Sprinkled across the Aegean Sea and steeped in ancient mythology, the Cyclades are some of the most spectacular of Greece's many isles. Here, fishing boats cast colorful reflections in azure waters, whitewashed villages cascade down lavender-dusted slopes, and craggy headlands are punctuated by ancient ruins. Under the billowing sails of the exquisite four-masted tall ship Sea Cloud, voyage to rugged Sífnos, sun-drenched Santorini, the mystical isles of Delos, and more.

This trip is offered in partnership with Lindblad Expeditions.


Days 1-2: U.S./Athens, Greece/Piraeus

Arrive in Athens after an overnight flight and visit the Acropolis Museum; then travel to Piraeus, where we will board the majestic Sea Cloud. Cast off this afternoon, and take in our first Grecian sunset at sea.

Meals Included:Lunch, Dinner Daily
Accommodations:Sea Cloud
Day 3: At Sea

Enjoy a glorious day of sailing among the evocative isles of the Cyclades. Relax on deck with a book, observe the crew as they man the rigging and trim the sails, and attend presentations by our team of experts on the area’s history and ecology. In the late afternoon, we may have a chance for an impromptu swim.

Meals Included:Breakfast, Lunch, Dinner
Day 4: Tinos

Drop anchor at beautiful Tinos, dotted with villages steeped in Venetian history. The island’s Venetian-era dovecotes, terraced hillsides, and green marble quarries have long made this a haven for artists. Explore the picturesque village of Pyrgos, adorned with carved marble facades, and visit the church of Panagia Evangelistria, where thousands of pilgrims come every year to pray at one of Greece’s holiest shrine.

Meals Included:Breakfast, Lunch, Dinner
Day 5: Delos

The tiny archaeological gem of Delos is the birthplace of the twin gods Artemis, goddess of animals and the hunt; and Apollo, god of healing, music, and light. Spend the morning discovering the island’s incredible ruins, including the Terrace of the Lions and the exquisite Temple of Apollo. In the afternoon, we'll sail among the surrounding islands and choose a promising one to explore.

Meals Included:Breakfast, Lunch, Dinner
Day 6: Amorgós

Drop anchor at Amorgós, the easternmost isle of the Cyclades. Visit the main city, perched in the mountains, and see its beautiful domed churches and windmills. Explore the dazzling white monastery of Panagia Hozoviotissa, clinging to a cliff face above the sea. Later, return to the Sea Cloud and enjoy a relaxing afternoon beneath its splendid sails.

Meals Included:Breakfast, Lunch, Dinner
Day 7: SantorIni

Incomparable Santorini is an island archipelago formed from a single volcanic cone that erupted in the second millennium B.C., burying the island's Minoan culture in ash. Sail into the caldera, and drive through windswept vineyards to the beautiful town of Oia. Set high on a cliff, Oia affords unrivaled views of the caldera below. Explore the ruins of the ancient city of Akrotiri, destroyed by a volcanic eruption thousands of years ago. After lunch, ride a cable car down the cliff side back to the ship.

Meals Included:Breakfast, Lunch, Dinner
Day 8: SÍfnos/At Sea

Drop anchor at Sífnos, a rugged island featuring a harbor lined with waterfront tavernas and a beautiful upper chora (village). This afternoon, find a spot on deck to watch the crew hoist the Sea Cloud’s sails by hand as we return to Piraeus.

Meals Included:Breakfast, Lunch, Dinner
Day 9: Piraeus/Athens/U.S.

Disembark this morning and transfer to the airport for your return flight.

Meals Included:Breakfast

Optional Extensions

Optional Extensions

  • Crete Extension
    3 days from $2,400
  • Athens Extension
    2 days from $1,460
Crete Extension


Explore the palace of a fabled king and the birthplace of a god on this adventure to the sun-drenched island of Crete. Learn about the intriguing civilization of the Minoans and their mighty fortresses with our knowledgeable guides, and get a taste of local traditions at a renowned winery and an artisans’ collective. Stroll along the shores of the azure Aegean, descend into a sacred cave where Zeus was said to have been born, and witness ancient ruins come to life.

Day 1: Athens, Greece/Crete

Disembark in the ancient port of Piraeus, then transfer to the airport in Athens for the flight to Heraklion, capital city of the Greek island of Crete. Check in to our hotel, situated near the turquoise harbor and the city center. Enjoy delicious Greek food for lunch, and then delve into the history of the island and its mythical kings during an informative talk. Crete’s early Minoan civilization take its name from the legendary King Minos, said to have had an elaborate labyrinth built which contained the monstrous Minotaur.

Meals Included:Lunch, Dinner
Accommodations:Aquila Atlantis Hotel
Day 2: Crete

Today, investigate Crete’s mythological mysteries while exploring the ruins and imaginatively reconstructed Palace of Knossos, the ceremonial and political center of the Minoan civilization. Marvel at towering colonnades and colorful murals modeled after archaeologist Sir Arthur Evans’ interpretations of ancient decorative accents. Next, visit a state-of-the-art winery located in the Archanes region, where Crete’s oldest wine press—which dates to around 1550 B.C.—was found. Tour this privately-owned organic winery, and sample a variety of Greek and international varietals for a taste of an ancient tradition.

Meals Included:Breakfast, Lunch, Dinner
Accommodations:Aquila Atlantis Hotel
Day 3: Crete

Journey east to the high Lassithi Plateau, a vast patchwork of fertile fields bounded by the soaring Dikte mountains. In the village of Psychro, visit the famed Dikteon Cave, believed by some to be the birthplace of Zeus, ruler of the Olympian gods and father of Minos. Alters, clay figurines, shells, and other artifacts discovered within the cave suggest it has been a site of cult worship since at least Neolithic times. Later, at the Lassinthos Eco Park, meet local artisans and observe traditional workshops dedicated to pottery, woodworking, weaving, and more. Savor the flavors of fresh Cretan cuisine for lunch before heading back to Heraklion to explore on your own this evening.

Meals Included:Breakfast, Lunch
Day 4: Crete/Athens/U.S.

After breakfast, transfer to the airport in Heraklion and fly to Athens, then connect with your flight home.

Meals Included:Breakfast