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Windstar's New Winter Cruises Through the Mediterranean Are Designed for Curious Travelers

Alessandro Moggi

“We could combine this with a trip to Leonardo da Vinci's birthplace,” suggests Paola Donato, a shore excursion expert in Italy for Windstar Cruises. It's a January morning, and I'm standing on the tree-lined grounds of the 16th-century Villa Dianella winery in Tuscany with Donato, project manager Melissa Witsoe, and destination manager Gonzalo Mones as they choose locations for new shore excursions for their Legendary Winter in the Mediterranean sailing. This year marks the first time Windstar will sail the Med in the colder months, but the trio is already planning for 2025.

Being in the region in the offseason represents a contingency plan for Windstar. The line was planning to launch its first itinerary in the Middle East, but when hostilities between Hamas and Israel broke out, it had to seek other options in places with more stability. Within three weeks, it had put together a framework to introduce new itineraries in the Mediterranean.

Winter in Europe's summer playground might seem like a hard sell, but it suits the times we're living in. As the high-season crowds and heat waves become increasingly overwhelming and the so-called shoulder seasons of spring and fall get busier, winter is the one period when you can reliably escape the hordes of travelers. “You can engage with locals in a more authentic way as they go about their daily lives,” Witsoe adds, “fostering genuine connections.”

Built as a hunting lodge for the Medicis, Villa Dianella sits in the countryside on the outskirts of Vinci, where Leonardo was born. We'd come here because ships will dock in the Tuscan port of Livorno for two full days, and Witsoe was seeking places for wine tastings, lunches and dinners, and overnight stays. We stroll through the village of Montecarlo di Lucca and visit two other wineries before sitting down for a truffle-filled lunch served by the third-generation owner of Savitar Tartufi in San Miniato. Villa Dianella is the penultimate stop of the day. Positioned on a hill with views of the rolling countryside, a vegetable garden, a historic wine cellar, and recently renovated rooms in the former stables, the property is undeniably enchanting. The problem: Its rooms are closed until Easter.

Seasonal closures are one of the biggest challenges of cruising the Mediterranean in winter. Windstar tried to skirt the issue by skipping smaller ports, like Portofino and Amalfi, that they would normally call at in the spring and summer and focusing instead on all-season destinations like Rome, Florence, Nice, Marseilles, and Barcelona. This also allows them to safely dock their ships at port instead of anchoring offshore, where strong winds and currents can pose a threat. Though their first sailings were less than half full, they had positive feedback and an influx of bookings for rest of the winter. Next season, they plan to offer four wintertime itineraries, with stops in cities like Naples, Genoa, Venice, and Athens. Shore excursions will forgo outdoor activities like cycling, but some guests will likely find that walking tours of cities like Florence, Nice, and Barcelona are more pleasant when they're not sweating under the summer sun. Take it from me, an American living in Rome: Winter is the Mediterranean's secret season.

Windstar Cruises

Established in: 1984

Areas of operation: 4 continents, 300 ports

Wow factor: Excursions include helicopters to Icelandic glaciers for snowmobiling.

Known for: Immersive sails in French Polynesia, where they have sailed longer than any other line.

This article appeared in the April 2024 issue of Condé Nast Traveler. Subscribe to the magazine here.

Originally Appeared on Condé Nast Traveler