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Windstar brings you closer to the world you’ve always wanted to explore. Their fleet of intimate yachts and iconic sail ships slip into ports the big ships can’t reach — places where authentic experiences await. Relish in connection and cultural immersion all along the Mediterranean coastline. Explore hidden harbors, charming seaside villages and iconic cities, all in boutique style thanks to Windstar’s intimate vessels. This is so much more than a journey — it’s the luxury of time, space and freedom.
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Rome, Italy
Seaside Dinner
Rome, Italy
Catania, Sicily
Wind Surf, Mallorca, Spain
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Cruise Beyond
Pair your local season getaway with the plush amenities provided by Cruise Beyond to savor every facet of your trip that much more.
Enjoy perks like:
- Up to $1,000 onboard credit per guest
- Complimentary pre-cruise hotel night and transfer to ship
- The Complimentary Beyond Inclusive Package, which includes Wi-Fi, select alcoholic beverages and gratuities
Introducing Local Season
Windstar’s winter Mediterranean sailings let you explore iconic cities with fewer tourists and more authenticity. Enjoy spacious attractions, vibrant local life and the rare opportunity to feel like a true insider.
Comfortable Weather
The Mediterranean is famous for its sunny, mild climate — even in winter. Enjoy forecasts perfect for strolling historic streets or enjoying a quiet seaside café.
Festive Atmosphere
Some of Europe’s legendary winter markets kick off as early as November. Many cities and countries have their own distinct winter celebrations.
New Ports and Overnight Stops
Windstar’s new winter itineraries are loaded with unique destinations not included in the summer months, like Naples, Catania, Genoa and more. Plus, they also feature overnight stays, so you can truly revel in the locale.
What’s Included in Your Windstar Cruise Fare
With only 148 to 342 guests per yacht, Windstar takes immense care to ensure every guest always feels welcomed and cared for. That’s why they include all the essentials for an unforgettable experience:
- Market Tours with Chef (Select Voyages)
- 24-Hour Room Service
- Locally Inspired Dishes
- Navigation Lessons – Visit the Ocean Bridge and meet the crew!
- Signature Onboard BBQ
- Enriching Lectures on history, culture and wildlife (Select Voyages)
- Nightly Port Talks
- Entertainment & Local Performances
- Unlimited Sodas & Bottled Water
- Specialty Tea & Coffee – Wake up with a cappuccino or English breakfast tea
- The Marina – Complimentary kayaks, paddleboards and floating islands (select voyages)
- Complimentary Yoga Classes
- Cooking Demonstrations
Featured Sailings
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Sorrento, Italy
24-Day Star Collector: Winter Mediterranean Adventure
Departs February 12, 2026, aboard Star Legend
Additional sailing dates available
Venice to Barcelona
This grand tour of the Mediterranean’s southern shores sees you sailing from the Adriatic to Gibraltar, soaking up serene locales every step of the way. Stroll seasonal markets dusted with snow in Croatia, try your hand at making pizza in Naples, trace the ghostly ruins of Pompeii and take advantage of milder weather throughout Spain.
Insider Highlight: In Spain, relish in the remnants of holiday sweets by eating your share of churros with chocolate and turron.
Barcelona, Spain
7-Day Southern Spain Winter Escapes
Departs February 27, 2026, aboard Star Legend
Additional sailing dates available
Roundtrip Barcelona
Walk in the shadows of Gaudi’s surreal creations, make authentic paella in an exclusive cooking class, sample regional wines and delicious tapas at scores of outdoor cafes and tour Picasso’s masterpieces. This itinerary delivers you the various gorgeous jewels of Spain’s southern coast in intimate style.
Insider Highlight: Everyone knows to check out La Sagrada Familia, but Colonia Guell is a lesser-known work of Gaudi well worth a visit.
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Dubrovnik, Croatia
14-Day Star Collector: A Winter Muse in the Mediterranean
Departs March 23, 2026, aboard Star Legend
Additional sailing dates available
Venice to Athens
Discover a poetic blend of history, cuisine and culture on this idyllic, extended itinerary through the Mediterranean. From the canals of Venice to the cradle of Western civilization in Athens, you’ll savor the slower pace of winter.
Insider Highlight: Oia in Santorini is renowned for its sunrises; set an alarm early enough to make it to a viewpoint as the start of the day ignites across the sky.
Athens, Greece
8-Day Winter in Italy and the Adriatic
Departs March 31, 2026, aboard Star Legend
Additional sailing dates available
Rome to Athens
For many, winter in Italy feels like a whole new country; plenty of elbow room at the most popular attractions is reason enough to visit — the locals being at their jolliest is just powdered sugar on the cannoli. With this itinerary, discover an even more relaxed side of the Mediterranean.
Insider Highlight: Herculaneum was also destroyed by the infamous Vesuvius eruption. But! This city is far better preserved than Pompeii, making for a surreal outing.
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Barcelona, Spain
7-Day Europe’s Winter Riviera
Departs January 15, 2027, aboard Star Explorer
Additional sailing dates available
Barcelona to Rome
This stretch of the Mediterranean is a fashionable haunt for reclusive celebrities, savvy travelers and in-the-know locals; your itinerary sees you joining an exclusive crowd. Overnights in Livorno and the Catalonian capital of Barcelona allow you to truly savor the scene.
Insider Highlight: Florence in the winter is a local affair — now’s your chance to see masterpieces like “The Birth of Venus” with (nearly) no crowds.
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