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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: 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 3: 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 4: 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 5: 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 6: 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 7: 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 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. 
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Thu Jun 18
Athens, Greece
Arrive:  
Depart:  5:00 PM
Watersports Platform: 
Fri Jun 19
Ermoupoli
Arrive:  7:00 AM
Depart:  4:00 PM
Watersports Platform: 
Sat Jun 20
Kusadasi
Arrive:  8:00 AM
Depart:  11:59 PM
Watersports Platform: 
Sun Jun 21
Pythagoreio, Greece
Arrive:  7:00 AM
Depart:  5:00 PM
Watersports Platform: 
Mon Jun 22
Naxos, Greece
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Tue Jun 23
Folegandros, Greece
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Wed Jun 24
Milos, Greece
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Thu Jun 25
Athens, Greece
Arrive:  7:00 AM
Depart:  
Watersports Platform: 
Wind Spirit
The Wind Spirit is a sleek, 4-masted sailing yacht accommodating 148 guests. With four decks and a gross tonnage of 5,736, Wind Spirit feels like your own private yacht.
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Accommodations & Pricing
Boutique cruising with fewer than 350 guests. Our expertly designed itineraries and unexpected shore excursions bring you closer to each destination.
The Windstar Life
The Windstar staff-to-guest ratio is 1:1.5, and it shows.The moment you board you’ll feel it: an ever-attentive crew at your service, providing you with what you want and need, when you want and need it.
Friendly and Relaxed Atmosphere
Signature Onboard Barbecue
Cooking Demonstrations
Genuine and Thoughtful Crew
Crew Talent Show
Open Bridge
Local and Live Performances
Relax at the Pool or Hot Tub
Complimentary 24 Hour Room Service
Signature Sail Away
Shopping With The Chef
Take In The Sun
Marina
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session