Windstar Winter Mediterranean Cruise Deals

Explore the Mediterranean in a whole new light

Experience a different side of Europe with Windstar’s Winter Mediterranean cruises. Sailing from November through March, these voyages offer a rare opportunity to explore historic ports and coastal gems in peace, without the summer crowds. Expect mild weather, authentic local encounters and the relaxed, all-inclusive luxury that defines Windstar’s small-ship style.

Why cruise the Mediterranean in winter?

Winter brings a quieter, more atmospheric beauty to the Mediterranean. Explore ancient ruins and iconic landmarks at your own pace, enjoy seasonal celebrations like Venice’s Carnevale or Florence’s Christmas markets, and take advantage of lower airfares and added-value upgrades. On select sailings, Windstar’s all-inclusive promotion includes Wi-Fi, gratuities and unlimited beverages at no extra cost.

Boutique comfort aboard Star Legend

Your winter escape takes place aboard Star Legend, an elegant, all-suite yacht carrying just 312 guests. Enjoy the warmth of genuine hospitality, world-class dining and beautifully appointed suites with ocean views or private verandas. With five dining venues, including the acclaimed Cuadro 44 by Anthony Sasso, every meal becomes a celebration of Mediterranean flavours and seasonal ingredients.

Plan your winter voyage with our Windstar specialists

The Cruise Line is proud to partner with Windstar to bring these exclusive winter itineraries to our UK guests. Whether you’re drawn to Italy’s Adriatic coast, the Greek Islands or Spain’s sun-dappled shores, we’ll help you find the perfect sailing. Call our Voyage Consultants or browse our featured cruises below to begin your journey.