Sailing the Greek Isles

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 Sifnos, sun-drenched Santoríni, the mystical isles of Delos and Naxos, and more.

Days 1 & 2 — U.S./Athens, Greece/Piraeus

Depart on an overnight flight to Athens. After some time at leisure and lunch in the city, travel to Piraeus and settle into your cabin on the majestic Sea Cloud. Cast off this afternoon, and take in our first Grecian sunset at sea.
Sea Cloud (L,D)

Day 3 — At Sea/Sifnos

Our first morning on board is spent at sea. We may stop for a late morning swim before visiting the island of Sifnos. Distinguished for its pottery and its Venetian dovecotes, Sifnos is a rugged island with a harbor village and a beautiful upper chora (village), waterfront tavernas and convenient beaches. It’s a great island for walkers or loungers alike. This afternoon, find a spot on deck to watch as the Sea Cloud’s sails are hoisted up their impressive masts by hand as we set sail for the Cyclades.
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Day 4 — Tenos

Drop anchor at beautiful Tenos, 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 Greece’s holiest shrine.
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Day 5 — Delos/Naxos

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. Then sail to the fertile island of Naxos, where Cycladic civilization blossomed 5,000 years ago. Explore Naxos Town and its medieval Venetian castle, the seat of power from which the Venetians controlled the Cyclades for centuries.
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Day 6 — Amorgos

Drop anchor at Amorgos, 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.
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Day 7 — Santoríni

Incomparable Santoríni 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. After lunch, ride a donkey or a cable car down the cliff side back to the ship.
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Day 8 — 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 stop and a swim.
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Day 9 — Piraeus/Athens/U.S.

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