Wind Star in Monemvasia, Greece. (Photo Credit: Windstar Cruises)
Sailing aboard the Wind Star, a 148-guest, four-masted sailing yacht, felt more like joining a private club than embarking on a cruise. The open teak decks, spacious staterooms and attentive service created a luxurious yet relaxed atmosphere.
When your daughter turns 18, you want more than a dinner or a gift — you want an experience that deepens your bond and stays with you both forever. For us, that celebration took shape as a one-week, small-ship sailing through the Aegean Sea aboard Windstar Cruises’ Treasures of the Greek Isles itinerary.
This wasn’t just a trip. It was a reset. I fell in love — with Greece, with Windstar, with the thoughtful, vibrant young woman my daughter has become, and with life again. For travel advisors seeking a transformational experience to recommend for milestone-celebrating clients, this itinerary delivers.
Exploring the Greek Isles: Highlights from Each Port
The Treasures of the Greek Isles itinerary begins and ends in Athens, visiting six ports across Greece and Turkey. Each stop told its own story.
Mykonos: Farm-to-Table Flavours and Iconic Alleys
Our first stop was Mykonos, where we visited a traditional farm to learn how local cheese is made, followed by a tasting at a boutique winery. Later, we wandered the storybook alleys, stopped for photos and enjoyed lunch overlooking the sea in Little Venice. Instead of limited taxis, we took the public bus to St. Stefanos Beach — an €8 return tip perfect for independent travellers.
Kusadasi: Stepping Back into Roman History
From Kusadasi, we joined a guided excursion to Ephesus, one of the best-preserved Roman cities in the world, and visited the House of the Virgin Mary, believed to be her final home. That evening, Windstar hosted an exclusive Discovery Event — a private dinner under the stars at the Library of Celsus, complete with a live string orchestra. It was cinematic, emotional and unforgettable — an experience no guidebook could replicate.
For travel advisors seeking a transformational experience to recommend for milestone-celebrating clients, this itinerary delivers. (Photo Credit: Claire Zlobin)
Patmos: Spirituality and Seaside Serenity
Patmos surprised me with its emotional depth. We visited the Cave of St. John, where he is said to have written the Book of Revelation, and explored the island’s monastery before cooling off with a swim beneath whitewashed hillside buildings. Peaceful, spiritual and photogenic, it’s ideal for travellers seeking both history and serenity.
Santorini: Sunrise, Spa Bliss, and Sunset Views
We rose at 5 a.m. to watch the sunrise over Santorini — pure magic. After breakfast, we waited an hour for the classic blue-dome photo, then opted for a spa treatment instead of the black-sand beach. That evening, we dined al fresco on the deck of the Wind Star as the sunset painted the sky. It was a simple moment but one of the most meaningful of our trip.
Monemvasia: Medieval Streets and Olive Oil Delights
Known as the “Gibraltar of Greece,” Monemvasia is a walled medieval village built into a cliff. We visited Liotrivi Olive Oil Estate, made focaccia, sampled fresh-pressed oils and local wine, and wandered through olive groves before swimming below the stone walls. The blend of culture, cuisine and calm made this stop a favourite.
Nafplio: Adventure Meets the Aegean
By Nafplio, we were “ruins-ed out,” so we asked locals where to find the best cliff-jumping beach — my daughter’s final birthday wish. We ended up at Arvanitia Beach, with crystal-clear water and easy rock ledges for diving. Later, she jumped off the back of the ship into the Aegean — laughing, fearless and glowing. That moment alone was worth the entire journey.
Athens: Boutique Comfort Before or After Your Cruise
For clients extending their stay, I highly recommend the Retro Athens Hotel for pre- or post-cruise nights. Located in the heart of the city with Acropolis views, this newly renovated boutique hotel offers comfort, a continental breakfast and convenience — ideal for exploring Athens before or after the voyage.
Why Travel Advisors Should Recommend This Itinerary
Windstar’s Treasures of the Greek Isles is ideal for milestone celebrations such as birthdays, graduations and anniversaries; mother–daughter or parent–child bonding trips; luxury travellers seeking a culturally rich but relaxed itinerary; and guests who want the perks of cruising without the crowds.
With overnight stays in Athens and immersive port experiences, the itinerary offers just enough structure while leaving room for spontaneity. The small-ship format ensures guests feel like VIPs at every step.
For me, this wasn’t just a vacation — it was a transformation. And for your clients, it could be too.
