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Athens, Greece to Athens, Greece

Explore breathtaking, white-washed towns perched high on dramatic cliffs overlooking the azure Aegean Sea, discover sun-drenched hidden beaches with crystal-clear waters, and engage with local fishermen and charismatic villagers in charming small ports where larger ships can’t go. Roam the romantic mainland town of Nafplio and take in views from the hilltop Castle of Palamidi, one of the best-preserved castles in Greece. Visit the Grotto of St. John and witness nuns making honey and fruit liquor on the islet of Patmos. On the legendary island of Santorini, sip coffee while admiring the dramatic village of Oia. Wind around the narrow streets of secluded Monemvasia—a pedestrian-only village built into a cliffside. On the isle of Syros, visit the Venetian-influenced capital of Ermoupoli with neoclassical architecture and lively activity in Miaouli Square. An important center of Hellenic culture, Samos boasts the famous Heraion UNESCO site where the goddess Hera was born according to Greek mythology. A late night in Naxos allows the luxury of time to explore and relax. Spend the day at some of the most beautiful beaches in the Cyclades or hike Mount Zas for breathtaking panoramic views. The delight of one late night in port leads to another the following day at Folegandros, one of the Cyclades’ most picturesque islands. Its wild natural landscape and unspoiled charm are a photographer’s dream. And for something 180 degrees from ordinary, embark on the lunar-like landscape of Milos. This voyage blends traditional ancient sites with an intriguing hidden side of Greece most travelers have never seen and won’t soon forget.

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Day 1: Athens, Greece

With 3,000 years of history, you can’t turn around in Athens without encountering the past. The Acropolis, a UNESCO site, the Plaka, and the Acropolis Museum are must-sees. But leave time if you can to climb Pnyx Hill for photos of the Parthenon at sunset, to buy your own set of Greek komboloi (worry beads), and to explore the metro stations that serve as mini-museums for the relics that are constantly being unearthed.

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Day 2: Nafplio

This charming seaside town on the Peloponnese is one of the most romantic cities in Greece. Enjoy the medieval old town with narrow cobblestone alleys, and neoclassical mansions with bougainvillea trees adorning the balconies. Take an optional tour to the UNESCO site of Epidaurus or the UNESCO site of Mycenea, ancient ruins including the famous Lion’s Gate. Stroll the Syntagma Square and take in the beauty of the Palamidi Castle with its 999 steps carved from the rocks. The view is breathtaking.

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Day 3: Mykonos

Wake this morning to the postcard-like scene of Mykonos, the classic Greek isle dotted with hundreds of whitewashed churches and thatch-roofed windmills, in a harbor bobbing with fishing boats and luxurious private yachts. An optional tour including a scenic ferry ride takes you back to the 6th century B.C. to the tiny island of Delos, a UNESCO site and the mythical birthplace of Apollo.

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Day 4: Kusadasi

Few places offer such a rich combination of history and scenic beauty. In Ephesus, one of the greatest outdoor museums in the world, you’ll explore legendary sites steeped in history. Also visit the houses of Bulbul Mountain, where the roof of one forms the terrace of the next. This evening we present our Destination Discovery Event -- dinner in the moonlight and a concert near the Celsus Library or on Harbour Street in ancient Ephesus.

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Day 5: Patmos

This UNESCO World Heritage Site is known worldwide as the sacred island where St. John wrote the Book of Revelation, Patmos is the ideal place for nature lovers with its coastline of sheer cliffs and its volcanic soil. Highlights of Patmos include the Cave of the Apocalypse and the Holy Monastery of the Apocalypse.

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Day 6: Santorini

As our yacht approaches the spectacular cliffs rising from the deep azure sea, you’ll understand the magic of this area, where some say the ruins of Atlantis remain hidden. Visit the village of Oia and see the iconic Santorini blue domes or take a guided tour of Bronze Age excavations at the UNESCO site of Akrotiri. Toast the day with a crisp, cold glass of local Assyrtiko wine and appreciate the magic accessible to small ships like ours.

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Day 7: Monemvasia

This Gibraltar-like town tied to the mainland by a single thread of causeway holds treasures that are old even by Mediterranean standards, with town walls and several churches dating to the 12th century. Climb to the upper town for an up-close look at the castle and Agia Sophia, a Byzantine church. Wander the lanes of the lower town lined with Venetian mansions, many of which have been lovingly restored. Savor the sun on a smooth pebble beach.

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Day 8: Athens, Greece

With 3,000 years of history, you can’t turn around in Athens without encountering the past. The Acropolis, a UNESCO site, the Plaka, and the Acropolis Museum are must-sees. But leave time if you can to climb Pnyx Hill for photos of the Parthenon at sunset, to buy your own set of Greek komboloi (worry beads), and to explore the metro stations that serve as mini-museums for the relics that are constantly being unearthed.

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Day 9: Ermoupoli

Ermoupoli, the capital of Syros, opens the door to a little-known Greek island packed with rainbow-colored houses clinging to the hillsides. Not much has changed here since medieval times and the narrow cobblestone streets full of stairways and arches create a delightful maze. Sites to see include the Aghios Georgios Cathedral at the top of the hill, the Capuchin and Jesuit monasteries, and the picturesque main square known as the Piatsa.

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Day 10: Kusadasi

Few places offer such a rich combination of history and scenic beauty. In Ephesus, one of the greatest outdoor museums in the world, you’ll explore legendary sites steeped in history. Also visit the houses of Bulbul Mountain, where the roof of one forms the terrace of the next. This evening we present our Destination Discovery Event -- dinner in the moonlight and a concert near the Celsus Library or on Harbour Street in ancient Ephesus.

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Day 11: Pythagoreio, Greece

Pythagoreio is a charming coastal town on the island of Samos, Greece, offering a picturesque harbor and a rich historical backdrop. Known for its association with the ancient Greek mathematician Pythagoras, the town's vibrant marina is lined with traditional fishing boats and modern yachts, creating a lively yet relaxed atmosphere. Visitors can stroll along the waterfront, enjoy seafood at local tavernas, or explore nearby ancient ruins, such as the Temple of Hera. The town's blend of ancient history, natural beauty, and welcoming locals makes it a perfect destination for travelers seeking culture and tranquility.

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Day 12: Naxos, Greece

Naxos, the largest island in the Cyclades, Greece, is celebrated for its rich history and vibrant culture. Dominated by Mount Zas, the island boasts lush valleys, charming villages like Apiranthos, and stunning beaches such as Agios Prokopios and Plaka. Naxos Town, or Chora, captivates visitors with its Venetian architecture, narrow alleys, and the iconic Portara (The Great Door), the ancient gateway to the Temple of Apollo. Renowned for its agricultural produce, Naxos offers delectable local cuisine featuring cheeses, potatoes, and citrus fruits.

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Day 13: Folegandros, Greece

Folegandros, a serene gem in the Cyclades, Greece, is a small ship exclusive port. It enchants with its untouched beauty and tranquil atmosphere. Known for its dramatic cliffs and stunning views of the Aegean Sea, the island features the charming main town of Chora, with whitewashed houses, narrow streets, and Venetian architecture. The picturesque village of Ano Meria offers a glimpse into traditional island life, while pristine beaches like Agali and Katergo provide perfect spots for relaxation and swimming. Folegandros’ peaceful ambiance makes it an ideal destination for those seeking a quiet, authentic Greek island experience.

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Day 14: Milos, Greece

Milos, Greece , is famed for its unique volcanic landscape and crystal-clear waters. Known as the "Island of Colors," Milos boasts stunning beaches like Sarakiniko, with its moon-like white rock formations and tranquil waters, this is a great spot to swim and sunbathe. The island's rich history is reflected in its ancient catacombs and the site where the Venus de Milo statue was discovered. Milos’ capital, Plaka, is picturesque and built on a hill looking over the Aegean Sea. Make sure you try the pitarakia (cheese pies), one of Milos’ specialties

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Day 15: Athens, Greece

With 3,000 years of history, you can’t turn around in Athens without encountering the past. The Acropolis, a UNESCO site, the Plaka, and the Acropolis Museum are must-sees. But leave time if you can to climb Pnyx Hill for photos of the Parthenon at sunset, to buy your own set of Greek komboloi (worry beads), and to explore the metro stations that serve as mini-museums for the relics that are constantly being unearthed.

A Complimentary Windstar Destination Discovery Event