Star Collector: Greek Classics & Hidden Gems Unveiled

From $8,299 per person

14 days

Ship: Wind Spirit

Star Collector: Greek Classics & Hidden Gems Unveiled
Windstar Cruises

 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.

Journey Summary

  • Day 1 - Jun. 4, 2026, Thu. - Athens, Greece
  • Day 2 - Jun. 5, 2026, Fri. - Ermoupoli
  • Day 3 - Jun. 6, 2026, Sat. - Kusadasi
  • Day 4 - Jun. 7, 2026, Sun. - Pythagoreio, Greece
  • Day 5 - Jun. 8, 2026, Mon. - Naxos, Greece
  • Day 6 - Jun. 9, 2026, Tue. - Folegandros, Greece
  • Day 7 - Jun. 10, 2026, Wed. - Milos, Greece
  • Day 8 - Jun. 11, 2026, Thu. - Athens, Greece
  • Day 9 - Jun. 12, 2026, Fri. - Nafplio
  • Day 10 - Jun. 13, 2026, Sat. - Mykonos
  • Day 11 - Jun. 14, 2026, Sun. - Kusadasi
  • Day 12 - Jun. 15, 2026, Mon. - Patmos
  • Day 13 - Jun. 16, 2026, Tue. - Santorini
  • Day 14 - Jun. 17, 2026, Wed. - Monemvasia
  • Day 15 - Jun. 18, 2026, Thu. - Athens, Greece

Itinerary Highlights

Ermoupoli, Greece, is a beautiful town is known for its neoclassical architecture, colorful buildings, and narrow streets. It has a strong Venetian influence, which differentiates it from the other Cycladic islands in the region.<br />
&nbsp;

Book this cruise

Detailed Itinerary

Day-by-day description of your cruise and cruise activities.

Day 1 - June 04, 2026

Athens, Greece

Athens is a treasure trove of history, with over 3,000 years of remarkable stories to tell. The awe-inspiring Acropolis, a UNESCO World Heritage Site, is a must-see. Stroll along the cobbled streets of the Plaka, lose yourself in its charm, and don't miss the impressive Acropolis Museum. For a special moment, make time to climb Pnyx Hill, where the sunset casts a golden glow on the Parthenon, creating picture-perfect memories. Discover local details by picking up a set of Greek komboloi—or worry beads—as a keepsake. Even the city's metro stations have surprises, doubling as mini-museums showcasing fascinating artifacts unearthed during construction. Athens seamlessly blends ancient wonders with modern vibrancy, making it an unforgettable destination.

Day 2 - June 05, 2026

Ermoupoli

Step into the timeless charm of Ermoupoli, Syros’s stunning capital. This hidden gem is sprinkled with vibrant, pastel-colored houses that seem to cascade down its hills. Wander through its enchanting narrow streets, where stone stairways and medieval arches form a maze you can’t help but explore. At the hilltop, you’ll find the majestic Aghios Georgios Cathedral, along with the serene Capuchin and Jesuit monasteries. Don’t miss the heart of the town, the old Piatsa square, a picture-perfect spot that feels plucked from another era.

Day 3 - June 06, 2026

Kusadasi

Experience a blend of rich history and natural beauty at Ephesus, known as one of the most iconic outdoor museums in the world. Wander through ancient landmarks that whisper stories of a bygone era. A visit to Bulbul Mountain reveals a remarkable sight—homes where one roof seamlessly becomes the terrace of another. As the sun sets, delight in a magical evening with our exclusive Destination Discovery Event. Savor a moonlit dinner paired with a memorable concert, staged either along the timeless Harbor Street or near the grand Celsus Library in Ephesus.

Day 4 - June 07, 2026

Pythagoreio, Greece

Welcome to Pythagoreio, the crown jewel of Samos Island, Greece. Nestled along a stunning coastline, this vibrant town offers an enchanting blend of history, culture, and natural beauty. Its charming harbor, brimming with colorful fishing boats and sleek yachts, invites leisurely waterfront strolls. Relish fresh seafood at family-run tavernas or sip a coffee while watching the world go by. Venture further to uncover ancient treasures like the Temple of Hera, or simply soak in the serene atmosphere that makes Pythagoreio a haven for relaxation-seekers. A destination where timeless charm meets modern comforts, Pythagoreio promises an unforgettable escape.

Day 5 - June 08, 2026

Naxos, Greece

Naxos, the largest gem of the Cyclades, is a vibrant island of history and Greek charm. Crowned by Mount Zas, it offers lush landscapes, quaint villages like Apiranthos, and sparkling beaches such as Agios Prokopios and Plaka. The town of Chora enchants with its timeless Venetian architecture, weaving alleys, and the famous Portara—an ancient gateway standing proud on the horizon. Naxos is also a feast for the senses, with fresh produce like cheese, potatoes, and citrus transforming every meal into a taste of tradition.

Day 6 - June 09, 2026

Folegandros, Greece

Discover the serene beauty of Folegandros, a hidden treasure in the Cyclades that promises a truly authentic Greek island experience. Perched dramatically above the Aegean, this small-ship-exclusive destination impresses with rugged cliffs and breathtaking vistas. Wander through Chora, a quaint and picturesque village filled with whitewashed homes, narrow passageways, and centuries-old Venetian charm. Step back in time at Ano Meria, where traditional island life carries on undisturbed by modernity. Relax on the island’s pristine beaches, such as Agali and secluded Katergo, where turquoise waters are perfect for a refreshing swim. With its serene ambiance and understated allure, Folegandros is a haven for travelers seeking peace, authenticity, and natural beauty.

Day 7 - June 10, 2026

Milos, Greece

Nestled in the shimmering Aegean Sea, Milos is a destination brimming with beauty and charm. Famous for its vibrant volcanic landscapes, this "Island of Colors" is adorned with extraordinary beaches like Sarakiniko, where powdery white rock formations meet serene turquoise waters. Here, you can swim, sunbathe, and marvel at nature’s artistry. History enthusiasts will find Milos captivating, with its ancient catacombs and the very site where the famous Venus de Milo statue was unearthed. Wander through Plaka, the island’s enchanting hilltop capital, offering panoramic views and a timeless atmosphere. Don’t forget to savor the island's local specialties, like pitarakia, delicious little cheese pies packed with rich flavor.

Day 8 - June 11, 2026

Athens, Greece

Step back in time as you explore Athens, a city with over 3,000 years of history waiting to be uncovered. Be sure to visit the iconic Acropolis, a UNESCO World Heritage site, and stroll through the charming Plaka neighborhood with its vibrant shops and cafés. The Acropolis Museum is another must-see, offering fascinating exhibits that showcase the city’s ancient past. For a truly unforgettable experience, climb Pnyx Hill to capture stunning views of the Parthenon, especially at sunset. Don’t forget to pick up a set of traditional Greek worry beads, known as komboloi, as a keepsake. And, to add an unexpected twist to your day, check out the city’s metro stations, which double as mini-museums featuring recently unearthed relics.

Day 9 - June 12, 2026

Nafplio

Nafplio, a seaside gem on the Peloponnesian coast, exudes romance at every turn. Wander through its age-old cobblestone streets lined with blooming bougainvillea and stately neoclassical homes. Take a leisurely stroll in Syntagma Square, where history and charm come together beautifully. Feel adventurous? Climb the 999 stone steps of Palamidi Castle, carved right out of the rock, and be rewarded with breathtaking views. Dive deeper into history with optional guided tours to the ancient UNESCO heritage sites of Epidaurus and Mycenae—famed for its iconic Lion’s Gate. Whether you're seeking history, beauty, or just a serene walk, Nafplio promises an unforgettable experience.

Day 10 - June 13, 2026

Mykonos

Picture waking up to the enchanting, whitewashed beauty of Mykonos. This classic Greek island is dotted with charming churches and iconic thatched windmills, nestled in a vibrant harbor filled with fishing boats and luxurious yachts. For a deeper dive into history, consider an optional excursion to Delos. A short ferry ride brings you to this UNESCO World Heritage Site, where legends say Apollo was born. Explore ancient ruins that date back to the 6th century B.C., and let the mythical charm of the Aegean transport you to another time.

Day 11 - June 14, 2026

Kusadasi

Explore the mesmerizing charm of Ephesus, one of the world's greatest open-air museums where history comes alive at every step. Stroll through legendary landmarks rich with tales of the past. Then, ascend to the terrace houses on Bulbul Mountain, marveling at the ingenious layout where the roof of one house becomes the terrace for the next. As the sun sets, immerse yourself in a magical evening. Enjoy a moonlit dinner and exclusive concert in the shadow of the majestic Celsus Library or along the ancient Harbour Street. This is cultural immersion at its finest.

Day 12 - June 15, 2026

Patmos

Patmos is a destination steeped in both history and beauty. This sacred island, revered as the place where St. John penned the Book of Revelation, offers a peaceful retreat with dramatic landscapes and volcanic cliffs. Explore the famed Cave of the Apocalypse, where history seems tangible, or visit the stunning Holy Monastery for a glimpse into centuries-old traditions. Nature enthusiasts will adore the island’s rugged coastline and serene charm.

Day 13 - June 16, 2026

Santorini

Imagine gliding toward Santorini, with its striking cliffs embracing the endless blue sea—a sight that feels almost otherworldly. Step ashore and explore the enchanting village of Oia, famous for its charming whitewashed buildings and iconic blue domes. Dive into history with a visit to the Bronze Age ruins of Akrotiri, a fascinating UNESCO treasure. As the sun sets, savor a glass of chilled local Assyrtiko wine—a bright and crisp reminder of the island’s natural gifts. This is the kind of magic only small ship travelers truly get to savor.

Day 14 - June 17, 2026

Monemvasia

This unique coastal town is connected to the mainland by a narrow causeway. Its history stretches back to the 12th century, with ancient town walls and charming churches to explore. In the upper town, step into the past as you visit a historic castle and the Agia Sophia, a mesmerizing Byzantine church. Stroll through the lower town, where quaint lanes are lined with beautifully restored Venetian mansions. Finally, unwind on the smooth pebble beach and soak up the Mediterranean sunshine.

Day 15 - June 18, 2026

Athens, Greece

Step into the heart of ancient history in Athens, where every corner reveals a story. Discover the legendary Acropolis, a marvel of human achievement and UNESCO World Heritage site. Stroll through the lively Plaka neighborhood, a charming area filled with quaint shops, inviting cafés, and winding streets that feel untouched by time. Make your way to the Acropolis Museum, home to an extraordinary collection of artifacts that bring Athens’ illustrious past closer than ever. For a magical moment, head to Pnyx Hill at sunset to capture breathtaking views of the Parthenon bathed in golden light. Don’t forget to pick up a set of traditional Greek komboloi (worry beads) or explore the city’s metro stations, where ancient relics are elegantly displayed, creating museums beneath your feet. Every step in Athens is a step through time—don’t rush the journey.

Dates and Prices

Select year & month:

Unavailable dates are greyed out

JanFebMarAprMayJunJulAugSepOctNovDec

Available dates:

Jun 04, 2026

consultation

Need information to make a decision?

Reach out to our travel concierges today to create your perfect journey.