Off The Beaten Path Greek Islands
 
Athens, Greece to Athens, Greece
Thu Jun 18, 2026 - Thu Jun 25, 2026,
 7 days
 on Wind Spirit
?All-inclusive from
$4,999
?Cruise Only From
$4,999
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Athens, Greece to Athens, Greece
Set a course for hidden harbors and the delights of off the beaten path Greece during a seven-day cruise to Hellenistic islands and a moonlight dinner concert in the Turkish ruins of Ephesus. Explore the colorful interior of the Cathedral of St. George atop Syros, a stately, hillside landmark founded in the 1200s and continually restored after devastating battles. Listen as a moonlight concert reverberates across the ancient Celsus Library walls during your candlelight dinner in Ephesus. Drink the decadent sweetness of local Muscat wines pressed at Samos and learn about their most famous and calculating resident--the mathematician Pythagora. Wander the weathered Doric decor of the Temple of Demeter prior to sampling the culinary perfection of pan-seared calamari in Naxos. Relax on the sunny and sandy expanses of the most scenic beaches in the Cyclades. Browse handmade clothing in unspoiled Folegandros and Milos--tiny island refuges yet to be found by tourists.
voyage map
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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
TBA
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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. 

A Complimentary Destination Discovery Event

Join us for a once-in-a-lifetime experience after hours during this Evening in Ephesus event exclusive to Windstar guests. Enjoy a 5-course, white-glove-service dinner under the stars accompanied by a trio from the Aegean Chamber Orchestra. Surround yourself in the magic of these ancient ruins, and delight in every detail.

Wind Star/Wind Spirit: This event takes place in the Ephesus Library.
Star Legend/Star Pride: This event takes place on Harbor Street.

Please note: This Destination Discovery Event has been scheduled in a way that will allow you to book and experience another shore excursion on the same day and you will not miss anything.
Popular Highlights
Apeiranthos Village
From Naxos, Greece, explore Apeiranthos Village, a traditional mountain village known for its well-preserved architecture, marble-paved streets, and scenic views
Ermoupoli
Ermoupoli  is a beautiful town 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.
 
Kusadasi
Late night stays in Kusadasi, Naxos, and Folegandros allow for plenty of time to explore before returning back to your ship.
Milos, Greece
Take a tour in Milos, Greece to see the lunar-like landscape, created by a volcanic eruption over 2 million years ago.
Panagia Church
Walk to the Panagia Church in Folegandros, Greece to get stunning view of the Aegean Sea.
Samos
On Samos, explore charming villages like Kokkari and Pythagoreio, each offering a blend of traditional architecture and bustling harbors.
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports 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.
Category B
Category B
Every inch of your stateroom is designed for comfort. Luxurious Egyptian cotton linens wrap you in pleasant sleepiness as you stretch out in your queen bed (can be separated into twins if you prefer). Your spacious bath features granite counter tops, ample storage, and a roomy shower with massage shower head. L’Occitane® bath products invite you to indulge, while comfy waffle-weave robe and slippers entice you to relax. You’ll find fresh fruit and flowers always waiting for you after a day of sun or sightseeing. And, of course, everything else you need and expect — flat-screen television and DVD, private safe. And always at your fingertips, anything you wish from room service.
? Cruise only from $4,999 per guest
? All-inclusive price from $4,999 per guest
Category BX Deluxe
Category BX Deluxe
Every inch of your stateroom is designed for comfort. Luxurious Egyptian cotton linens wrap you in pleasant sleepiness as you stretch out in your queen bed (can be separated into twins if you prefer). Your spacious bath features granite counter tops, ample storage, and a roomy shower with massage shower head. L’Occitane® bath products invite you to indulge, while comfy waffle-weave robe and slippers entice you to relax. You’ll find fresh fruit and flowers always waiting for you after a day of sun or sightseeing. And, of course, everything else you need and expect — flat-screen television and DVD, private safe. And always at your fingertips, anything you wish from room service.
? Cruise only from $5,299 per guest
? All-inclusive price from $5,299 per guest
Category A
Category A
Every inch of your stateroom is designed for comfort. Luxurious Egyptian cotton linens wrap you in pleasant sleepiness as you stretch out in your queen bed (can be separated into twins if you prefer). Your spacious bath features granite counter tops, ample storage, and a roomy shower with massage shower head. L’Occitane® bath products invite you to indulge, while comfy waffle-weave robe and slippers entice you to relax. You’ll find fresh fruit and flowers always waiting for you after a day of sun or sightseeing. And, of course, everything else you need and expect — flat-screen television and DVD, private safe. And always at your fingertips, anything you wish from room service.
? Cruise only from $5,699 per guest
? All-inclusive price from $5,699 per guest
Category AX Deluxe
Category AX Deluxe
Every inch of your stateroom is designed for comfort. Luxurious Egyptian cotton linens wrap you in pleasant sleepiness as you stretch out in your queen bed (can be separated into twins if you prefer). Your spacious bath features granite counter tops, ample storage, and a roomy shower with massage shower head. L’Occitane® bath products invite you to indulge, while comfy waffle-weave robe and slippers entice you to relax. You’ll find fresh fruit and flowers always waiting for you after a day of sun or sightseeing. And, of course, everything else you need and expect — flat-screen television and DVD, private safe. And always at your fingertips, anything you wish from room service.
? Cruise only from $6,049 per guest
? All-inclusive price from $6,049 per guest
Owner's Suite
Owner's Suite
With an expansive 220 square feet, the Owner’s Suite gives you everything offered in a stateroom, plus lots more, including a beautiful sitting area and separate in-room dining space.
? Cruise only from $8,499 per guest
? All-inclusive price from $8,499 per guest
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
Watersports Platform
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session
ALL DATES &
FARES
Early Booking Offer 2026
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited beer, wine, and cocktails, and gratuities. From $89 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Thu, Jun 4 - Thu, Jun 11, 2026
WIND SPIRIT
$5,399
$5,399
Thu, Jun 18 - Thu, Jun 25, 2026
WIND SPIRIT
$4,999
$4,999
THIS
SAILING
Thu, Sep 10 - Thu, Sep 17, 2026
WIND SPIRIT
$5,299
$5,299
Thu, Sep 24 - Thu, Oct 1, 2026
WIND SPIRIT
$5,299
$5,299