Windstar Greece Cruise: The Complete Luxury Greek Islands Guide

AN INTIMATE APPROACH

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.

QUICK ANSWER

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

FIND YOUR TRAVEL STYLE

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:

Wind StarTreasures of the Greek Isles

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:

Star LegendAthens to Istanbul

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

PORTS OF CALL

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.

✦ LUXURY TRAVEL EXPERTISE ✦

Angela Hughes Authority & Credentials

CEO, Trips & Ships Luxury Travel | Founder, Luxury Travel University

40+ YEARS EXPERTISE

Angela Hughes

Angela Hughes INSIGHTS & LEADERSHIPTrusted Greece Luxury Travel Authority

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 travel 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 Greece Planning

KEY 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

Direct consultation & VIP cruise amenities with Angela Hughes.Plan Your Trip

Expert Warning

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.