Star Legend

12 Impressive Mediterrenean Cruise Itineraries To Consider – For A Uniquely Crowd-Free Vacation

When Windstar Cruises had to unexpectedly relocate its freshly-renovated Star Legend ship last fall due to unrest in the Middle East, the beloved luxury cruise brand unexpectedly launched a popular new success: winter cruises in the heart of the Mediterranean. For travelers looking for a way to avoid the oversized tourist crowds in Europe’s most popular destinations this summer, winter itineraries coupled with Windstar’s intimate, small ship sizes, are a guaranteed way to feel like you have the best of Europe to yourself.

Windstar’s first winter Mediterranean season was so popular that even more itineraries are in the works for this upcoming winter season. Take a look at some of Windstar’s most enticing Mediterranean cruise itineraries to choose from, whether you want to travel this winter or beyond.

Europe’s Winter Riviera

Image Credit: Windstar Cruises.

The cornerstone of Windstar Cruises’ winter in the Mediterranean cruise itineraries is the 8-day Europe’s Winter Riviera journey, taking passengers to some of the most impressive destinations in Italy, France, and Spain with sailings from Barcelona to Rome, or vice versa. Numerous late 2024 and early 2025 departure dates mean travelers will have plenty of opportunity to enjoy highlights like overnights in Barcelona, Spain and Nice, France as well excursions to tiny towns in Tuscany, like Lucca, Pisa, and San Gimiano, before arriving in Rome.

Southern Spain Winter Escape

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Starting this December, Windstar’s Southern Spain Winter Escape will be a memorable way to enjoy some of Spain’s most charming and historic cities. This 8-day cruise sails roundtrip from Rome, with stops in cities like Cartagena, Valencia, and Málaga along the way. An extraordinary New Year’s sailing includes an overnight in Palma de Mallorca, one of the most vibrant places in Europe to ring in the new year.

Treasures of Southern Spain and Morocco

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Or, opt for a slightly different itinerary along the coast of Spain with the 10-day Treasures of Southern Spain and Morocco experience. Late fall and mid-spring departures from Lisbon, Portugal, head to Tangiers, Morocco, and then head up the golden coast of Spain to destinations like Málaga, Cartagena, and the island of Mallorca. Alternative routes start in Barcelona and trace the same route before culminating in Lisbon.

Winter in Italy and the Adriatic

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You’ll love the 9-day Winter in Italy and the Adriatic cruise from Windstar that departs from Athens, Greece and arrives in Rome, Italy. Explore historically rich destinations in Greece like Delphi, enjoy an overnight on the island of Corfu, and relish in stops at hidden gem ports in the “heel” of the boot of Italy before heading on to Catania in Sicily and then to Rome. This unique itinerary is currently only available with a departure date of November 6th, so make sure to book soon to secure your spot on the recently renovated luxury Star Legend.

Winter in Italy and the Dalmatian Coast

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With departure dates in November, January, and March, the 9-day Winter in Italy and the Dalmatian Coast sail that embarks in Rome and culminates in Venice, or vice versa, is sure to be one of the favorites of this winter cruise season in the Mediterranean. Highlights include an overnight in the historic walled city of Dubrovnik, Croatia, and a stop at Zadar before an overnight in the breathtaking port of Venice.

Winter in Croatia and Greece

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Windstar’s Winter in Croatia and Greece itinerary takes passengers to four different countries over the course of just 9 days. Departing from Venice, Italy, and tracing an intriguing route down the Adriatic Sea, this itinerary includes a stop in Koper, Slovenia, before visiting Zadar and the walled city of Dubrovnik in Croatia, Kotor in Montenegro, and fascinating destinations in Greece like Delphi and the Corinth Canal. Windstar is currently only offering this exclusive itinerary for a March 25th departure from Venice, so make sure to book ahead if you want to enjoy what’s sure to be the Mediterranean cruise experience of a lifetime.

Rome and Prix du Monde of Monaco

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This is one cruise itinerary you won’t find anywhere else. Windstar’s Rome and Prix du Monde of Monaco, now an annual tradition, brings passengers right to the port of Monte Carlo for the world-famous Monaco Grand Prix. It’s the highlight of an impressive sail that departs from Barcelona, Spain, and visits tiny, tucked-away ports like Palamos, Spain and Cannes and Sanary-sur-Mer in France before ending the 8-day experience in historic Rome.

Yachtsman’s Harbors of the Rivieras

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One of the benefits of sailing on Windstar Cruises’ small-sized luxury vessels is the ability to access under-the-radar ports that larger vessels could never visit. If this sounds like precisely the off-the-beaten-path experience you’re looking for, then the Yachtsman’s Harbors of the Rivieras itinerary is for you.This 8-day cruise conveniently starts in Barcelona and ends in Rome, but visits beloved, laidback ports like Palamos, Spain, Portofino, Italy, and Sanary-sur-Mer, France along its route.

Adriatic Archipelagos and Greek Goddesses

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Travel between Athens and Venice on Windstar’s Adriatic Archipelagos and Greek Goddesses itinerary. Currently only offered during the summer, this itinerary has highlights that include visiting four countries in just one trip – Italy, Croatia, Montenegro, and Greece. Highlights include an overnight in Kotor, Montenegro, considered a hidden gem in the Adriatic, and visits to lesser-visited destinations in Greece like Katakolon and Monemvasia.

Treasures of the Greek Isles

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The eight-day Treasures of the Greek Isles itinerary is one of Windstar’s most popular cruise itineraries in the Mediterranean, offering round-trip travel from Athens to some of the country’s most beloved destinations. Multiple sailings throughout the year offer guests plenty of travel options on a journey that visits spots like Mykonos, Patmos, and Santorini, as well as lesser-visited Greek ports like Nafplio and Monemvasia and the Turkish port of Kusadasi as the gateway to the famed ruins of Ephesus.

Sicilian Splendors

palma de mallorca
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Offered in May, July, and September of next year, the Sicilian Splendors itinerary is an impressive 11-day journey to smaller, lesser-visited Sicilian ports you’ll immediately fall in love with. Look forward to visiting destinations like Lipari, Catania, Gozo, Porto Empedocle, and Trapani. The cruise also includes a stop at the historic capital of Valletta on the island of Malta, as well as stops at the ports of Sorrento and Amalfi for a rich experience in some of the most picturesque spots along Italy’s Amalfi Coast.

Windstar Special Cruises | Wine Cruise: Sicilian Splendors

Star Legend
Image Credit: Windstar Cruises.

In addition to its standard cruise itineraries, Windstar also offers a series of specialty experiences focusing on food, wines, and so much more. If this is what you’re after, try a cruise itinerary like the Wine Cruise: Silician Splendors, offered this September. It charts the same enticing route as the standard Sicilian Splendors sailings but offers enrichment seminars with wine tastings and much more along the way. Another popular specialty cruise is the annual President’s Mystery Cruise; the 2025 iteration will depart on April 19th, 2025 on an 8-day roundtrip voyage from Athens to an unknown array of the most spectacular destinations in the region.

carley rojas avila

Carley Rojas Avila is a bilingual New York-based travel writer, editor, content marketer, and the founder of the digital travel publications Explorers Away and Home to Havana. Carley is an expert on all things Latin America, the Caribbean, and Cuba, having lived and worked in four different countries in the region. Her writing has appeared on the Associated Press wires and in Travel + Leisure, Yahoo, MSN, Euronews, The Weather Channel, and more. When she's not writing about her travels, find her front row at a Bad Bunny concert, befriending street cats, and taste-testing every pizza in Havana.