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Off The Beaten Path Greek Islands
Jun 4, 2026 — Jun 11, 2026
Starting from
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.





Popular Highlights
Walk to the Panagia Church in Folegandros, Greece to get stunning view of the Aegean Sea.
Take a tour in Milos, Greece to see the lunar-like landscape, created by a volcanic eruption over 2 million years ago.
Visit Ermoupoli, a beautiful town with a strong Venetian influence known for its neoclassical architecture, colorful buildings, and narrow streets.
From Naxos, Greece, explore Apeiranthos Village, a traditional mountain village known for its well-preserved architecture, marble-paved streets, and scenic views.
Late night stays in Kusadasi, Naxos, and Folegandros allow for plenty of time to explore before returning back to your ship.
On Samos, explore charming villages like Kokkari and Pythagoreio, each offering a blend of traditional architecture and bustling harbors.

Complimentary Windstar 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 4-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.
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.

Complimentary Windstar 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 4-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.
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.
Ermoupoli, Transfer to Kini Beach *


Ermoupoli, Transfer to Kini Beach *
Board your waiting motor coach for the 30-minute drive ti Kini Beach. Wear your swimsuit under your clothing; bring a towel, sunscreen and a hat. You will spend approximately 3 hours enjoying this lovely beach exactly as you please. The beach is wide and sandy with shallow water. Taverns and cafes are also available. Please note: Sunbeds and umbrellas are reserved beforehand. They may not be first on the waterfront.
Ermoupoli, Highlights of Syros *


Ermoupoli, Highlights of Syros *
During the 19 th century Ermoupoli was Greece's principal port and stands on a natural amphitheater site. You will board your motor coach that will take you from the port up the long, steep hill to the top where you will see the Cathedral of St. George. You will visit this 14 th century building before descending on foot to pass by the Cappuchin Monastery of St. John. Continue your descent to the bottom of the hill and re-board your coach for the drive across the island. You will pass the villages of Vari and Chroussa and reach the village of Posidonia. You will see the outside of the Tsiropina Mansion, a building that used to belong to one of the most renowned families in Greece and used to serve as the Town Hall. Next you will travel to the seaside village of Finikas where you will stop for refreshments. Continue on your scenic drive through the villages of Galissas and Talanta on your way back to Ermoupoli. Here your guide will take you on a walking tour visiting the main sites of this beautiful town. Please note: Wear comfortable walking shoes. This tour is not wheelchair accessible.
Syros: Syros Walking tour & Cooking Demo *


Syros: Syros Walking tour & Cooking Demo *
Enjoy your guided walk of Ermoupouli, the main town of Syros island and capital of Cyclades group of islands. Vist the impressive Church of St. Nicholas, the Vaporia quarter with its neoclassical mansions, and the Monument of the Unknown Soldier. Conclude your tour at a local traditional restaurant were the owner will let you in on some of the secrets behind some of her traditional recipees followed by lunch. Afterwards, you can either walk back to the yacht with your guide or time permitting may choose to remain in town for some leisure time and stroll back to the yacht at your own pace. Please note: This tour involves some walking and standing. Guests with limited mobility should take this into consideration. Dietary requirements can be accommodated but need to be communicated 48 hours prior to call. Wear sunscreen and anti-slip shoes, bring a hat and local currency.
Kusadasi, Concierge Collection: Full Day Private VAN + Guide *


Kusadasi, Concierge Collection: Full Day Private VAN + Guide *
Explore at your leisure with a private vehicle, driver and English-speaking guide. This exclusive tour will allow you to customize your time ashore and explore the most interesting sites in the comfort and privacy of your own van. With your private vehicle, and the personalized attention of your driver and English-speaking guide, you will have the flexibility and independence to design your itinerary ashore . See the iconic sites of the city, or create your own personal stops to make the experience your own. Please note : Capacity: 1-10 guests. Private vans are ordered per vehicle (not per person). This tour includes transport in a private van, driver and English Speaking Guide. Itinerary can be adjusted with tour guide as long as it's in the area and does not exceed the duration of 8 hours. Recommended for physically challenged guests.
Kusadasi, Concierge Collection: Full Day Private Car + Guide
Kusadasi, Concierge Collection: Full Day Private Car + Guide
No additional details available for this excursion.
Kusadasi, Concierge Collection: Half Day Private Car + Guide
Kusadasi, Concierge Collection: Half Day Private Car + Guide
No additional details available for this excursion.
Kusadasi, Ephesus & Ancient Houses *


Kusadasi, Ephesus & Ancient Houses *
Ancient Ephesus, a UNESCO World Heritage Site, is one of the greatest outdoor museums in Turkey and perhaps in the world. Although now in ruins, it was originally founded by the Carian and Leleg native peoples. Your two-hour walking tour begins after a 30-minute drive from the pier. Magnificent vistas await - including the glorious Celsus Library façade, the Grand Amphitheater and the Temple of Hadrian . The Terrace Houses owned by the wealthy and influential lie opposite Hadrian's Temple, in a newly excavated section. Their fine decorative mosaics and frescoes give a fascinating insight into ancient lifestyles. Terrace Houses on the slopes of Bulbul Mountain are accessed by steps, with their roofs forming terraces for those houses above them. Back in Kusadasi, there's an opportunity to see a carpet-making demonstration , to independently explore the town or perhaps browse among the shops before taking an easy stroll back to the ship. Please note: As this excursion involves extensive walking, comfortable shoes with non-slip soles are recommended. At Terrace Houses, guests will walk on glass-covered platforms.
Kusadasi, Best of Ephesus *


Kusadasi, Best of Ephesus *
The first place you will visit on this exciting tour will be the Virgin Mary's House . Archaeological evidence shows that the little house dates from the 6th century but that the foundations were from the first century. Next you will visit the Ephesus ruins, a UNESCO World Heritage Site predominantly from the later Roman period. Next, you will visit the Ephesus Archaeological Museum. This small museum in Selcuk boasts an incredible collection of Hellenistic and Roman statues, carved reliefs and artifacts unearthed from the ruins of Ephesus. The famous statue of Artemis (goddess of fertility) is housed here. Then, your tour will continue to the ruins of the Basilica of St John . The Basilica had a cruciform plan with four domes along its longitudinal axis and a pair flanking the central dome to form the arm of the cross. Under the central dome was the grave of St John. Lunch will be served at a lovely local restaurant on the way back to Kusadasi. You will have a fabulous view of the harbor and the ship.Upon your return to Kusadasi, you may enjoy a carpet weaving demonstration and some time for shopping . Explore the town and return to the ship. Please note : There is a lot of walking on this tour with many steps and rough and uneven terrain. Flat, comfortable shoes are highly recommended. The last 3 miles to the Virgin Mary's House is a winding road up to an altitude of 1,250 feet.
Kusadasi, Concierge Collection: Full Day Private VAN + Guide *


Kusadasi, Concierge Collection: Full Day Private VAN + Guide *
Explore at your leisure with a private vehicle, driver and English-speaking guide. This exclusive tour will allow you to customize your time ashore and explore the most interesting sites in the comfort and privacy of your own van. With your private vehicle, and the personalized attention of your driver and English-speaking guide, you will have the flexibility and independence to design your itinerary ashore . See the iconic sites of the city, or create your own personal stops to make the experience your own. Please note : Capacity: 1-10 guests. Private vans are ordered per vehicle (not per person). This tour includes transport in a private van, driver and English Speaking Guide. Itinerary can be adjusted with tour guide as long as it's in the area and does not exceed the duration of 8 hours. Recommended for physically challenged guests.
Kusadasi, Concierge Collection: Half Day Private VAN + Guide *


Kusadasi, Concierge Collection: Half Day Private VAN + Guide *
Explore at your leisure with a private vehicle, driver and English-speaking guide. This exclusive tour will allow you to customize your time ashore and explore the most interesting sites in the comfort and privacy of your own van. With your private vehicle, and the personalized attention of your driver and English-speaking guide, you will have the flexibility and independence to design your itinerary ashore. See the iconic sites of the city, or create your own personal stops to make the experience your own. Please note : Capacity: 1-10 guests. Private vans are ordered per vehicle (not per person). This tour includes transport in a private van, driver and English Speaking Guide. Itinerary can be adjusted with tour guide as long as it's in the area and does not exceed the duration of 4 hours. Recommended for physically challenged guests.
Kusadasi, Concierge Collection: Ephesus & Private Lunch at Sirince Village *


Kusadasi, Concierge Collection: Ephesus & Private Lunch at Sirince Village *
Visit the ruined city of ancient Ephesus , a UNESCO World Heritage Site, founded by the Carians and Lelegs. You will see the glorious Celsus Library façade, restored and reconstructed in the 1970s, the Grand Amphitheater and the Temple of Hadrian. Visit the "Terrace Houses" located opposite Hadrian's Temple, a newly excavated area. Next you will discover the beauty of Sirince Village , the perfect synthesis of Turkish-Greek culture where you will stroll through the streets and see the typical Greek houses. You will have time to purchase some local handicrafts that the village ladies sell on the streets. The tour features a charming church dedicated to St John that you can view high above the village. A private lunch has been arranged for you in a beautifully restored local building, with spectacular views overlooking an amazing valley of fruit and olive trees and lots of grapevines. Here you will experience the local cuisine with the best of Turkish hospitality. Taste a few of the local wines throughout your private lunch . Upon your return to Kusadasi, you may enjoy a carpet-making demonstration and have some time for shopping. Explore the town and return to the yacht on your own. Please note : This tour involves a great deal of walking over uneven terrain. Comfortable walking shoes are highly recommended.
Kusadasi, Archaeological Ephesus & Museum *


Kusadasi, Archaeological Ephesus & Museum *
Meet your professional guide and set off to visit the ruined city of ancient Ephesus, a UNESCO World Heritage Site founded by the Carians and Lelegs. Today, this is one of the most magnificent and best-preserved archaeological sites in the world. You will see the glorious Celsus Library façade, restored and reconstructed in the 1970s, the Temple of Hadrian , and the Great Theatre with a seating capacity of 25,000 people. You will also visit the Ephesus Archaeological Museum . This small museum in Selcuk boasts an incredible collection of Hellenistic and Roman statues, carved reliefs and artifacts unearthed from the ruins of Ephesus. The famous statue of Artemis (goddess of fertility) is housed here. At the end of your tour, you will stop for refreshments and a carpet demonstration at a local weaving village. Enjoy watching the skilled artisans spinning and dyeing yarn and weaving carpets. From here you can either return directly to the ship or stay in Kusadasi. Guests who wish to stay in town to shop or explore on their own are welcome to do so, but must return to the ship on their own. Please note : This tour involves a great deal of walking over uneven terrain. Comfortable walking shoes with non-skid soles are highly recommended.
Kusadasi, Ephesus and Virgin Mary's House


Kusadasi, Ephesus and Virgin Mary's House
Take a step back in time on this excursion to the Virgin Mary's House and ancient Ephesus, a UNESCO World Heritage Site. A 30-minute drive will bring you to the House of the Virgin Mary, where she is said to have lived the last years of her life. This hallowed site, which has been officially declared a Roman Catholic shrine, has hosted three Papal visits since 1967. Then you will take a 10-minute drive to Ephesus, where you will see with the Odeon Theatre , the Celsus Library and Hadrian Temple. This impressive Corinthian-style temple was dedicated in A.D. 118 and reconstructed in the 4th century. You will see the Great Theatre, dating back to the Hellenistic period. It was at this monumental site that St. Paul preached. As its acoustics remain excellent, this theatre is still in use today. The Marble Road which runs between the Theater and the Celsus Library is part of a sacred walkway. On your return, you will sip apple tea as a myriad of colors unfold before your eyes during a carpet-making demonstration. Or, you may return directly to the yacht, or remain in Kusadasi to shop or explore the town independently. Please note : Although there are no uphill surfaces, this excursion does involve extensive walking. Comfortable walking shoes with non-slip soles are therefore recommended.
Naxos, Walking Tour *


Naxos, Walking Tour *
Chora, on the west coast, is the island's port and capital. It is a large town divided in two historic neighborhoods - Bourgos where the Greeks lived and Kastro where the Venetian Catholics lived. Kastro is the most alluring part of the town with winding alleyways and white-washed houses. A causeway to the north of the port leads to the islet of Palatia and the unfinished Temple of Apollo, Naxos' most famous landmark (also known as Portara). After visiting the temple, you will walk back to the Kastro area. Walking in the Kastro you will be able to admire the Orthodox Cathedral, the Catholic Cathedral and the Archaeological Museum. The museum includes collections of vases and torsos as well as Hellenistic and Roman terraccota figurines. There are also some early Cycladic figurines. You will also have the opportunity to walk through the narrow streets where there are some handsome Venetian dwellings, many with well kept gardens and insignia of their original residents. Please note : The walking tour involves covering a considerable distance over narrow cobblestone streets with uphill sections. There is a total of approximately 60 steps to be negotiated . Not suitable for guests with walking difficulties. Wear comfortable walking shoes.
Naxos, Traditional Villages of Naxos *


Naxos, Traditional Villages of Naxos *
Naxos is the largest and most fertile of the Cycladic Islands. Departing from the port, you will head towards the central area of the island where Chalki, the old capital of Naxos, is located. There, you will visit a distillery of citron, a local liqueur distilled from lemons. Carrying on again, you will stop to visit the church of Panagia Drosiani (6th cent. AD) near the village of Moni, one of the best preserved monuments from the Early Christian era. You will pass through the village of Filoti, the island's largest village and former Frankish fief on your way to Apiranthos, the island's oldest village. There, you will have the chance to visit the archaeological, the geological, the folkloric and the museum of the history of nature, depending on your interests. Apiranthos is a village which has retained its traditional appearance with its very narrow streets, paved with marble, beautiful 2-story houses built from local stone, sloping alleys, Venetian towers and charming little cafés. Your last stop before returning to the port will be the village of Melanes, where a large unfinished 6 th century BC Kouros (male statue) lies abandoned. Please note: Wear comfortable walking shoes.
Naxos, Hidden Coves & Island Charms: Private Cruise Naxos-Paros
Naxos, Hidden Coves & Island Charms: Private Cruise Naxos-Paros
No additional details available for this excursion.
Folegandros, An Aegean Evening on Folegandros
Folegandros, An Aegean Evening on Folegandros
No additional details available for this excursion.
Folegandros, Folegandros by Sea: Hidden Bays & Crystal Waters
Folegandros, Folegandros by Sea: Hidden Bays & Crystal Waters
No additional details available for this excursion.
Folegandros, Traditions of Folegandros: A journey through local life
Folegandros, Traditions of Folegandros: A journey through local life
No additional details available for this excursion.
Milos, Concierge Collection: Full Day Private Car with Guide *


Milos, Concierge Collection: Full Day Private Car with Guide *
Explore at your leisure with a private vehicle, driver, and English-speaking guide. This exclusive tour will allow you to customize your time ashore and explore the most interesting sites in the comfort and privacy of your own car. With your private vehicle, and the personalized attention of your driver and English-speaking guide, you will have the flexibility and independence to design your itinerary ashore. See the iconic sites of the city, or create your own personal stops to make the experience your own. Please note : Capacity: 1-2 guests. Private cars are ordered per vehicle (not per person). This tour includes transport in a private car, driver and English Speaking Guide. Itinerary can be adjusted with tour guide as long as it's in the area and does not exceed the duration of 8 hours. Recommended for physically challenged guests.
Milos, Concierge Collection: Half Day Private Car with Guide *


Milos, Concierge Collection: Half Day Private Car with Guide *
Explore at your leisure with a private vehicle, driver, and English-speaking guide. This exclusive tour will allow you to customize your time ashore and explore the most interesting sites in the comfort and privacy of your own car. With your private vehicle, and the personalized attention of your driver and English-speaking guide, you will have the flexibility and independence to design your itinerary ashore. See the iconic sites of the city, or create your own personal stops to make the experience your own. Please note : Capacity: 1-2 guests. Private cars are ordered per vehicle (not per person). This tour includes transport in a private car, driver and English Speaking Guide. Itinerary can be adjusted with tour guide as long as it's in the area and does not exceed the duration of 4 hours. Recommended for physically challenged guests.
Milos, Amazing Beach *


Milos, Amazing Beach *
This is a tour set-up to visit one of the nicest beaches of the island. Your escort will assist you during this trip and you will visit the beach of Paleochori - sunbeds and umbrellas are included. You will have 3 hours to relax and enjoy this lovely location. Please note : Wear comfortable walking shoes, sunglasses and sunscreen. Bring a hat, your swimsuit and a towel.
Milos Highlights *


Milos Highlights *
Volcanic Milos, the most westerly island of the Cyclades has stunning beaches, coves, and geologically interesting places. Since antiquity the island has been quarried for its minerals. Obsidian, a hard, black volcanic glass used for manufacturing sharp blades was mined on the island and exported throughout the Mediterranean. You will visit the Sarakiniko Beach with its lunar landscape, the result of volcanic eruptions. This beautiful, moon-like spot is one of the island's many geological wonders and perhaps one of the most photographed places in the Cyclades. You'll take a walk down the beach so you can experience this one-of-a-kind location and take photographs. Next you will visit the cave of Papafragkas, a cluster of deep-sea inlets and sea caves. Located next to Papafragkas Cave is Filakopi, a settlement dating back to the Neolithic Period (approximately 9,000 to 4,000 B.C.) and remained an active settlement until 1,000 B.C. From Papafragkas you can see the remains of the walls of the city (only standing remains of the city at this point). The tour does NOT enter the archaeological site. Next stop Plak a and its cobble streets and alleys. Plaka is a classic Cycladic village with white stone houses and bougainvillea flowers, locted on a hilltop. You'll walk through the village to admire its traditional architecture and its stunning view of the sea, and you'll taste some homemade sweets at the village's local pastry shops at your leisure. Following, the Christian Catacombs , which are the largest in Greece, and the ruins of the ancient city of Klima . Close to the Catacombs is the marble amphitheater. There are still seven intact seat rows and there is a lovely view of the bay. On the way to the theater from the Catacombs, you will also visit the site where Venus de Milo was discovered in 1820 (now residing in the Louvre in Paris). Please note : Wear comfortable walking shoes, sunglasses and sunscreen.
Staterooms
Staterooms description here
Starting from
Amenities
- Queen Size Bed with Luxurious Linens
- Fully-Stocked Mini Bar/Refrigerator
- L'Occitane Bath Amenities
- Fresh Fruit
- Hair Dryers and 110/220 Outlets
- Waffle Weave Robe and Slippers
- Safe
- Granite Vanity with Magnifying Mirror
- Bathroom with Granite Countertop and Shower
- Wi-Fi (internet cards can be purchased at reception)
- TV with DVD Player
Category AX Deluxe
Every inch of your 188 square feet 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.
Starting from
Amenities
- Queen Size Bed with Luxurious Linens
- Fully-Stocked Mini Bar/Refrigerator
- L'Occitane Bath Amenities
- Fresh Fruit
- Hair Dryers and 110/220 Outlets
- Waffle Weave Robe and Slippers
- Safe
- Granite Vanity with Magnifying Mirror
- Bathroom with Granite Countertop and Shower
- Wi-Fi (internet cards can be purchased at reception)
- TV with DVD Player
Category A
Every inch of your 188 square feet 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.
Starting from
Amenities
- Queen Size Bed with Luxurious Linens
- Fully-Stocked Mini Bar/Refrigerator
- L'Occitane Bath Amenities
- Fresh Fruit
- Hair Dryers and 110/220 Outlets
- Waffle Weave Robe and Slippers
- Safe
- Granite Vanity with Magnifying Mirror
- Bathroom with Granite Countertop and Shower
- Wi-Fi (internet cards can be purchased at reception)
- TV with DVD Player
Category BX Deluxe
Every inch of your 188 square feet 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.
Starting from
Amenities
- Queen Size Bed with Luxurious Linens
- Fully-Stocked Mini Bar/Refrigerator
- L'Occitane Bath Amenities
- Fresh Fruit
- Hair Dryers and 110/220 Outlets
- Waffle Weave Robe and Slippers
- Safe
- Granite Vanity with Magnifying Mirror
- Bathroom with Granite Countertop and Shower
- Wi-Fi (internet cards can be purchased at reception)
- TV with DVD Player
Category B
Every inch of your 188 square feet 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.
Available Dates
| Date | Yacht | Starting from | Actions |
|---|---|---|---|
| Jun 18 (Thu) – Jun 25 (Thu), 2026June 18 (Thu) – June 25 (Thu), 2026 | Wind Spirit | $13,528 | |
| Sep 24 (Thu) – Oct 1 (Thu), 2026September 24 (Thu) – October 1 (Thu), 2026 | Wind Spirit | $15,528 |