Off The Beaten Path Greek Islands

Jun 4, 2026 — Jun 11, 2026

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PIRAEUS, ATHENS → PIRAEUS, ATHENS

7 Nights on Wind Spirit

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.

Complimentary Windstar Destination Discovery Event

Complimentary Windstar Destination Discovery Event

Evening in Ephesus

Join us for a once-in-a-lifetime experience after hours during this Evening in Ephesus event exclusive to Windstar guests on this and other select voyages. 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: Evening in Ephesus 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.

1
JUN 04, 2026
Athens, Greece
EMBARK
1:00 PM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
2

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. 

Athens, Acroplolis Museum & Scenic Tour Transfer to Airport

Time
8:00 AM
Duration
4 Hours
Activity Level
Strenuous
Price
$149

Athens, Acropolis Museum & Scenic Tour Transfer to WSC Hotel

Time
8:30 AM
Duration
3 Hours
Activity Level
Strenuous
Price
$149
2
JUN 05, 2026
Ermoupoli
ARRIVE
7:00 AM
DEPART
4:00 PM
MARINA
NO
SHORE EXCURSIONS
3

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.

Syros: Syros Walking tour & Cooking Demo *

Time
7:30 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$219

Ermoupoli, Transfer to Kini Beach *

Time
7:45 AM
Duration
4 Hours
Activity Level
Easy-Moderate
Price
$115

Ermoupoli, Highlights of Syros *

Time
7:30 AM
Duration
4.5 Hours
Activity Level
Strenuous
Price
$119
3
JUN 06, 2026
Kusadasi
ARRIVE
8:00 AM
DEPART
11:59 PM
MARINA
NO
SHORE EXCURSIONS
10

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.  

Kusadasi, Archaeological Ephesus & Museum *

Time
8:30 AM
Duration
5 Hours
Activity Level
Moderate
Price
$99

Kusadasi, Concierge Collection: Full Day Private Car Guide

Time
9:01 AM
Duration
8 Hours
Activity Level
Easy
Price
$699

Kusadasi, Concierge Collection: Full Day Private VAN + Guide *

Time
8:30 AM
Duration
8 Hours
Activity Level
Easy
Price
$899

Kusadasi, Concierge Collection: Ephesus & Private Lunch at Sirince Village *

Time
9:00 AM
Duration
7 Hours
Activity Level
Moderate-Strenuous
Price
$169

Kusadasi, Best of Ephesus *

Time
8:30 AM
Duration
7.5 Hours
Activity Level
Moderate-Strenuous
Price
$159

Kusadasi, Ephesus and Virgin Mary's House

Time
8:30 AM
Duration
5 Hours
Activity Level
Moderate
Price
$99

Kusadasi, Concierge Collection: Full Day Private VAN + Guide *

Time
9:01 AM
Duration
8 Hours
Activity Level
Easy
Price
$899

Kusadasi, Concierge Collection, Half Day Private Car & Guide

Time
9:01 AM
Duration
4 Hours
Activity Level
Easy
Price
$599

Kusadasi, Concierge Collection: Half Day Private VAN + Guide *

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$699

Kusadasi, Ephesus & Ancient Houses *

Time
8:45 AM
Duration
4 Hours
Activity Level
Moderate-Strenuous
Price
$99
4
JUN 07, 2026
Pythagoreio, Greece
ARRIVE
7:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
4

TBA

Phythagorieo Samos, Samos Beach Escape

Time
9:30 AM
Duration
4 Hours
Activity Level
Easy-Moderate
Price
$119

Phythagorieo Samos, From Hera to Harvest the Story of Samos

Time
8:00 AM
Duration
5 Hours
Activity Level
Easy-Moderate
Price
$179

Phythagorieo Samos, Samos Stories Sacred Views. Historic, Streets & Local Wines

Time
8:30 AM
Duration
4.5 Hours
Activity Level
Easy-Moderate
Price
$99

Phythagorieo Samos, Secrets Beneath Samos Eupalinus Tunnel Archaeological Museum

Time
8:45 AM
Duration
4 Hours
Activity Level
Moderate
Price
$169
5
JUN 08, 2026
Naxos, Greece
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
3

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.

Naxos, Walking Tour *

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$95

Naxos, Traditional Villages of Naxos *

Time
8:30 AM
Duration
4.5 Hours
Activity Level
Moderate
Price
$149

Naxos, Hidden Coves & Island Charms: Private Cruise Naxos-Paros

Time
8:30 AM
Duration
6.25 Hours
Activity Level
Easy
Price
$329
6
JUN 09, 2026
Folegandros, Greece
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
3

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.

Folegandros, An Aegean Evening on Folegandros

Time
6:30 PM
Duration
2.5 Hours
Activity Level
Easy
Price
$299

Folegandros, Folegandros by Sea: Hidden Bays & Crystal Waters

Time
8:30 AM
Duration
6 Hours
Activity Level
Easy-Moderate
Price
$229

Folegandros, Traditions of Folegandros: A journey through local life

Time
8:30 AM
Duration
3 Hours
Activity Level
Easy
Price
$199
7
JUN 10, 2026
Milos, Greece
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
YES
SHORE EXCURSIONS
4

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

Milos, Concierge Collection: Full Day Private Car with Guide *

Time
8:30 AM
Duration
8 Hours
Activity Level
Easy
Price
$1499

Milos Highlights *

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy-Moderate
Price
$119

Milos, Concierge Collection: Half Day Private Car with Guide *

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$1099

Milos, Amazing Beach *

Time
9:15 AM
Duration
4 Hours
Activity Level
Easy
Price
$115

Wind Spirit

number of decks
4 Decks
yacht length
360 ft (110 meters)
yacht crew size
90 Crew Members
yacht guest capacity
148 Guests

Staterooms

Room Size 188 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 188 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 220 sq ft
Max. Occupancy 3 Passengers
Amenities

Room Size 188 sq ft
Max. Occupancy 2 Passengers
Amenities

Room Size 188 sq ft
Max. Occupancy 2 Passengers
Amenities

Room Size sq ft
Max. Occupancy 2 Passengers
Amenities