Roundtrip from Athens aboard Wind Surf
This itinerary is one of those “greatest hits” sailings—but done in a way that feels more immersive and less rushed thanks to the small-ship experience. You’re blending iconic islands, ancient history, and plenty of time to actually enjoy each place instead of just checking a box.
You’ll start in Athens, where 3,000 years of history come to life at the Acropolis and throughout the city. From there, the pace shifts into island time. (Opt for the pre-tour to spend more time in the Greek mainland!)
In Mykonos, expect those postcard-perfect white buildings, blue accents, and waterfront cafés. You can keep it relaxed wandering town—or dive deeper with a visit to Delos, one of Greece’s most important archaeological sites and the mythological birthplace of Apollo.
Kusadasi is your gateway to Ephesus, one of the best-preserved ancient cities in the world. Walking its marble streets really gives you a sense of what life looked like thousands of years ago. That evening is a standout—Windstar hosts an exclusive dinner and concert right in the ruins, which is the kind of experience most travelers never get.
In Patmos, things feel quieter and more spiritual. You can visit the Cave of the Apocalypse and the hilltop monastery tied to St. John, or simply soak in the scenery and slower pace.
Then comes Santorini—arguably the most dramatic arrival of the trip. Think cliffside villages, sweeping caldera views, and those iconic blue domes in Oia. Options here range from wine tastings to exploring the ancient site of Akrotiri.
Throughout the sailing, excursions let you tailor the experience—whether that’s a hands-on cooking class in Mykonos, private touring, or wine-focused experiences. And because it’s a smaller ship, you get closer to the destinations and avoid the crowds that come with larger cruise lines.
Why this itinerary works so well:
- A really balanced mix of history, scenery, and culture
- Iconic destinations without feeling overly packed
- Unique experiences like the private Ephesus evening event
- Flexibility to explore independently or with curated excursions
- More intimate, relaxed onboard atmosphere
It’s a great fit for travelers who want the highlights of Greece—but with a little more depth and a lot less hustle.
As part of Windstar's Wind Class, the 342-guest Wind Surf offers a sailing experience like no other — one with real working sails.
Wind Surf features common areas that include the lounge, the pool deck and bar, the Yacht Club Café, a wine room and much more.
This flagship sailing yacht features stylish staterooms and multiple suites, including opulent Bridge Suites, an Officer’s Suite, and brand-new versions of the Broadmoor and Sea Island Suites
Every inch of your Ocean View 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). Bathrooms feature L’Occitane en Provence bath toiletries.
Most category staterooms are 188 square feet, with several larger suites available. All cabins are ocean view, no inside rooms.
Note: The Wind Surf does not have balcony staterooms. All rooms and bathrooms are scheduled for a makeover in late 2026.
Cruise Prices begin at $3649 per person, double occupancy, inclusive all meals (all restaurants), snacks, drinks, gratuities and taxes. Single occupancy rates begin at $5956.
Our group also receives a $100 per person shipboard credit which can be used towards excursions of your choice.
Also included: An after-hours "Evening in Ephesus" event exclusive to Windstar guests. Enjoy a 5-course, white-glove-service dinner under the stars accompanied by a trio from the Aegean Chamber Orchestra among the ruins.
Why not see more of Greece and extend your stay?
Begin your trip a few days early with a fabulous land extension in Greece. Delve into the ancient wonders of early Western Civilization, featuring Delphi, Castalian Spring, the Grand Temple of Apollo, Delphi Museum, Meteora, the Acropolis, and the Parthenon
Package includes 3 hotel stays – 2 nights in Athens, 1 Night in Meteora at premium hotels, transportation, breakfast daily, lunch at Delphi and Meteora, Expert Guides, & Entrance fees. *Package is subject to availability
Pricing:
$1900 per person for double occupancy
$2400 for single occupancy
Dining on the Wind Surf is relaxed and varied, with everything included and no rigid schedules.
Amphora serves as the main restaurant with rotating, globally inspired menus, while Stella Bistro offers a more refined, French-inspired option. Candles is a guest favorite for open-air steak and seafood dinners under the stars.
During the day, Veranda offers casual breakfast and lunch, and the Yacht Club Café keeps things easy with coffee and light bites.
A highlight of the week is the signature deck barbecue—fun, social, and set right under the open sky.
Shore excursions ore designed to feel immersive rather than rushed, with a wide range of options in every port—typically anywhere from a handful to a dozen or more choices depending on the destination.
These experiences lean heavily into authentic, local experiences, so you’re not just sightseeing—you’re connecting with the culture. Think guided walks through ancient sites like, visits to monasteries and historic landmarks in Patmos, or exploring iconic villages and wineries in Santorini.
There’s also a lot of flexibility in style, from history-focused tours with expert guides, food and wine experiences, active options like hiking, or easygoing cultural visits and free exploration.
Text or Call Lucy : 410-774-6060