When Windstar announced last fall that it would be extending its Mediterranean season to year-round (from spring/summer/autumn), the first thing I wondered was this: How would a cruise in November–early March be different from one during the traditional April–October time frame? How would the new timings materially change the experience?

What I learned, after my recent cruise around the Mediterranean, was that it was equally enjoyable but different. How so? You definitely want to be prepared for the weather (I made the trip with just a carry-on and packed one of anything I could need, such as a sweater, a raincoat, a T-shirt and even a bathing suit). I spent more time in indoor spaces, like museums, restaurants, galleries, food markets and shops, and made some fabulous discoveries that I’d missed on other cruises in the Mediterranean where I’d been more interested in beaches, outdoor cafés and hiking trails. On our visits to Rome, Florence, Nice and Barcelona, the atmosphere was vibrant; we encountered plenty of other travelers but rarely ever a crowd (also rare: other cruise ships!).

Take it from me, an American living in Rome: Winter is the Mediterranean’s secret season.”

Laura Itzkowitz, Conde Nast Traveler

And one key change for cruising at this time of the year is that the itineraries are different. During the Mediterranean spring/summer/fall seasons, the ships tend to call at smaller, more out of the way villages and towns that are basically just open during the mainstream travel season. This time, we spent our time in cities that bustle all year long.

Our weather was mostly quite temperate, yet I do encourage anyone considering a winter cruise to remember that you’ll want to be a bit flexible and a bit adventurous when planning your touring. Some of us onboard even spent time swimming in Star Legend’s pool! And the hot tubs definitely were a boon.

What’s it like to sail around the Mediterranean in winter? Read on.

Coming home

Windstar’s Star Legend

As always, arriving at a Windstar cruise is comforting because, for veterans, you’ll undoubtedly run into amazing crew and staff with whom you’ve already traveled. And if you’re new, it doesn’t take long to warm into the embrace. 

Star Legend overnights tonight in Civitavecchia, which as many cruise travelers know (and yet if you’re new-to-cruise, no worries) is about a 1½ hour drive from Rome itself. Rome, like Florence, somewhat unusually for Italy, is a bit far inland to be a true port city. I love that we have an overnight here — and a full day tomorrow — if only because I didn’t have the free time to travel to Rome for a few extra days pre-cruise.

Our trip, should you want to follow along, begins here, moves on to Livorno for Florence (a somewhat similar situation in which Florence itself is inland, as are Lucca and Pisa, another fabulous medieval Tuscan town that you can access there). After that, the exploration schedule eases a bit. We head to Nice, Marseille and finally Barcelona. We have overnights as well in Nice and Barcelona. And there are no scheduled sea days. It’s going to be a busy cruise.

This trip means so much to me. I have visited all of these amazing cities more than a few times but have not been back since the pandemic. So I can’t wait to share visits to places I’ve loved, and unveil new discoveries, both.

Just a bit of background: I’m a big fan of “relax and absorb.” When we all first visit Rome, the sightseeing list includes the Colosseum, Vatican, Pantheon and Trevi Fountain. In Florence you can’t miss the Duomo, and museums like the Uffizi and the Academia. And yet on this trip, I’ve encountered a lot of travelers who have already been to many Mediterranean hotspots. The appeal of this voyage is the more relaxed time of year.

In Rome, I explore favorite, familiar niches and make a new discovery

Rome’s charming neighborhood around the elegant Piazza Farnese/Carolyn Spencer Brown

There were nine of us on the bus bound for the shore excursion “Rome on your own” and I was struck by the fact that everyone onboard had been to Rome before and had very specific ideas on what they were going to do in our destination city. (The other tour offered today was a Vatican-intense experience).

Going to Rome without a plan, whether it’s your first time or multi-time visit, is as crazy as spending a day in Tokyo or Stockholm or Paris. You need a plan. I’ve been to Rome so many times, even had a marriage proposal there, and yet — it’s still overwhelming and there are distances to be covered.

You should allow for time to get lost.

My plan was to revisit neighborhoods that I’ve loved in the past, like the Piazza Navona, Campo De Fiori and Palazzo Farnese, all pretty tightly bunched together in the shadow of the Tiber. I wanted to have a relaxing lunch of Rome’s famed carbonara pasta with a smidge of red wine, and then wander over to the Piazza ‎di Spagna (the Spanish Steps, which is both touristic and utterly fabulous).

Even with some time lost wandering in circles (my memory wasn’t as good as I’d hoped), a few restless moments cursing Google Maps for telling me to go northeast or southwest instead of left or right, and a bonkers recommendation that the best market in town was the seriously touristy one at Campo De Fiori (boy, has that piazza changed since my first visit, when as a callow and poor young traveler, I rented a room at a convent on the square), still, it was a great day. There was a great lunch at a restaurant a block behind Piazza Navona, a café I chose because the strongest scent of garlic wafted out its front door.

Lunching on Rome’s traditional carbonara pasta near Piazza Navona/Carolyn Spencer Brown

My favorite moment — as happens on all great days even if you do plan ahead — was a totally unexpected one, at Rinescenti, Italy’s sort-of fancy department store. This one had been written up by the uber-stylish Wallpaper design magazine, and the thing that intrigued me was its rooftop terrace. It was part of a rather pretentious food hall (selling fancy groceries like 36-euro olive oil flasks for which no info on its value was provided) but wow, the outdoor, rooftop deck offered the most amazing views above the city. You could breathe, rest, reboot, and watch a spectacular storm heading west to east, from the Atlantic to the city itself. And, ironically, on this first week of March, the sun shining on us was really warm (I peeled off a layer of clothes but then layered back up when I got outside, on the street level).

It was nice to meet up with our bus mates for a no-stress trip back to the ship (and a PS, the motorcoach had outlets for charging your devices; just make sure to bring an adapter).

Some of our fellow travelers took the train back and forth, and I’ve done that in the past, but opted for the convenience of the “on your own” option and was glad I did. Once we were back onboard, our captain announced that our sail-away would be delayed because a passenger was caught up in a train delay. I thought it was wonderful that the ship waited — but I wouldn’t want to take that chance.

Tonight we sail from Civitavecchia, north to Livorno, which is our gateway to Florence.

Onboard, it feels like we’re traveling in a cocoon

Cozy Cuadro 44 is one of my favorite restaurants on all Windstar yachts/Carolyn Spencer Brown

Star Legend is largely identical to Windstar’s Star Pride and Star Breeze. If you’ve traveled in any of these yachts, you’ll immediately feel at home once you walk up the gangway. I love that I know where my favorite haunts are, that the Yacht Club, the all-day-long coffee bar and deli also serve fresh squeezed orange juice in the morning. There’s the secret hot tub, all the way forward, on deck 5, which you’ll often have all to yourself.

The standard accommodations are all roomy suites, with either picture windows or Juliet balconies, and have the same layout (save for whether the bed is positioned by the window and living room by the door or vice versa). All have the walk-in closet, more movies programmed onto the television network than you’ll have =time to watch, and super comfortable beds with a nautically inspired seating area by the window or the entrance.

Perhaps my favorite moment so far on this trip occurred on our first night, docked at Civitavecchia. I had an early reservation at Cuadro 44, the cozy Spanish restaurant helmed by Michelin-starred chef Anthony Sasso. It’s become one of my favorite restaurants anywhere at sea; the menu is inventive, the crew and staff make you feel so warmly welcome, and the food is just delicious. This time, I discovered a new dish, the fideos mar y montana (toasted angel hair pasta, confit chicken, chorizo and clams) that joins the lamb chops and churros with chocolate sauce in my own personal “Cuadro Hall of Fame.”

So, on this night, the sun had just set, and I was surprised to see, from inside the cozy restaurant, tucked perfectly at a table along the wall, a flash of light. There was a spectacular show going on outside — a humdinger of a thunder and lightning storm with the rain coming down so hard it was blowing sideways. I may have been the only guest at that point in Cuadro 44 but I was by no means alone — the crew and staff joined me to watch the storm. It ended as abruptly as it began.

In Florence, the culinary arts, 20th century fashion and ancient artifacts

Here’s a great overview of Florence we visited on a toilet stop!/Carolyn Spencer Brown

Today, on our second port call on this Mediterranean-all-year-long cruise on Windstar’s Star Legend, could potentially feel a bit like “Groundhog Day” after yesterday’s visit to Rome from Civitavecchia. As excited as I am to be in Italy for the first time since the pandemic, both of these towns are, as mentioned yesterday, some distance inland (luckily, other ports to come, including Nice, Marseille and Barcelona, are within walking distance of the ship).

There was, on this call at Livorno, an option to sign up for a Florence “on your own” excursion, but it was such a new opportunity from Windstar (not listed pre-cruise as a shore ex option on Windstar’s website, for instance) that I was the only one to sign up. I ended up taking the regular Florence tour, the one that visits the Accademia Galleria to see Michelangelo’s statue of David. I figured I’d revisit the masterpiece and then arrange to meet the tour at the end. And in fact, I wasn’t alone there — several other travelers booked on the shore ex were return visitors to Florence and wanted to do their own thing, too. So, I think there’s potential for more offerings for experienced travelers.

The drive from Livorno to Florence was beautiful as we passed through Chianti country before heading up to a lookout point for an absolutely gorgeous toilet-stop (when was the last time you got those four words together in a sentence?).

Bottom line: Florence is, according to Lucia, our guide (and I believe her), one of the most historic of Italy’s many old cities. And if in my mind, visiting Italy’s famous cities now, as opposed to high season’s summer, would be a cakewalk, well, let’s just say that there may not be many cruise ships in the region, but tourists won’t feel lonely, at least in early March.

There’s definitely a great energy around Florence (a lot of school kids, a sprinkling of Asian visitors, independent Americans) but I do wonder if Florence is becoming the “new Venice,” in the sense of rather overpowering crowds around the Uffizi and the Accademia, and then sprawling beyond, that really transform your experience. One huge plus: If you’re on this tour, your guide gets the tickets in advance. Huge advantage.

And, like Rome, if you’re exploring Florence independently, you will want to plan your day, to make sure you get to see everything on your list. On this trip I wanted to explore the city’s Central Market. The ground floor, even during a rather fallow time of year when there’s not so much freshly grown produce (still no asparagus yet, just a bit early) though plenty of seafood, was, as it’s always, fascinating to see what people are buying.

Florence’s Central Market sells the usual foodstuffs and lots of ready made dishes, too/Carolyn Spencer Brown

And if anyone wonders, “Why, as a guest on a Windstar ship, which has amazing food, are you poking around food stalls,” they will understand when they see all the counters of ready-made dishes (and plenty of cafés, too). On this market’s second floor, it was even better than a food court, with all manner of treats, from chicken roasting right in front of you to decadent pastries, wines and beyond. There was even a cute gift shop that sold kitchen and gourmet packaged food (the requisite 36-euro bottles of olive oil were there aplenty). I kept thinking, in my family, where we all have different tastes, Central Market is a great lunch stop: There’s something for everyone.

Another new discovery in Firenze

Florence’s Gucci Garden celebrates the design house’s fashion in a contemporary way/Carolyn Spencer Brown

Another first in this port, which I had visited before, was a trip to the recently remodeled Gucci Garden. Mind you, I’ve never been particularly intrigued by the Florence-based Gucci’s fashion house, but after my morning in the Accademia, I wanted to experience the city’s more recent culture too. Gucci Garden is an elegant complex incorporating the Gucci Osteria, a boutique and bookstore, and a series of multimedia and visually colorful exhibits. What I loved about the experience was mostly its gallery, where you could ogle themed rooms (one on Gucci’s signature loafers through the decades, another with hundreds of handbags, a third that showcased gowns and tuxes as worn by a blend of celebrities throughout different decades). It definitely transported me into a different period of time and reminded me that Florence has more to offer than ancient artifacts.

My last stop — I packed a lot into the five hours I had to explore — was to head across the Ponte Vecchio, admiring the jewelry, to the other side of the Arno River. Here, on an easy stroll, you’ll find the Boboli Gardens and the Pitti Palace, and while it definitely was a gorgeous late winter day to embrace its flora and fauna, I just opted to explore the neighborhood of Santo Spirito. It’s an artistic area that feels both steeped in time and absorbed in the present. And there’s nothing like a soul-satisfying local meal in Il Santo Bevitore, a restaurant that was so focused on locals there wasn’t even a menu in English to cap off an adventurous day.

Two days in Nice, one of the Mediterranean’s most famous winter getaways

Nice’s old port, with Star Legend docked just behind/Carolyn Spencer Brown

Nice itself is a welcoming cultural city with amazing vistas over its old port and the Promenade des Anglais. Much of its draw has to do with its scalloped harbor and beachfront (even now, people were sunbathing though I didn’t see anyone sea bathing), and for its magnetic appeal for artists like Henri Matisse and Marc Chagall, both of whom are honored with museums. The farmers market in the old city, lined with restaurants and cafés, is a great place to people-watch and eat traditional Niçoise cooking.

Everything was open. One day I took the train to Monte Carlo to meet friends for lunch at an Italian café on the waterside. On our second day, it was all about rather leisurely exploring of Nice itself, walking from our ship in the old port, around the lovely seaside park that rings Castle Hill. The market in the old city was bustling (a good spot for lunch was Jenny’s Café, right across from the flower-seller). I spent an hour in the Musée de la Photographie, just behind the market, which I learned about from this story on culture in the Mediterranean’s winter; it hosts rotating exhibits. On this visit, I was completely absorbed by “The Manhattan Darkroom,” showcasing the work of Henri Dauman, a Frenchman who ultimately chronicled the lives of celebrities in the 1950s and 1960s. Going back in time there reminded me of my visit to the Gucci Garden in Florence, when you just step out of your life for a bit and come back refreshed.

What’s head-spinning about our visit, even with two full days and an overnight, is how many villages and towns there are to explore and, thanks to a fantastic train system (which, from our ship’s dock in the old port, had a station that was quite walkable). Some of us headed out for Monte Carlo (and in fact Windstar offered a “Monte Carlo on your own” tour on our overnight for those who wanted to dress up and gamble at its famous casino). Eze, the medieval town on top of a rock, fronted the sea between Nice and Monte Carlo, and so did the charming beachfront village of Villefranche-sur-Mer. St. Paul de Vence, a medieval village in the foothills of the Alps, is another option; it, like Nice, has long been a magnet for art and artists. 

Midway through our cruise, here’s what I’ve learned

A winter sunset admired from the deck 5 forward whirlpool in Nice/Carolyn Spencer Brown

A couple of thoughts re traveling in the Mediterranean (we can’t even call it the “off” season anymore, just year-round), based on learnings on this wonderful trip.

1. Weather is never a guarantee on any cruise, anywhere. The best you can do is pack accordingly to whichever season you’re in (so far, I’ve got most of the right pieces — a couple of T-shirts, leggings, one sweater, one easily foldable raincoat, a dress for dinner with a couple of takes-no-room silky tops, and one pair of evening shoes). I’ll admit that the Dansko leather pair that’s been my primary footwear is killing my feet. I broke down today in Nice and bought a nice pair of Birkenstocks. They’re like butter — though I have to figure where in my carry-on the flesh-stubborn Danskos will go.

2. We’ve had variable weather but on the whole it’s been quite comfortable, 50s and up, and sunny. Our two days in Nice absolutely lived up to expectations. I think my face is sunburned. And yet tomorrow, just down the Riviera, Marseille is getting a huge storm and we’re skipping that port and going straight to Barcelona, so you never know.

3. I have loved this itinerary and its overnights, particularly in Nice and (anticipating) Barcelona, where the ship docks right in town. In Nice, you can spend one day poking around the city — and another trying to decide between forays to Eze or Monte Carlo or St. Paul de Vence. And for do-it-yourselfers, the public transport is so easy!

4. So far, there’s not as much ship time as I normally like on Windstar (I love the ships) because the ports are so interesting! A rainy day could change that, and you could pivot to the spa, and a nice long lunch, and a comfy day watching movies in bed. Just saying …

A change in plans

In early March, a lovely lazy alfresco lunch on Star Legend on the way to Barcelona/Carolyn Spencer Brown

After Nice, we were scheduled to call at Marseille, a wonderful city that celebrates its nautical heritage. As we were sailing out of Nice, Capt. Mark Symonds informs us that we’re going to skip that port and head straight to Barcelona. Obviously, there was disappointment, but Windstar’s tradition of having captains offer detailed explanations of how decisions are made (complete with persuasive visuals) is such a great touch. By the end of his quite thorough presentation, we all were nodding heads in agreement.

Instead of Marseille, we had half a sea day (which was a real pleasure on this otherwise very port-intensive voyage), and I hightailed it to the spa for a massage and some time in the relaxation room. Oddly enough, since the storm wasn’t all that far from us, skies were sunny, and the sea was calm. And travelers did what they do on a nice day at sea — solving puzzles in the Yacht Club, swimming and sunbathing by the pool, taking restorative naps.

We didn’t have as much “free” time as we anticipated, alas.

Cruises always seem to start off nice and slow, then finish way too fast

An unexpected afternoon in Barcelona’s Port Vell, a lovely waterfront neighborhood just steps from our ship/Carolyn Spencer Brown

When you think about a cruise around the Mediterranean, at any time of the year, weather is always a factor in how you spend your day. On this voyage, the first season of winter cruises that Windstar has offered, we’ve had great luck: Almost every day has been picture-perfect. And yet I’d argue that it’s how you pivot based on atmospheric influences (laughing) that makes a travel experience a wonderful one. In fact, those of us on Star Legend this week finally got our come-uppance.

When we docked, right in town, Barcelona was sunny and warm but here we could see traces of the weather en route to Marseille; scudding clouds were moving away and the pavements were damp.

I’ve been in Barcelona so many times and one thing I have never done, and have wanted to, was to ride the Montjuic aerial tram. This afternoon would have been perfect, but I got busy and it didn’t happen, and I’m thinking, tomorrow, Saturday, our last full day onboard, is another opportunity.

Making a Pivot

Belly up to the bar at Barcelona’s Boqueria and have a fresh snack/Carolyn Spencer Brown

And yet, Saturday, at dawn, it rained so hard it blew sideways. Not a great day for Montjuic, for sure. There were two options: an onboard day, reading, relaxing, watching movies, playing puzzles in the Yacht Club, and perhaps another foray to the spa. Or: bundling up, as I was prepared to do, and diving into Barcelona’s famous Mercado, its Boqueria, its food market. I’ve been before, on fleeting visits. This time, I wandered around leisurely and absorbed the market more fully than I might have done on a sunny day.

For sure, it’s a touristic market. I would recommend that you start off by taking a lap around the food stalls and then hitching up on a bar stool at one of the handful of cafés that offer freshly prepared seafood and nice pours of whatever you drink (coffee machines were busy, so too were pours of San Miguel beers and simple Spanish wines). The people around you will likely be Americans (at least on this day, even in early March) and the rain is beating down so hard on the Boqueria’s metal roof that the whole place thrums, and it’s cozy and warm and delicious to be here.

Here, I met Tim, from Charleston, South Carolina, whose platters of shrimp and sardines and his glass of rose were his “good night” snacks (he’d partied all night and was heading back to his hotel). I opted for a breakfast of fried calamari, in which the cook plucked the fresh squid just in front of me and threw it into the fryer. The people-watching was so much fun.

And then I went shopping. You can buy fabulous souvenirs (salts and oils to take home and I didn’t spot any of the ridiculous 36-euro carafes of olive oil that were all over Rome and Tuscany), and also wonderful pastries (see photo, in which one baker, working below the market, created delicious sweets. The lemon pie was the best ever). Just follow your nose, garlic in one direction, sugar in another.

These days, I love to bring back gifts like unusual olive oils, teas, and other foodstuffs/Carolyn Spencer Brown

Afterward, missing Star Legend and knowing I’m leaving tomorrow morning, I headed back to the ship for a late lunch. It felt like I was coming home. In my so-comfortable suite, I started organizing my belongings, packing a bag. I hated to think about leaving. I just didn’t want this trip to end and wished I’d planned for a back-to-back that would take me around the Mediterranean back to Rome. Feeling indulgent, I ordered room service lunch (great burger, the first of the trip), switched on the television, and began watching “Roman Holiday,” with Audrey Hepburn and Gregory Peck.

It was the best possible pivot on a rainy day.

Editor’s Note: Windstar will continue to sail in the Mediterranean year-round. In winter 2024/2025 it’s offering four different Mediterranean itineraries, with additional calls in Venice, Athens, Naples and Genoa. Itinerary options include Barcelona to Rome, Rome to Venice and the Dalmatian Coast, and a Venice to Athens route.