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Windstar Legendary Winter Mediterranean Season


7, 8, and 9 Day Voyages

Dec 2023 – Mar 2024

Starting at $1,399/pp*

* Price is per person. Solo travelers have no single supplement in select categories. Additional taxes and fees apply.

Explore the Mediterranean In A Whole New Light

See another side of the Mediterranean, away from the crowds of summer, for a more intimate exploration of the region filled with the magic of Christmas markets and the upcoming winter months beckons. Windstar Cruises new winter itineraries from December 2023 to March 2024, offer you the opportunity to discover iconic ports like Barcelona, Spain; Nice, France; Livorno (Florence/Pisa), Italy; and Rome in an entirely different light onboard the all-suite Star Legend, serving just 312 guests with accommodations starting at 277 square feet.

The Mediterranean in winter offers an exclusive perspective on these timeless destinations. Smaller crowds mean more personal interactions, while the weather cools down. Our overnight stays of these newly curated itineraries allow you to enjoy the cultural treasures, gourmet delights, and captivating history of Spain, France, and Italy with an intimate ambiance that’s simply unparalleled.

Winter in Rome allows you to see the Vatican, St. Peter’s Basilica, and iconic Roman landmarks like Piazza Venezia, Piazza Navona, Spanish Steps, and Trevi Fountain, all steeped in history and culture without the buzz of crowds. From Florence, head out to the Tuscan countryside to meet vintners at legendary vineyards; visit the Statue of David, the Academia, Ponte Vecchio, and the Opera House, immersing yourself in the artistic heritage of Italy. Spend the evening in Monaco rolling the dice with lady luck at the glitzy Grand Casino, stroll through the village of Menton with its huge belle-epoque palaces overlooking the sea, or go back in time with a chocolate and candied fruit workshop that been operating since 1820 in Old Town Nice. Gaudi’s Barcelona, the awe-inspiring Sagrada Familia, and the Gothic quarter allow you to dive into the world of art and architecture. Dine on tapas, take in a flamenco show, and sooth your senses with a rejuvenating dip in the thermal baths for a soul warming overnight in Spain.

Special Departures of Note:

  • During December, explore the charming Christmas markets throughout Europe offering delightful gifts and festive atmosphere to get you in the holiday spirit.
  • December 24, 2023: Spend Christmas in Rome with the departure.
  • December 31, 2023: Watch the spectacular fireworks in Barcelona for New Years and experience the tradition of the Three Kings Day and the folklore of La Befana.
  • December 10 – 31, 2023: experience the Green Line Festival/Light Festival for a unique visual spectacle.
  • January 28, 2024: witness the glamour of classic cars in the heart of Monaco at the Monaco Grand Prix Classic Car Exhibition.

With Windstar Cruises, we are redefining the concept of winter travel in Europe, making it a season of discovery and enchantment that is 180 degrees from ordinary. Join us on these exceptional journeys and experience the Mediterranean’s Winter Wonders. It’s time to embark on a voyage like no other, where the magic of the Mediterranean comes alive in its more intimate splendor.

Now is the best time to book your cruise with this special “Pick Your Perk” offer:

14 days or less

14 days or less
Free Upgrade to
All-Inclusive Fare
Extra night
onboard Star Legend*
Extra night
onboard Star Legend*
$200 per guest
Onboard Credir
$100 per Guest
Onboard Credit

* Premium Suites include Owner’s Suite, Classic Suite, and Deluxe Suite. Pre/Post stay will be onboard Star Legend and is not applicable for voyages that include Christmas or New Years. Terms and Conditions


Plus, Yacht Club Members receive double their Yacht Club Member discount for 10% off the Cruise Only fare for these sailings.


Transform your cruise into a private yacht style experience with everything you ever wanted. Make it an all-inclusive voyage for just $89 per guest per day with our All-Inclusive Fares and enjoy the ultimate in convenience and value with Wi-Fi, unlimited beer, wine, cocktails,
and gratuities or just purchase a la carte. It’s YOUR cruise and it’s your choice!

The fare is ideally suited for Windstar’s relaxing and highly personalized ambiance. Wherever you sail, this is the best and easiest way to bundle the most popular onboard amenities we offer. With the majority of your onboard amenities expenses taken care of upfront, spend your time enjoying uncrowded coastal destinations, award-winning cuisine, and authentic, off-the-beaten-path optional shore excursions in the cherished company of those you love most.


Wi-Fi allows guests to keep in touch with loved ones and share their vacation escapades while globe-trotting through Windstar’s signature small ports of call.

Unlimited Beverage Package

This ultimate beverage package includes all domestic and imported beer and 33 varieties of wine or sparkling wine by the glass plus cordials, liqueurs, aperitifs, cocktails, and mini-bar items. Cocktails are based on house and select brands, and guests may choose from more than 40 liquors such as Grey Goose, Hendricks, Johnny Walker Black, Ketel One, Glenfiddich, Hennessy, and more (brands rotate and are subject to availability.)

Hotel & Beverage Service Fee

All your hotel and beverage service fees are included with the purchase of the All-inclusive Fare. If you purchased beverages a la carte there is an 18% gratuity added to your purchase.

Itinerary at a Glance

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All Suite Ship

Star Legend is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach.

This all-suite yacht completed renovation as part of the  $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, elevated pool, and fitness area. The yacht also boasts all new bathrooms in every suite and a new category of Star suites, featuring a new layout. With ocean views and at least 277 square feet of suite comfort, Star Legend is the perfect yacht for cruising the Dardanelles and into scenic fjords from the serenity of your suite.

Carrying only 312 guests, Star Legend still tucks into small ports like Sinop and Honfleur or narrow waterways like the Corinth Canal. We can’t wait to welcome you on board for your next 180 degrees from ordinary adventure!

All Accommodations Feature

  • Queen Size Bed with Luxurious Linens
  • Interactive TV
  • Safe
  • L’Occitane Bath Amenities
  • Hair Dryers and 110/220 outlets
  • Mirrored closet with ample drawer space
  • Waffle Weave Robe and Slippers
  • Fully Stocked Mini Bar/Refrigerator
  • Direct Dial Phone
  • Fresh Fruit
  • Wi-Fi Internet Access(various plans available for purchase)
  • Granite vanity with magnifying mirror and chair

Your Windstar Voyage Includes

Our attentive staff will take care of everything you need and anticipate anything you dream.


(352) 575-9364