the fighting during the Trojan War. Visit the Sanctuary of the Great Gods, one of the most important ancient sites in Greece, a place of worship where mysteries were held. The secret rites performed here attracted famous pilgrims, included Philip II, the father of Alexander the Great, who met and fell in love with his wife and mother of Alexander, Olympias. The statue of the Winged Victory of Samothrace, now in the Louvre, was discovered here in 1863, and subsequent archaeological excavations have revealed the extensive remains of the site. Nature lovers and birdwatchers will be rewarded on their exploration of Samothraki’s lush forested and waterfalls that plunge into deep pools.

Day 8, Oct 1, 2022
Alexandroupolis / Evros River Delta / Dadia National Park / Xanthi

From the port town of Alexandroupolis, on the northeastern Greek mainland, you have a choice of two excursions: The Evros River Delta and Dadia National Park, or the attractive old town of Xanthi. One of the most important bird habitats in Europe and a Ramsar Wetland of International Importance, the Evros River Delta is home to more than 300 species of birds as well as over 350 plant species. After exploring this riverine world and observing its birds, continue to Dadia National Park, a vast protected deciduous forest that is an important stop for migrating birds. But it’s the raptors that are the main attraction of Dadia. Of the 38 species of Europe’s birds of prey, 36 are resident here. Alternatively, take an excursion to Xanthi, a prosperous market and university town, whose old section is filled with beautiful 19th century mansions, and its narrow streets are lined with shops and cafes.

Day 9, Oct 2, 2022

According to the legend, Achilles, the “god-like” hero of the Iliad, hid on Skyros to avoid joining the Trojan War. He did not succeed, and as the legend also has it, he rode a Skyrian horse into Troy. Now a protected endangered species, the small-bodied Skyrian horses can still be seen in the wild on the island. With its small bays, rolling farmland and pine forests, Skyros is an appealing island. Explore tranquil Skyros Town, which is perched on a high rock, topped by a Venetian fortress dating from the 13th century. Wander through its attractive winding cobblestone alleyways, and visit the superb Folk Museum, housed in a 19th century mansion, whose collection tells the mythology and folklore of the island. You will also visit the Byzantine Monastery of St. George, founded in 962, to admire its ornate gilded screen. Skyros has been known through the centuries for its local artists—potters, painters, weavers, and sculptors. You will visit the workshop of some of them who carry the tradition to this day. At this time of the year, the island attracts birders who come in search of Eleonora’s falcon, which migrates annually between here and far away Madagascar.

Day 10, Oct 3, 2022
Piraeus / Depart

Arrive in Piraeus, disembark, and transfer to Athens’s airport for homeward-bound flight.



Cruise the Aegean Sea and explore some if its uncrowded and unspoiled isles
Visit charming villages, legend-filled shores, and historic sites, including Amorgos’s 1,000-year-old monastery of Panaghia Chozoviotissa
Sifnos, with its classic Cycladic style of architecture; Amorgos, an island of golden beaches and crystal-clear waters.
The superb mosaics and frescoes of 11th century Nea Moni monastery on Chios, the rugged islands of Samothraki and Skyros


Length: 10 days
Cost From: $6990  
Arrive: Athens, Greece
Depart: Athens, Greece
Lodging: 7 nights aboard a 34-passenger vessel, 2 nights hotel
Meals: All meals aboard ship, including wine, beer, and soft drinks with lunch and dinner
Activity: Archaeology, Cultural Adventures, Walking, Special Interest, Small Ship Cruising
Trip Level:

7-day cruise, cultural explorations, swimming, and walking tours