Off The Beaten Path Greek Islands

Sep 24, 2026 — Oct 1, 2026

Starting from $10,928 Displayed pricing is based off of double occupancy per person. Pricing subject to change based on occupancy and cabin selection.

See more routes around Greece

PIRAEUS, ATHENS → PIRAEUS, ATHENS

7 Nights in Wind Spirit

1
SEP 24, 2026
Athens, Greece
EMBARK
1:00 PM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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. 

2
SEP 25, 2026
Milos, Greece
ARRIVE
7:00 AM
DEPART
10:00 PM
MARINA
NO
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
7:30 AM
Duration
8 Hours
Activity Level
Easy
Price
$1365

Milos Highlights *

Time
7:30 AM
Duration
4 Hours
Activity Level
Easy-Moderate
Price
$115

Milos, Amazing Beach *

Time
7:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$109

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

Time
7:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$945
3
SEP 26, 2026
Folegandros, Greece
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
2

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.

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

Time
10:30 AM
Duration
8 Hours
Activity Level
Easy
Price
$899

Kusadasi, Windstar Destination Discovery Event

Time
5:00 PM
Duration
3 Hours
Activity Level
Easy
Price
N/A
4
SEP 27, 2026
Naxos, Greece
ARRIVE
7:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
2

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, Traditional Villages of Naxos *

Time
7:30 AM
Duration
4.5 Hours
Activity Level
Moderate
Price
$125

Naxos, Walking Tour *

Time
7:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$95
5
SEP 28, 2026
Pythagoreio, Greece
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
0
6
SEP 29, 2026
Kusadasi
ARRIVE
8:00 AM
DEPART
11:00 PM
MARINA
NO
SHORE EXCURSIONS
6

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, Best of Ephesus *

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

Kusadasi, Ephesus & Ancient Houses *

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate-Strenuous
Price
$99

Kusadasi, Archaeological Ephesus & Museum *

Time
8:30 AM
Duration
5 Hours
Activity Level
Moderate
Price
$89

Kusadasi, Ephesus and Virgin Mary's House

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

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

Time
8:30 AM
Duration
7 Hours
Activity Level
Moderate-Strenuous
Price
$149

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

Time
8:30 AM
Duration
8 Hours
Activity Level
Easy
Price
$899
7
SEP 30, 2026
Ermoupoli
ARRIVE
12:30 PM
DEPART
6:00 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.

Ermoupoli, Highlights of Syros *

Time
1:00 PM
Duration
4.5 Hours
Activity Level
Strenuous
Price
$99

Ermoupoli, Transfer to Kini Beach *

Time
1:00 PM
Duration
4 Hours
Activity Level
Easy-Moderate
Price
$89

Syros: Syros Walking tour & Cooking Demo *

Time
1:00 PM
Duration
3.5 Hours
Activity Level
Moderate
Price
$199

Wind Spirit

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

Available Staterooms

Category B

Cabin
13 Cabins
Max. Occupancy
3 Passengers
Room Size
1 Sqft
Amenities

Category A

Cabin
12 Cabins
Max. Occupancy
2 Passengers
Room Size
1 Sqft
Amenities

Category AX Deluxe

Cabin
24 Cabins
Max. Occupancy
2 Passengers
Room Size
1 Sqft
Amenities

Category BX Deluxe

Cabin
24 Cabins
Max. Occupancy
3 Passengers
Room Size
1 Sqft
Amenities

Available Dates