Europe in winter, reimagined: three Windstar cruises to book now

Windstar Cruises has earned a reputation for winter escapes to far-flung destinations like French Polynesia and the Caribbean. But this season, the small ship luxury line is expanding its repertoire, with winter journeys closer to home set to subvert expectations.

Responding to increasing demand from savvy travellers for year-round European sailings, Windstar has unveiled an impressive line-up of winter voyages in the Mediterranean and Canary Islands, paired with thoughtfully curated shore excursions.

Each voyage is designed to showcase the best of the local season, revealing new sides to familiar destinations. After all, what remains once the crowds of tourists have dispersed, and the heatwaves of July are a distant memory, is Europe at its most authentic.

Without further ado, here are three cruises, selected by World of Cruising, that show how Windstar is reimagining what a winter getaway looks like.

Winter in Italy & the Dalmatian Coast

Duration: Eight days

Ship:Star Legend

Dates: Multiple dates across 2025, 2026, 2027 and 2028. Sailings set to coincide with Carnival in Venice are likely to be the most sought-after.

Top ports: Rome, Naples, Messina (Taormina), Dubrovnik, Zadar and Venice.

Highlights: Along this voyage, you’ll have the chance to gaze at the Sistine Chapel, toss a coin in the Trevi Fountain, explore Pompeii and stroll the walls of Dubrovnik. Best of all, because it’s the local season, you’ll be able to do so at your leisure, without constantly jostling for space.

Venice is especially magical in winter, with a romance born of fog and silence. Mists swirl over the water, marble palazzi glow in the soft light and basilicas beckon on windy days.

The cold has its advantages, too. The ravenous mosquitoes have vanished, and crucially, so have the crowds. The latter means you have a fighting chance of securing a table at the restaurants most worth trying, just as traditional seafood is at its most seasonal. Think cuttlefish stewed in its ink or lagoon-fresh clams served with hearty polenta.

If your sailing coincides with Carnival, you’re in for a particularly memorable time. This is the season for masks, music and masquerade balls. The revelry begins with the Flight of the Angel: a young woman soaring by harness from St Mark’s bell tower to the Square below.

The Windstar difference: Windstar offers shore excursions that bring each destination to life. In Venice, that might be a canal tour where you can experience the city’s Gothic architecture at its most atmospheric or the chance to try your hand at the ancient art of mask making.

In Naples, you might explore the Royal Palace of Caserta, a baroque masterpiece that rivals Versailles. On a winter’s day in Rome, nothing warms the cockles like a pasta cooking class, complemented by wine pairings.

Southern Spain Winter Escapes

Duration: Seven days

Ship:Star Legend

Dates: A dozen different dates over the winter seasons of 2025, 2026, 2027 and 2028. Look out for the December 13th departure in 2025, which coincides with the Geminid meteor shower and allows you to explore local festivities.

Top ports: Málaga, Gibraltar, Cartagena, Valencia, Palma de Mallorca and Barcelona.

Highlights: On this local-season sailing, you’ll find there’s far more to the land of Cervantes than simply sun, sea and mile-long queues. Expect a season packed with cultural events, all celebrated with the spirit of beberse la vida (‘to drink life’) and quite literally toasted with sparkling glasses of cava and bright, herbaceous vermouths.

At Christmastime, you’re particularly spoiled for choice. The 18th-century Fira de Santa Llúcia in Barcelona is known for elaborate nativity scenes, which often feature the mischievous Caganer figurine. Festive illuminations light up landmarks throughout the city, including Gaudí’s dreamlike Casa Batlló.

Not to be outshone, Málaga similarly comes alive with dazzling lights. Calle Larios becomes a canvas for extravagant displays. La Concepción Historic Botanical Garden, which dates back to 1855, transforms into a winter wonderland, its paths and plants lit up for the season.

In January, celebrations continue with Epiphany, marked by grand Three Kings’ parades across Spain. In the Catalonian capital, Festa Major de Sant Antoni is another standout, with firework-brandishing devils and castellers (human towers) taking to the streets.

The Windstar difference: A major advantage of sailing with Windstar is that overnight stays are frequently built into itineraries, so you have more time to immerse yourself in a destination and experience it after dark.

On this sailing, Star Legend will dock overnight in both Barcelona and Málaga. These nights are set to be true scene-stealers, giving guests the chance to explore cities at their brightest and merriest.

Canary Island Idyll

Duration: 10 days

Ship:Wind Star

Dates: Multiple dates, from November 2025 through February 2026, including sailings that coincide with Christmas, New Year’s Eve and the Carnival of Santa Cruz de Tenerife.

Top ports: Santa Cruz de Tenerife, San Sebastian, Santa Cruz de Palma, Funchal, Lanzarote and Las Palmas.

Highlights: If you’re looking for winter sun, verdant landscapes and cultural riches, this voyage delivers on all fronts.

The weather in the Canaries and Madeira is some of the best you can find anywhere in Europe, with balmy daytime temperatures in the mid-teens to low 20s and ample sun – up to three times as much as parts of the UK.

Landscapes are at their most compelling, nourished by the winter rains. Madeira earns its reputation as the ‘Hawai’i of Europe’, with lush, undulating slopes you can explore by cable car or 4x4. Across the Canaries, you can expect winter flowers in full bloom, forming an entrancing contrast to the black sand beaches and lunar-like terrains of islands like Lanzarote.

Beyond offering glimpses of unique geography and flora, Windstar's winter sailings of these islands unveil their cultural treasures. While Venice may have the oldest carnival in the world, the Carnival of Santa Cruz de Tenerife is one of the biggest, outdone solely by Rio de Janeiro.

Meanwhile, for music lovers, the Canary Islands International Music Festival runs from January through February, filling concert halls across the archipelago with world-class orchestral performances.

The Windstar difference: One of the great pleasures of a Windstar sailing is feeling instantly at ease as you step aboard, thanks in large part to the warm, relaxed sociability you’ll find on the boutique, intimately sized ships. Whether you’re celebrating Christmas, Carnival or simply the sunshine, you’ll often find fellow guests happy to raise a glass and share discoveries after a day of exploring the islands.