What becomes immediately apparent aboard a Windstar yacht is just how differently the Greek islands appear on a cruise. Not from the crowded upper deck of a towering ship, but from the teak-lined terrace of a small sailing yacht carrying just 148 guests. Santorini appears slowly through the morning haze, whitewashed villages suspended above volcanic cliffs. In Patmos, fishing boats drift lazily across the harbour long after breakfast has finished. By evening, the sails unfurl overhead as the coastline dissolves into gold beneath the fading sun.
Somewhere between the first alfresco lunch on deck and a late evening wandering through the narrow lanes of buzzing Mykonos, the usual rhythm of travel begins to loosen. There are no frantic port arrivals or crowded buffet halls here. Windstar Cruises approaches the Mediterranean differently, favouring intimacy over spectacle and atmosphere over excess. On its seven-day Treasures of the Greek Isles itinerary, that philosophy feels perfectly suited to the Aegean itself.
The sea changes everything. Even the way you arrive.
The Windstar Difference
For decades, Windstar Cruises has occupied a unique corner of the luxury cruise world. Its fleet of small yachts and sailing vessels offers a far more personal experience than larger cruise brands, both onboard and ashore. Rather than attempting to recreate a floating resort, Windstar leans into the romance of traditional sailing, creating voyages that feel elegant without becoming overly formal. This is represented by our fellow guests, who ranged from couples, families, groups and single travellers.
Wind Star, the yacht that first launched the brand in 1984, still retains the atmosphere that made it so distinctive in the first place. Four towering masts rise above wide-open teak decks, while six enormous computer-operated sails stretch overhead across more than 21,000 square feet. The result feels cinematic rather than performative, particularly at sail-away, when Vangelis echoes softly across the deck as the sails unfurl into the evening sky.
It is difficult not to pause for a moment when it happens.
The yacht itself feels closer to a private vessel than a traditional cruise ship. With just 73 ocean-view staterooms, one Owner’s Suite and 105 brilliant crew members onboard, the experience quickly becomes familiar in the best possible way. Bartenders remember how you take your drink. Crew members greet guests by name. Familiar faces begin appearing at breakfast each morning as the coastline changes outside the windows.
The smaller scale of the yacht changes the entire dynamic of the experience. There is no sense of being carelessly processed through destinations. Much of the excess commonly associated with large-scale cruising simply disappears. Instead, we arrive directly into the heart of smaller harbours and island towns that larger ships simply cannot access. It is that sweet spot for travellers who care about the journey and the destination equally and do not wish to compromise on either. The result is a voyage that feels considerably more connected to the places themselves, and far more personal. Travel begins to feel slower and more considered, as though the journey itself matters just as much as the destination.
Life Onboard
Life aboard Wind Star settles naturally into its own rhythm. Days begin slowly with breakfast served on the open deck, sunlight reflecting off the water while the yacht glides towards another island harbour. Fresh pastries and espresso beneath the soft morning sun, accompanied only by the calm movement of the sea, feels like an excursion in itself rather than simply breakfast before another destination. Some mornings are spent beside the pool with a book, others watching the sails overhead from the upper deck as the Aegean stretches endlessly into the distance.
The yacht underwent a significant redesign as part of Windstar’s Setting Sails initiative, though the interiors remain intentionally understated. Polished wood panelling, warm lighting and soft nautical detailing give the spaces a sense of comfort rather than formality. Nothing feels cluttered or overly designed, yet the feeling of luxury is unmistakable.
The staterooms follow that same approach. Compact yet thoughtfully arranged, they feel more akin to a boutique hotel than a traditional cruise cabin. Queen-sized beds dressed in crisp linens sit beside cosy lounge seating, while walk-in wardrobes, L’Occitane amenities, granite vanities and ocean views make the space feel both practical and indulgent. After long days ashore, returning to the room each evening carries the familiar comfort of returning somewhere genuinely lived in.
At sea, it becomes the small rituals you remember most.
Coffee arriving just as the coastline appears at sunrise. Salt drying on the railings after an afternoon swim from the yacht’s marina platform. A chilled glass of wine brought to the table before you even think to order it.
Afternoons onboard drift easily between the yacht’s intimate spa, modern fitness studio, teak-lined upper deck and the marina platform at the back of the vessel, where we can swim directly into the Aegean while anchored offshore. This marina was such a highlight. There were stand-up paddle boards and inflatable seating areas as well as a mini swimming pool created in the sea. The smaller scale of the yacht creates an atmosphere that feels noticeably more relaxed than traditional cruising. There are no queues, no overcrowded lounges and no pressure to constantly fill the day with activity. Instead, life onboard unfolds slowly and naturally.
Dining and Evenings at Sea
Dining forms a central part of the experience. Windstar’s partnership with the James Beard Foundation brings a strong culinary focus to the voyage, with menus inspired by the destinations visited throughout the itinerary. One evening might bring grilled branzino with lemon beurre blanc and local olive oil, another slow-cooked lamb beneath the open sky at Candles, while Mediterranean ingredients sourced throughout the journey appear across the menus in quietly thoughtful ways.
Fresh seafood, seasonal vegetables, authentic feta, Greek olive oils and local wines feature prominently across the yacht’s open-seating restaurants, whether enjoying dinner inside the softly lit Amphora restaurant, dining beneath the stars at Candles or lingering over lunch at Veranda as islands drift by beyond the deck. We experienced Candles on one night and it was sensational. The area is transformed into an outdoor steakhouse, so expect prawns, fillet steak and proper onion rings. On another night there was a BBQ on the deck, which was transformed by the hard-working team into a full outdoor restaurant.
There is something particularly enjoyable about returning from a long afternoon ashore to find dinner unfolding slowly beneath the open sky, glasses clinking softly as the yacht rocks gently offshore. By the second evening, bartenders at the yacht’s intimate pool bar already know which cocktail we want to order before dinner, while sunset cocktails begin appearing across the upper deck as islands fade into silhouette.
The drinks package is really worth it and gives you the freedom to enjoy a lot of premium options and not worry about the cost. The cocktail list was impressive, but the team can also make anything you like – you just need to ask. Something we found really valuable and luxurious was the coffee shop. Tucked away near the lounge, the coffee shop had a superb choice of drinks and snacks throughout the day, from the Greek yogurt bowls to the awesome cookies. Unlike larger cruise ships where you wait in line for your coffee fix, this was never an issue here.
Evenings onboard remain deliberately understated. There are cocktails beneath the stars, live music drifting softly through the lounge and conversations that continue long after dinner has finished. The yacht never relies on excess entertainment or constant activity to hold attention. Instead, the luxury lies in simplicity, authenticity and atmosphere.
The entertainment on a daily basis was so engaging and fun – very talented singers entertained us throughout. A dynamic husband and wife duo called Purple Sundaze. A real highlight was the staff talent show which showcased the brilliant team onboard.
Day One: Athens and the Beginning of the Voyage
The journey begins in Athens, where we board in Piraeus before sailing into the Cyclades. With more than 3,000 years of history surrounding the city, it feels impossible not to encounter the past at every turn. The Acropolis rises above the skyline, while metro stations display ancient relics uncovered during excavation works beneath the city itself.
As the yacht departs Athens, the city gradually fades into the distance, replaced by open water and scattered islands. The mood onboard noticeably softens as land disappears behind the sails.
Day Two: Mykonos
Mykonos is often the first stop, though arriving aboard a small yacht transforms the experience entirely. Early mornings reveal a calmer side to the island before the crowds arrive. Whitewashed alleyways remain quiet, bougainvillea spills from shaded balconies and waterfront cafés slowly begin setting out chairs beside the harbour.
Fishing boats drift beside glamorous private yachts while the island’s famous windmills overlook the sea beyond.
Excursions range from guided walks through Mykonos Town to visits to nearby Delos, the mythological birthplace of Apollo and one of Greece’s most significant archaeological sites. Wandering through the ruins beneath the Mediterranean sun, it becomes easy to understand why mythology still feels woven into daily life throughout the islands.
Day Three: Kusadasi and Ancient Ephesus
From Greece, the itinerary continues towards Kusadasi on Turkey’s western coast, gateway to the ancient city of Ephesus. Few excursions throughout the Mediterranean rival the scale of this remarkably preserved archaeological site. Marble streets stretch towards the vast Great Theatre while the façade of the Library of Celsus rises dramatically against the afternoon heat.
Walking through Ephesus feels less like visiting ruins and more like briefly stepping into another civilisation entirely.
Yet the most memorable part of the experience begins after sunset.
As daylight fades across the ancient city, tables appear beneath the columns of the Library of Celsus for Windstar’s exclusive Evening in Ephesus event. Candlelight flickers against marble stone while we are served a five-course dinner beneath the night sky accompanied by music from the Aegean Chamber Orchestra.
It is one of those rare travel experiences that manages to feel both grand and deeply personal at the same time. Best of all, the experience was included in the cruise fare.
Day Four: Patmos
Patmos offers a quieter atmosphere, its harbour lined with fishing boats and waterfront tavernas. This was our favourite stop. Beyond its peaceful setting, the island carries deep spiritual significance as the place where Saint John is said to have written the Book of Revelation.
Excursions to the Monastery of Saint John and the Cave of the Apocalypse reveal another side of the Aegean beyond its beaches and postcard scenery. The landscape here feels more rugged, the energy calmer and the atmosphere noticeably more contemplative.
Day Five: Santorini
Santorini arrives with unmistakable drama. Entering the caldera by sea remains one of the most extraordinary arrivals in the Mediterranean, the yacht gliding beneath towering volcanic cliffs crowned with whitewashed villages.
Some say the lost city of Atlantis remains buried somewhere beneath these waters. Looking out across the volcanic coastline, it does not feel entirely impossible.
We spent the day exploring Oia’s narrow lanes, discovering Bronze Age ruins at Akrotiri or lingering over crisp glasses of local Assyrtiko wine as the late afternoon light settles across the cliffs.
This is where small-ship sailing comes into its own. Santorini feels entirely different when approached from the sea.
Day Six: Monemvasia
Some of the itinerary’s most memorable moments emerge in lesser-known ports. Monemvasia, connected to the Peloponnese mainland by a narrow causeway, feels almost suspended in time.
Hidden behind fortified stone walls lies a labyrinth of Byzantine churches, terracotta rooftops and narrow cobbled lanes where bougainvillea tumbles from old balconies. Venetian mansions line the lower town while the ruins of Agia Sophia sit high above the sea.
Wandering through the medieval streets as evening settles across the coastline becomes one of those rare travel moments that lingers long after returning home.
Day Seven: Nafplion
The final stop before returning to Athens is Nafplion, elegant and distinctly Venetian in character. The seaside town unfolds through neoclassical architecture, marble squares and waterfront promenades lined with cafés and orange trees.
Excursions venture inland towards the UNESCO-listed ruins of Mycenae and Epidaurus, though many choose simply to remain within Nafplion itself, lingering over long lunches beside the harbour before slowly making their way back towards the yacht.
Above the town, the imposing Palamidi Castle rises from the cliffs, reached by 999 stone steps carved directly into the rock. The views across the Argolic Gulf are more than worth the climb.
A Different Kind of Greek Islands Experience
What ultimately distinguishes Windstar’s Treasures of the Greek Isles is not simply the destinations themselves, but the way the voyage allows us to experience them. The smaller yacht creates room for spontaneity and stillness alike. Afternoons stretch longer. Sunsets become occasions in themselves. Even the simple act of sailing into a harbour feels more intimate when viewed from the deck of a sailing yacht rather than from the upper floors of a floating city.
Somewhere between the salt carried on the breeze, the sound of sails overhead and the glow of island lights reflecting across the water, the experience begins to feel less like a cruise and more like life temporarily relocated to sea.
And by the final evening onboard, that distinction feels surprisingly important.
To discover more, visit Windstar Cruises
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All Images Courtesy of Windstar Cruises.