Sailing the Greek Isles

Arrive in Athens and head straight to the port of Piraeus to board your ship in the late afternoon. Get settled in your cabin, then step onto the deck, grab a glass of champagne, and soak in the excitement as you set sail into the evening.

Spend your first morning at sea, sailing toward the Cyclades on a classic tall ship. Relax on deck, take in the stunning Aegean views, and watch the crew trim the sails by hand. Join expert-led discussions to learn about the region’s history and ecology as your adventure begins.

Drop anchor at the island of Tinos, a sculptor’s haven dotted with villages full of terraced hillsides, Venetian-era dovecotes, and quarries renowned for their superb green marble. Explore the picturesque village of Pyrgos, generously adorned with carved marble facades. And visit the Church of Panagia Evangelistria. Built around a miraculous icon, it’s Greece’s holiest shrine–and thousands of pilgrims make their way here every year to pray.

The easternmost island of the Cyclades, Amorgós is a bit less frequented than many, but no less impressive. After dropping anchor, take in the beautiful domed churches and windmills of the main city, a scenic enclave perched in the mountains. Explore the Panagia Hozoviótissa monastery, clinging tenaciously to a cliff face above the sea. Like so many others in this region, it was built a millennium ago to protect a precious religious relic.

Venture into remarkable Santoríni—an island archipelago formed from a single volcanic cone that erupted 3,600 years ago to bury the resident Minoan culture in ash. Sail directly into the caldera and then drive through windswept vineyards to reach spectacular high views from the town of Oía. Tour the Archaeology Museum and excavations at Akrotiri, an important Minoan town preserved under volcanic ash like Pompeii, with well-built houses, streets, waterworks, pottery and art.

Designated a UNESCO World Heritage Site in its entirety, uninhabited Delos is an outstanding archaeological gem. In myth, it’s the birthplace of the twin Greek immortals Artemis (goddess of animals and the hunt) and Apollo (god of healing, music and light). Spend a morning surveying the Terrace of the Lions and exquisite Temple of Apollo, among the many incredible ruins preserved here. This afternoon, the adventure continues aboard the ship.

In the morning, set foot on a rugged island known for its flavors, its beaches, its 227 churches and its poets. A quaint harbor and scenic upper chora (village) invite exploration, and tempting local comestibles can be found at a waterfront taverna. This is also a fine place for a brisk walk or a lazy stroll along the beach. As afternoon arrives, the crew prepares to hoist the sails once more and depart for Piraeus.

Disembark in Piraeus and transfer to the airport for flights home or explore more.