Windstar Cruises Details Its Unique 2025-26 Winter Mediterranean Season

Windstar Cruises has announced details and opened for bookings its unique 2025-2026 winter Mediterranean sailing schedule.

windstar cruises star legend exterior

As one of the few cruise lines to sail in the Mediterranean in the winter, Windstar Cruises is leaning into the growing trend of off-season travel.

Today, the small-ship line has announced its 2025-2026 winter Mediterranean schedule, including six unique itineraries plus six Star Collectors, or voyages that combine itineraries for more in-depth exploration. These competitively-priced Star Collector sailings (which include free laundry service) invite guests to stay longer and experience even more of Europe.

windstar cruises star legend exterior
Star Legend (Photo courtesy of Windstar Cruises)

Along with the opening of new sailings, Windstar Cruises is pairing an Early Booking Offer which includes a $200 onboard credit per cabin plus a free upgrade to All-Inclusive Fares. That means that wifi, gratuities, and unlimited beer, wine, and cocktails are provided at no additional cost. This offer expires on October 31, 2025.

“Winter in the Mediterranean is a fantastic time to see a different side of this magical region, get to know the locals, and celebrate special holidays like Christmas in Florence, New Years in Dubrovnik, and Carnevale across Italy,” said Windstar’s President Christopher Prelog. “Sailing year-round in the Mediterranean has been very successful for Windstar, so much so that we are now expanding our winter offerings due to its popularity.”

valetta malta windstar cruises
Valetta, Malta (Photo courtesy of Windstar Cruises)

Windstar’s winter sailings highlight ports that it doesn’t normally visit in the summer like Valencia, Spain; Crotone, Italy; and Catania in Sicily. The 2025-2026 season also debuts a brand-new port for the line: Genoa, Italy. There, guests can visit the most important maritime museum in the Mediterranean, experience the biggest aquarium in Europe, or wander the Palazzi dei Rolli — a group of stunning palaces from the late 16th and early 17th centuries.

The season will also include overnights in Dubrovnik, Venice, Nice, Barcelona, Malaga, and Livorno (Florence) making long days of exploration possible, as well as late drinks and dinners while in town.

All of these 2025-2026 winter Mediterranean cruises will take place aboard the 312-guest Star Legend, which has a minimum of 277 square feet accommodations.

The vessel features five dining veues: Amphora, Veranda, Candles, Star Grill by Stephen Raichlen, and Cuadro 44 by Anthony Sasso. Chefs continue to shop for fresh seafood, produce, and local specialty items to bring the flavors of the destination on board even during the winter months.

cuadro 44 windstar cruises dining restaurant star breeze
Cuadro 44 on Star Breeze (Photo courtesy of Windstar Cruises)

Additionally, sailing just after the harvest is a plus for wine tours when winemakers have more time for personalized attention amidst the cellar season. Passengers also have the chance to enjoy treats from the region’s Christmas markets during this time of year.

These winter Windstar Cruises sailings will depart from Athens, Barcelona, Malaga, Rome, and Venice from November 2025 through March 2026.


Have you ever taken a cruise in the Mediterranean in the winter before? Would you consider booking one of these newly-opened itineraries? Drop us an anchor below and let us know!

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Sarah has been writing about the cruise industry since 2015, and in that time has taken a dozen cruises and counting. Her favorite onboard activities include trying the casual dining options, spending time in the spa’s thermal suite, and attending the love & marriage show. You can keep up with her on Instagram at @IAmSarahJaneB.
Sarah Bretz, Contributor
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