The heat of the summer is the perfect time to start dreaming about a winter getaway. How about cruising the Mediterranean without all the crowds?
The problem with Mediterranean cruises has always been their availability. Most people cruise this region from June through September, and the majority of cruise lines only offer sailings April through November, redirecting their ships to the Caribbean during the winter months. That means that summer sailings often involve crowded ships, tourist-filled ports of call, overrun islands, and of course, hot, sweaty days.
But there are options for those who don’t need to travel during the busiest season of the year, and those options are growing. Historically, Celebrity, Costa, MSC, and Princess – all known for their large ships – have provided year-round itineraries in this area, with Viking dominating the market in small ship cruising. This year, Windstar Cruises entered the Mediterranean winter sailing arena with its Star Legend ship sailing the popular Rome ↔ Barcelona voyage.
Windstar’s debut created such high demand that they are adding five new itineraries, plus special holiday sailings, in 2025, with options to combine two trips for more in-depth exploration and experiences. One new itinerary, Winter Italy & the Dalmatian Coast sails from Rome to Venice and stops in Naples, Taormina, Dubrovnik, and Zadar. In a unique twist for shoppers, it is timed to correspond with Italy’s designated retail sales dates so passengers can load up on Murano glass, olive oil, and the famous Italian fashion.
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These unique itineraries are just one reason small ship cruising has become more popular in recent years. AAA Travel has reported that smaller ships are one of the biggest travel trends of 2024, and industry reports suggest that the growth of small ship popularity isn’t slowing down anytime soon.
What’s To Love About Small Ship Cruising
As someone who was a diehard big ship cruiser and took annual family trips on pretty much every cruise line out there, I have fantastic memories to look back on. But looking forward, I want something different, especially after experiencing my first small ship. Here’s why.
Small ships offer an intimate experience you just can’t get on large cruise ships.
Faces become familiar and you’ll find yourself striking up conversations and inviting others to join you for dinner. But it’s also your choice to never do that. You can eat whenever you like, with whomever you like, or sit alone and lose yourself in a book – no one dictates your seating time and how many people will be at your table. You won’t stand in lines, pick your way through crowds, or fight for a chair.
Service, dining, and cabins tend to be top-notch.
You’ll find all-balcony rooms or suites, quiet hallways, and easy access to common areas without worrying about which lounge is aft or which elevators are slow. Your cabin will be meticulously serviced, with special treats to surprise and delight you, and that level of service will extend to the entire ship’s staff, especially in the dining room. There, not only will you feel like you’re in a fine restaurant, but the food is more likely to be local, fresh, and customizable to your tastes and dietary restrictions.
And of course there’s the benefit of size.
Small ships have a big advantage when it comes to navigating narrow waterways, having the ability and permission to use certain ports, and offering excursions appropriate for 20 people versus 200. That means you’ll get to see what most don’t and really delve into the authenticity of a destination rather than be directed toward tourist traps.
What’s to Love About the Mediterranean in Winter
There’s a reason why these cruise lines have opted for year-round sailings in this region. Windstar President Christopher Prelog announced the line’s new itineraries this way: “Winter in the Mediterranean is a fantastic time to see a different side of this magical region, get to know the locals, and celebrate special holidays like Christmas in Florence, New Years in Dubrovnik, and Carnevale across Italy.”
It's the stuff of dreams, especially in the dead of summer when a national heat wave is making everyone a little grumpy. Booking a cool winter vacation now is enticing, and those dreams become even more attractive when you consider the additional benefits of a winter sail.
For one, airfare to Europe drops considerably in the winter months. It’s not unheard of to pay half the cost of flying to Europe during peak season. That’s money you can put back into your cruise experience or pocket for your next vacation.
You’ll also find different itinerary options during these months that better suit off-season travel, with opportunities to explore without the crowds, spend the night at various ports, and interact more with local communities. These cruise lines know that winter means you won’t be sunning in Cannes, so they go to extra lengths to make their excursions all the more interesting.
So if you’re ready to take the plunge into small ship cruising and shake up your normal winter routine, the Mediterranean is calling – now with more options than ever.
