Greece is best experienced when you have time to linger.
Instead of waking up in a massive cruise terminal with thousands of passengers, imagine approaching a Greek island aboard a small yacht, watching whitewashed villages rise above the Aegean, stepping ashore closer to the heart of the destination, and returning to an intimate ship where the atmosphere feels more like a private yacht than a conventional cruise.
That is the appeal of a Windstar Greece cruise.
Windstar's Greek Islands itineraries combine some of the Mediterranean's most recognizable destinations—including places such as Mykonos, Santorini and Patmos—with smaller or less conventional ports and culturally significant destinations.
Is a Windstar Greece Cruise Worth Considering?
Yes—especially for travelers who value intimacy, destination immersion, relaxed luxury and the experience of sailing aboard a small yacht. Windstar Greece is best understood as a yacht-style way to experience the Greek Islands, rather than a miniature version of a large cruise ship.
Windstar Greece Cruise Highlights
Is Windstar Greece Right For You?
The Romantic & Honeymooner
Couples seeking an intimate Greek Island vacation away from the crowds.
You Enjoy:
- •Values intimacy and romance
- •Prefers small-ship service
- •Dislikes large-scale entertainment
Recommended For You:
The Experienced Explorer
Luxury travelers who want destination immersion and access to smaller ports like Monemvasia.
You Enjoy:
- •Wants destination immersion
- •Interested in historical sites
- •Loves exploring small ports
Recommended For You:
What's Included vs. What's Not
Generally Included
- Ocean-view stateroom or suite accommodations
- All meals in all venues, including 24-hour room service
- Non-alcoholic beverages (sodas, specialty coffees, juices)
- Access to the Watersports Platform (kayaks, paddleboards) *when permitted*
- Onboard entertainment and destination briefings
- Signature beach BBQ and cultural events (on applicable sailings)
Generally Not Included
- Alcoholic beverages (unless a beverage package or All-Inclusive fare is purchased)
- Shore excursions (unless an All-Inclusive fare is purchased)
- Gratuities (unless an All-Inclusive fare is purchased)
- Wi-Fi (unless an All-Inclusive fare is purchased)
- Pre- and post-cruise hotel stays in Athens
- International airfare and airport transfers
Windstar offers an 'All-Inclusive' fare upgrade that bundles Wi-Fi, unlimited wine, beer, cocktails, and gratuities into the cruise fare for a more seamless experience.
Which Yacht Style is Best for You?
Wind Class Sailing Yachts
The Classic Sailing Yacht Experience
- ShipsWind Star, Wind Spirit, Wind Surf
- AtmosphereOpen teak decks and an intimate private-yacht atmosphere.
- SuitesOcean-view staterooms with a classic nautical feel.
- Ideal ForCouples, sailing enthusiasts, and travelers seeking an intimate sailing experience.
Star Class Motor Yachts
Contemporary All-Suite Yachts
- ShipsStar Legend
- AtmosphereLarge enough for additional amenities while remaining small enough for intimacy.
- SuitesSuite-focused luxury with more contemporary design.
- Ideal ForSuite-focused luxury travelers who prioritize space and amenities.
Compare The Details
Sailing Yachts
Ranges from 148 guests (Wind Star, Wind Spirit) to 342 guests (Wind Surf). A very small, remarkably personal social environment.
All-Suite Yachts
Approximately 312 guests. Offers a middle ground with more amenities.
Windstar Greek Islands Short
Explore the Greek Islands & Beyond
Discover iconic islands, hidden gems, and extraordinary ports accessible only to small ships.
Mykonos
Whitewashed buildings, blue-domed churches, windmills, and a glamorous atmosphere. Best for couples, shopping, and nightlife.
Santorini
Dramatic volcanic landscape and famous caldera views. Best for romance, scenery, and wine tasting.
Patmos
A quieter, more contemplative atmosphere associated strongly with Christian history and St. John.
Nafplio
Venetian architecture, cobblestone streets, and exceptional Greek cuisine. A sophisticated mainland experience.
Kusadasi (Ephesus)
The gateway to the extraordinary ancient city of Ephesus, providing a window into the ancient Roman world.
Monemvasia
A historic settlement beneath a dramatic rock formation with medieval architecture and a romantic atmosphere.
Angela Hughes Authority & Credentials
CEO, Trips & Ships Luxury Travel | Founder, Luxury Travel University
Angela Hughes
Angela Hughes has explored over 121 countries and spent more than four decades designing luxury travel experiences. She is widely recognized across the travel industry as a leading river cruise authority and active travel advocate.
"The best luxury vacation isn't necessarily the most expensive one. It's the one that fits the way you want to travel. That philosophy is especially important in Greece, where the difference between a large cruise experience, a small-yacht experience and a land-based island vacation can dramatically change the trip."
— Angela Hughes, On Active River CruisingKEY QUALIFICATIONS & ACHIEVEMENTS
- Over 4 Decades Designing Luxury Travel Experiences
- Explored 121+ Countries Across Seven Continents
- Recognized Industry Leader & River Cruise Specialist
- CEO & Founder of Trips & Ships Luxury Travel
- Specialist in Active River Cruising & Multi-Generational Travel
- Personal Relationships with AmaWaterways Executives & Staff
Don't Make
TheseMistakes.
Our luxury travel advisors reveal the most common pitfalls.
Assuming every Greek Island cruise is the same.
Windstar isn't simply a smaller version of a mainstream cruise ship. It is a different style of travel. The experience is centered around the destination, the intimacy of the yacht, personalized service, and relaxed luxury.
Rushing into Athens on embarkation day.
If your flight is delayed, your entire cruise can be affected. Arrive at least one or two nights before embarkation to recover from jet lag, explore the Acropolis, and enjoy a relaxed start.
Trying to do everything in Santorini.
Santorini can be crowded. Trying to see everything in a rushed day can turn an extraordinary destination into a stressful one. The better strategy is selective exploration—choose one primary focus like scenery, wine, history, or romance.
Frequently Asked Questions
Windstar offers small ships, a yacht atmosphere, and destination immersion. It's for travelers who prefer intimate lounges, personal service, and relaxed luxury over massive entertainment complexes.
For first-timers, the 7-night 'Treasures of the Greek Isles' is a classic. For repeat visitors or those wanting more cultural depth, longer itineraries combining Greece and Turkey are excellent.
Santorini is best for iconic romance, Mykonos for cosmopolitan romance, Patmos for a quiet atmosphere, and Monemvasia for historic romance.
The shoulder seasons of May through June, and September through October, offer excellent weather with fewer crowds. July and August are popular but hotter and much busier.
Yes. Because of their small size, Windstar yachts can dock in smaller, hidden-gem ports like Monemvasia, Nafplio, and Patmos, where massive cruise ships cannot go.
Windstar embraces 'Casual Elegance.' During the day, resort casual wear is appropriate. In the evenings, casual elegance is requested (no shorts, flip-flops, or t-shirts in dining venues), but there are no formal nights.
Non-alcoholic beverages, including specialty coffees, teas, and sodas, are included. Alcoholic beverages require purchasing a beverage package or booking an All-Inclusive fare.
Wind Star is a classic sailing yacht (148 guests) offering a romantic nautical experience. Star Legend is an all-suite motor yacht (312 guests) offering more spacious accommodations and contemporary amenities.
A 7-night cruise is standard, but you should plan for 10 to 14 days to include a highly recommended pre- or post-cruise stay in Athens to recover from jet lag and explore the Acropolis.
Yes! Windstar yachts feature a Watersports Platform. When the ship is anchored and local weather and regulations permit, you can swim, paddleboard, or kayak right from the back of the ship.
Santorini can be very crowded in peak summer. However, Windstar’s small group excursions and expert timing help mitigate this. Choosing a shoulder-season sailing also vastly improves the experience.
Not generally. Windstar is designed for adults. There are no kids' clubs, babysitting services, or children's entertainment onboard. The minimum sailing age is 8 years old.
Ready to Experience Greece by Yacht?
Let Trips & Ships Luxury Travel design your perfect Greek Islands journey.
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