I’m not a “Game of Thrones” fan, but my Dubrovnik tour guide told me to pose for a photo on the Jesuit Steps, site of Cersei’s famous “walk of shame.” I waited for one umbrella-twirling tourist to finish her own photo shoot, and then I had the steps to myself.
Let that sink in for a moment.
I was standing in a city famous for overtourism – one whose main streets are as packed with tourists in high season as they look during Cersei’s naked stroll through hostile throngs – and there was no one there.
It was at that moment that I truly understood why more and more cruise lines are offering winter itineraries in the Mediterranean.
They call it the quiet season, the local season, the cozy season, but let’s be real: It’s the off season. Most cruise ships abandon the Mediterranean in the late fall, repositioning to the Caribbean or possibly Alaska to escape grey, rainy days and chilly temperatures. Why grin and bear it when your assets are mobile and can chase the sun?
European lines like Costa Cruises and MSC Cruises have always kept some ships close to home during the winter, and Viking was another early adopter of winter Med sailings. But as European summers get hotter and travelers lean into travel trends that take them away from the crowds, more cruise lines are testing whether they can turn the off-season into a prolonged shoulder-season.
Windstar Cruises launched winter Mediterranean cruises on Star Legend in late 2023, and will launch its newest ship, Star Explorer, on that route in December 2026. MSC Cruises will do the same when its newest megaship, MSC World Asia, debuts with a season of seven-night Spain, France and Italy cruises that same month. Regent Seven Seas Cruises will sail its first full winter season in the Mediterranean in 2026, and sister brand Oceania Cruises will follow suit in 2027 with Oceania Allura.
But just because winter cruising is trendy doesn’t mean you’ll like it (which is exactly how I felt about the graphic “Game of Thrones”). I boarded Windstar’s Star Legend in early February for an eight-night cruise to Italy and Croatia, visiting hotspots like Naples, Sicily, Dubrovnik, and Venice to test whether the quiet and cozy season in Europe should become your client’s new favorite travel season or one to avoid.
TL;DR: it’s complicated.
No Crowds, No Sweat and the Price is Right
The best thing about cruising the Mediterranean in winter is the lack of crowds. Dubrovnik was empty. Taormina’s main drag was not overrun with tourists. My three-person tour saw only a single large group tour and a couple on their own during our visit to Croatia’s popular Plitvice Lakes National Park. Venice was happening because we arrived during Carnevale, but it never felt unbearable.
It wasn’t just the ports that were empty. Star Legend can carry 312 guests, but there weren’t even 170 passengers on my sailing. If Windstar didn’t upgrade your suite pre-cruise, you could negotiate for one on embarkation day with many rooms available. Dinner reservations were easy to schedule and then change; five of us showed up unannounced to new specialty restaurant Basil + Bamboo just for the burrata salad appetizer, and the maitre d’ didn’t bat an eye as he escorted us to a table in the empty-at-6 pm venue.
The second best thing about the quiet season in the Mediterranean is that prices are low. For example, Viking’s eight-day Barcelona-to-Rome itinerary starts at $2,799 per person, based on double occupancy, for a January 2027 sailing, but climbs to $5,799 for a September cruise, more than double the off-season cost. (I’m using Viking instead of Windstar for comparison purposes because it sails the same itinerary in winter and summer.)
And it’s not just cruise fares that are cheaper. Tickets to walk Dubrovnik’s Old City Walls are twice as expensive (40 vs. 20 euros) in the high season than in the winter. Entrance tickets to Plitvices Lakes National Park are also cheaper. Plus, with fewer visitors, it’s easier to get tickets, even at the last minute.
Coming to Europe after the snowstorm and record lows plaguing the U.S. East Coast, I was surprised how nice the weather was – despite the gloomy forecast ahead of my cruise. Most days were in the 50s and grey, but the rain was never a deterrent (except for embarkation day in Civitavecchia). Sicily was sunny, and I had shed at least two layers by the time my tour ended. Venice was a bit chillier and wetter, but still warmer than home. I met many couples on Star Legend from places like Madison, Wisconsin, and Alberta, Canada, who were thrilled to be away from the cold and snow.
Closures, Cancellations, and a Chance of Bad Weather
My Instagram feed erupted with Valentine’s Day photos of flooding in Venice’s Piazza San Marco, and snow was predicted for northern Croatia a few days after we left. Two weeks before my sailing, Sicily had been slammed by a destructive cyclone that destroyed coastal areas. Clients booking a winter Mediterranean cruise can luck out with mild temperatures – or they can arrive during a harrowing storm. It’s a risk.
Some winter cruise drawbacks are easily foreseen. I expected that grey skies and barren winter landscapes might not be as picturesque as spring’s blooms or fall’s colors. I also anticipated that outdoorsy attractions would be limited; adventure-seekers should consider if winter will offer the activities they desire.
What I hadn’t reckoned on was the number of closures winter brings to Mediterranean destinations.
My goal in Taormina was to eat cannoli and arrancini and browse the many stores that line the main drag, Corso Umberto. But my guide’s favorite cannoli bakery and a large percentage of the shops were closed for the season (as was the Four Seasons made famous by “The White Lotus” TV show). Dubrovnik on a Sunday in February was dead; I saw not a single open souvenir shop and only a few cafes serving the handful of tourists (mainly my shipmates and visitors from Eastern European countries escaping the cold).
Clients who travel to browse unique European shops and dine at renowned restaurants might be disappointed with the available options in the off season.
Small-ship cruise travelers are also especially hard hit in the off season. Star Legend was always the only ship in port on my sailing, and that meant group tours, either Windstar’s or third-party options, often got canceled due to lack of participants. Solo travelers taking advantage of discounted rates or waived single supplements should anticipate limited or no options for group transfers and might want to encourage new friends to join tours to ensure they meet the minimum participant number to run.
On the other hand, private tour guides are ecstatic to have work in the slow season and can be a great option for clients who aren’t excited about the cruise line’s excursion options. My Tours By Locals guide in Dubrovnik thanked me for getting her out of the house that day.
Ultimately, the pros outweighed the cons on my Windstar cruise, but advisors should make sure their clients set reasonable expectations when embarking on a winter cruise in the Mediterranean.
Uncrowded streets mean nothing if the attraction you flew all this way to see is closed or you have to manage the hassle of multiple tour cancellations. Explain the realities of winter in Europe to clients before they book, and they won’t be asking you to do the walk of shame upon their return.
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