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!).

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

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 is Lucca and Pisa, other fabulous medieval Tuscan towns 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

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.

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

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 serves 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

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.

And if anyone wonders, “Why, as a guest on a Windstar ship, which has amazing food, are you poking around food stalls,” you 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

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 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 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

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

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

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.

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.

If you go: 

• This quote from Rome-based Laura Itzkowitz, in her story about why cruising in the Mediterranean during winter is a special experience, first intrigued me to check out the possibilities: “Take it from me, an American living in Rome: Winter is the Mediterranean’s secret season.” Last winter, I added coastal Spain to my other “locals season” voyages from Rome to Barcelona and from Venice to Rome.
• Windstar continues to expand fall, winter and spring Mediterranean opportunities from now until 2028. You can visit Greece and the Amalfi coast, enjoy the extended explorations of a Star Collector: Spain and Canary Islands, or dive into Europe’s Winter Riviera, among others. 
• On a January visit to Venice, well after the festivities of Christmas and the new year, and before the annual celebration of Mardi Gras. I added a four day pre-cruise stay. What did I discover about Venice in “locals” season?

The post What It’s Like: Four Seasons of Splendor in the Mediterranean appeared first on Windstar Cruises Travel Blog.

I learned it was perhaps the place where the lost city of Atlantis had fallen into the sea and that Plato mentioned it in his writing, noting it had disappeared 9,000 years ago. I also knew that experts believed that Plato had added an extra zero — perhaps the first recorded typo. Nine hundred years ago, instead of 9,000, would have put the disappearance of Atlantis at exactly the time when an eruption created its massive crater and awe-inspiring cliffs.

Volcanoes are not something I am normally drawn to as I am to, say, a Caribbean beach or a Parisian café. And swimming in the crater of one wasn’t exactly on my bucket list. But I am drawn to adventure and to stories. As we were looking over the various excursions offered aboard Windstar’s “Treasures of the Greek Isles” cruise, “Sailing the Caldera” appealed to me.  The description — plunging into the green sulfur waters and a Greek lunch served on board — was alluring. The Atlantis mystery made me think that other stories like it would bubble up from the bottom of the caldera’s sea floor.

So on that June morning with a small clutch of like-minded passengers, we boarded our catamaran named the Odyssey (what else!). As we unmoored and began our gentle sail, our lovely guide, a young Greek woman named Vaso, explained to us what a caldera is. Basically it’s the crater of an extinct (or perhaps just dormant) volcano that is filled with water — in other words, an inactive volcano (one hopes). In Italy, part of the Bay of Naples is a caldera. We’d traveled there recently and learned about it, a miles-long fissure called Campi Flegrei that, were it to erupt, would ooze enough magma to fill 80 million Olympic-size swimming pools, according to one scientific report. The Campi Flegrei caldera has been in the news lately because of seismic activity — enough to keep residents in nearby towns on edge and with suitcases packed, and to have tourists cancel their Airbnbs. 

Back to Santorini! The caldera below the cliffs of Santorini were formed 3,600 years ago in 1600 B.C. when the volcano at the center of what was once a huge island erupted, essentially wiping out Minoan civilization. The Minoans had sailed to Santorini from Crete around 3000 B.C. and they vanished after the eruption. But, as Vaso told her rapt audience of 12, including two teenagers, it remains an archaeological mystery that no human remains were ever found at what is known as the ancient site of Akrotiri. Vaso’s story had me remembering Dr. Finkleman’s tales about Atlantis. Did the Akrotiri people leave long before or did they have some warning and were able to flee? It is possible that no one will ever know and in some sense the mystery only adds to its magnificent allure. 

We sailed the perimeter, with the massive cliffs of the caldera rising and encircling us, past Nea Kaimeni (New Burnt Island), one of the still smoldering volcanic cones of the caldera —in other words, inactive but not extinct, which is an important distinction. Here we stopped for a swim in the thermal springs around the nearby Palea Kaimeni (Old Burnt Island). We dropped anchor and those who wanted to do so jumped into the warm waters and floated around. That was what I’d signed up for and in I went.

The water strangely went from being very warm to cold, and other travelers and I joked about this. The underwater thermal springs bubble up, creating these warm patches, the equivalent of a Swedish shower that goes from hot to cold and back again.  The thermal springs are just a reminder that there is still activity down there.

I don’t know how long we swam. Even as I drifted, time drifted away. I lay, paddling on my back, looking up at the pure blue sky Dr. Finkleman told me about so long ago.

Back on board we were offered glasses of chilled Greek wine. There was white and rosé, a nice selection. Soon we were moving slowly along again. I was struck by the smoothness of our little sail, the sweetness of the day, and a gentleness I’ve rarely felt as if I were being cradled by the caldera.

About 20 minutes later we pulled into a cove where there was a house and a few makeshift structures along with two little boats. They were both bright yellow. One appeared to be a covered dinghy, perhaps used for ferrying back and forth from the mainland. The other was an elegantly appointed gondola with red trim and a white canopy, lovingly designed. “This is the home of Sostis,” Vaso told us. And then she told us Sostis’ sad story.

Years ago, Sostis met an Italian woman who was visiting Santorini. They fell in love and decided to marry, but after a time the woman returned to Italy. Bereft, Sostis moved to this cove where he remained all these years, awaiting her return. The yellow gondola with the red trim was the ship he built for her return. Sostis lived more or less as a hermit for many years until recently. When he turned 75 and became ill, he relocated to the mainland, which apparently his family had been begging him to do for years.  No one knows if he will ever return or what will become of his yellow boats.

Here we took another swim — though this time the waters were cooler with no warm water bubbling up. When we got back on board, lunch was served. We’d already been enjoying that Greek wine and it kept flowing as we dined on a spread of yogurt, tomatoes, a delicious Greek salad and chicken kebabs that were prepared on board. We each took our plates and perched ourselves either on deck or around the dining table in the shade. We went to the bow and joined a family of four who made room for us. The kebabs were juicy, the salad fresh, the wine cold and delicious.

Vaso had one more surprise for us before we docked at midday. We passed another inlet where there was a tiny church. “This,” she explained, “is the Church of the Seven Holy Young Men.” This church pays tribute to seven young Christian men who lived in Ephesus when the Romans conquered the area and required everyone to abandon Christianity and adopt the Roman gods as their religion. The seven young men refused and sought refuge in a cave where the Romans found them and sealed the cave, leaving the men to starve. Legend says that the men didn’t starve. Instead they slept for 200 years and only woke when Christianity was restored in the 19th century.

Then we made our way slowly back to the dock.  In truth I did not want this journey to end. If we had to sail all day — or as in the Odyssey, for 10 years — I’m not sure I would have objected. I could see how this place of mystery and beauty could evoke stories of unrequited love, heroes and martyrs. And I could envision Dr. Finkleman, who eventually retired to this place, reveling each morning in all this blue.

Editor’s Note: Mary Morris, an award-winning novelist and memorist and her husband Larry O’Connor, a writer and book editor, traveled aboard Windstar Cruises’ Wind Spirit to the Greek Isles. While traveling, they were inspired to write a series of pieces about the experience – both onboard and ashore; if you enjoyed this post, check out their other pieces: What It’s Like: Sailing the Greek Isles on Wind Spirit; Discovering Greece’s Peloponnese via Nafplio and Monemvasia; and In Greece, Putting Food First. And we have even more stories on a cruise around Greece.

The post Choose Your Adventure: In Santorini, the Wonderful Indulgence of Sailing the Caldera appeared first on Windstar Cruises Travel Blog.

“There’s a reason they call these islands Europe’s Hawaii,” Prelog tells me. “From black-sand beaches to cities with Spanish and Portuguese influences, it always felt to me like it was everything you could want in a vacation destination.”

Particularly if you make island-hopping easy.

The archipelago consists of Santa Cruz de Tenerife, its capital, and Las Palmas, Gran Canaria, Fuerteventura, Lanzarote, La Gomera and Ferro. Ironically, the islands are actually closer to the west coast of Africa than to Spain; Fuerteventura is just under 70 miles from Morocco’s Cape Juby.

Each one is distinctively different. Tenerife is lush with rainforests while parts of Lanzarote, with its dune fields and black sand beaches, feel like you’ve landed on the moon. La Gomera has a rugged mountain landscape. Santa Cruz de la Palma has a lively and colorful Caribbean vibe along with mountainous volcanoes and, like Lanzarote, thriving vineyards. Madeira, though not technically part of the Canary Islands, is often visited on itineraries in the region.

And here’s a fun fact: the Canary Islands are home to seven UNESCO Biosphere Reserve sites, so chosen for the purpose of conservation, research, education, and development of cultural and biodiversity in environmentally unique locations.

How to island-hop in the Canaries

The hot ticket right now is the 10-night Canary Island Idyll in autumn 2025/winter 2026 onboard Wind Star, the company’s 148-passenger sailing ship. The choice of Wind Star for this route was no accident, Prelog says. “Prevailing winds in the Canaries make a voyage onboard a sailing  yacht an extraordinary experience.”

Based from Tenerife, Wind Star calls at islands such as La Palma (Santa Cruz), Las Palmas (Grand Canary Island), La Gomera (San Sebastian) and Lanzarote, along with Madeira (Funchal), which belongs to Portugal. 

Getting to (and from) the homeport of Tenerife is easier than anticipated

The Canary Island Idyll itinerary home ports in Tenerife. I discovered the easiest flights from North America are on United Airlines, which now offers nonstop flights in both directions on select days between Newark (EWR) and Tenerife (TFS). If the nonstop schedule doesn’t work for you, there are daily one-stop flights from most major North American airports on American, Lufthansa, Swiss, and British Airways. There’s even an option to fly Icelandair with a Reykjavik stopover before ending in Tenerife. 

Check out our tips on what to do and see in the Canary Islands.

Santa Cruz de Tenerife

Tenerife is the largest, most populous and best-known of the Canary Islands, famous for its beaches, nightlife and the highest peak in Spain, Mount Tiede. Santa Cruz (meaning holy cross in Spanish) serves as the capital of the island and co-capital of the Canary Island archipelago. With a population of over 200,000, it is a bustling city, with an old town area that features colonial Spanish architecture, shops and eateries.

Best-known sights:

Whale and dolphin watching are popular shore excursions in Santa Cruz, but scenic drives rank highest for land-based exploration. Mount Teide dominates the skyline from almost anywhere on the island, and a visit to the Teide National Park gets you even closer to the volcano’s summit and its massive lava fields. There’s a cable car in the park to get an even better view.

For those who love markets, Our Lady of Africa Market, known as La Recova, features three multistory courtyards overflowing with food, wine, flowers and local goods.

Wonderful surprises:

Prelog admits that Tenerife was his second-favorite island in the Canaries (read on for his absolute fave), primarily because of the mountain scenery and hiking. While many of the 67 trails found in the Teide National Park are listed as difficult, one of the most scenic is Roques de Garcia. It’s about a 90-minute circuit trail, listed on most maps as easy to moderate, that lets you stretch your legs and feel like you’ve truly explored a bit of the island.

Bottom line:

Because Tenerife is often where you say hola or adios to the Canary Islands, spare time in port may be limited. It’s easy, though, to plan a pre- or post-cruise stay here. Windstar’s package incorporates a stay at the Iberostar Heritage Grand Mencey Hotel.

More info:

The Canary Islands Tourism website has a large section dedicated to all things Tenerife. Details about the Mount Teide cable car are at Volcano Teide.

Lanzarote

Lying just 78 miles from the coast of the African continent, Lanzarote is the third-most populous island and the fourth-largest of the Canaries. Its immense red and black volcanic landscapes give it an other-worldly feel. The capital city of Arrecife is home to only 64,000 residents.

Lanzarote is Prelog’s favorite island in the Canaries. When I asked him why, he was uncharacteristically at a loss for words. “It has a desert flair,” he finally said. “With the white buildings and the dunes, it’s very different. Variety is what makes the Canary Islands a perfect vacation, and with this itinerary, we can take you around to sample all the differences.”

Lanzarote is the first destination in the world to receive a Biosphere Responsible Tourism Certificate. That means it is not only good at protecting its uniqueness, it’s also developed a plan for sharing it responsibly.

Best-known sights:

You won’t find the lush green mountains and banana groves you will experience on Tenerife and Madeira. Lanzarote is stark. The landscape is what brings people here, mouths gaping as if they just landed on Mars. You can still enjoy beaches here, they come in both black and gold. Ride a camel in the dunes if you choose or simply take in the harsh beauty of it all.

Wonderful surprises:

As impossible as it seems, there are vineyards. Grape cultivars unique to the island are grown on the rocky lava fields close to the ground, much the same as you’ll find on Santorini. In fact, the visual similarities between Lanzarote and Santorini really suprised me (though the two islands really do feel quite distinct from one another).

And Lanzarote is not a huge cruise port. On some of Wind Star’s port days in Arrecife, it is the only cruise ship in port. On others, only one other ship is also docked.

Bottom line:

Lanzarote has a memorable desert beauty you won’t find on the other Canary Islands. Plus, there are things you can see and do here you won’t find elsewhere on cruises to many other regions in the world. Whether you aim to ride a camel, go four-wheel adventuring, or sit and sip volcanic wine, this is not a port of call you want to miss.

More info:

Look for details about Lanzarote on the Hello Canary Islands website.

San Sebastian de La Gomera

The island of La Gomera is the second-smallest, and one of the least-visited, of the Canary Islands. Its 142 square miles feature soaring volcanic mountains that provide the island with black sand beaches. The upper altitudes of the central island are dominated by the misty Garonjay National Park. The ship ports in the capital city of San Sebastion de la Gomera, with a population of just under 10,000. The city’s history is interwoven with the expeditions of Christopher Columbus.

Best-known sights:

Striking volcanic basalt formations, hiking and waterfall spotting in the national park (a UNESCO World Heritage Site), and the black sand beaches are the primary things to experience on La Gomera. San Sebastian Beach is the most popular near the port, with restaurants nearby. Most tours planned through the ship are of the sightseeing variety, a few with short walks in the national park. Choosing a short sightseeing tour leaves you free to explore a bit of the island on your own or venture to the beach for the rest of the day.

Wonderful surprises:

If you are looking for the perfect souvenir from La Gomera, shop for palm honey or guarapo. Another possibility is wine produced from the Forastera Gomera grape. History lovers can explore the Columbus House Museum, where Columbus stayed before setting out across the Atlantic, and the Torre del Conde and Church of Asuncion, both from the 15th century.

Bottom line:

San Sebastian appeals to nature lovers and those who enjoy dramatic scenery. It’s a highly walkable island, with more than 370 miles of trails and paths.

More info:

The La Gomera Canary Islands Tourist Information site has a wealth of information, including walking tours created specifically for cruise ship passengers.

Santa Cruz de La Palma

Santa Cruz serves as the capital and primary port city of the island of La Palma. It’s a relatively small city rich with Spanish history (we love the Plaza de Espana, anchored by the Iglesia Matriz de El Salvador). The Naval Museum (Museo Naval) has a replica of Columbus’ Santa Maria, and the cobblestone streets of the city’s historic center (walkable from the cruise port) are lined with examples of colonial Spanish architecture.

Best-known sights:

Can you ever tire of the black sand beaches? During winter, you can enjoy the warmth of the sand even when air temperatures are moderate. Water temperatures average in the low 70s, making it comfortable for a quick dip. The nearest beach to the cruise port is Bajamar. Also, La Palma is well known for its volcanic vineyards.

As with other islands, viewpoints or roadside lookouts are the best way to take in the island’s spectacular scenery, any driving tour should include several of the more prominent viewpoints. The island also has a wine-producing region near the caldera.

Wonderful surprises:

Tranquility is a word not often applied to tourist areas, but it sure does apply to La Palma and its multisensory experiences. One of the best places to find such tranquility is to venture north from Santa Cruz to Charco Azul, or Blue Pool. It is one of many pools in the Canaries that combine nature’s shoreline with a bit of human ingenuity to create a space where swimming in the sea is both safe and tranquil. It’s about a 40-minute taxi ride from the cruise terminal. The facility has changing rooms, showers and even a solarium.

Bottom line:

La Palma is an island with a slower pace, the kind of destination where you can wander a bit, maybe sip some local wine, and simply take in the beauty of the place. There are also plenty of tours for those who want to see the interior of the island and learn about the culture and history.

More info:

The Visit La Palma page on the Turismo de Islas Canarias website is filled with information about activities, trails, viewpoints for taking in scenery, and places of historical significance. The official tourism site of Spain also has an inspiring page on Santa Cruz.

Las Palmas de Gran Canaria

Las Palmas is the provincial capital, and the co-capital of the Canary Islands along with Santa Cruz de Tenerife. Population of the city is near 400,000 — almost half of the island’s population of over 800,000. The island is called the “little great continent” for the diversity of its landscapes, from beaches to pine forests.

Best-known sights:

Gran Canaria is known for its beaches and golf courses. The best beaches are in the touristy southern part of the island and are accessible via taxi. Las Canteras, however, is an urban beach not far from the cruise port in Las Palmas. Tours to the caldera and to one of several botanical gardens are also popular. Museum buffs have a handful to choose from, right in Las Palmas. El Museo Canaria provides a historical look at the island and its settlers.

Wonderful surprises:

The stunning Plaza Mayor de Santa Ana, dominated by the Cathedral of Las Palmas, is worth the cost of a hop-on, hop-off bus ticket. There are cathedrals in other cities in the Canaries, but this was the first church built in the islands after the Spanish invasion. Its architecture is a blend of Gothic, Neoclassical and Canarian — including pillars that mimic palm trees. The sand dunes on the island’s southern coast are a delightful surprise.

Bottom line:

Las Palmas is a large, busy city, with all the flair of any Spanish port. In addition to scenic landscapes, this populous island is known for archeological and historical treasures.

More info:

The Gran Canaria Tourism website and the Gran Canaria page on the Canary Island Tourism website both offer detailed information for visitors.

Madeira’s Funchal

Situated roughly 250 miles north of Spain’s Canary Islands, Madeira is an autonomous region of Portugal, comprised of four islands. The capital of Madeira is Funchal (on the island of Madeira). This energetic city hugs the coast and mountainside of Madeira’s highest peaks (Pico Ruivo reaches 6,106 feet above sea level).

Best-known sights:

One of the most unusual activities here is a toboggan ride. Picture sitting in a basket on wooden skids while two carreiros push and steer the wicker sled down a steep winding road between the villages of Monte and Livramento. The 10-minute speed ride is not for the faint of heart, but definitely fun to watch. There’s a cable car to Monte with a stunning view of the city and coastline a short walk from the port.

The cable car is also an option for visiting the Monte Palace Madeira Tropical Garden, a botanical garden located in Funchal, Madeira, but because the garden meanders down a very long slope, a better option is a taxi that drops you at the entrance then picks you up at the bottom exit two hours later. Don’t miss its oriental gardens, the Monte Museum for contemporary art, and the wildlife, such as flamingoes, that wanders throughout the property.

Wonderful surprises:

For a break from the city crowds, consider a visit to the charming fishing village of Camara de Lobos. The colorful village has small markets for shopping and charming cafes for a sip of Madeiran wine or a Portuguese beer. For a market closer to the port, the Mercado dos Lavradores is walking distance, and it is everything you’d expect to find in a European market — food, souvenirs, spices and local wine. The mercado is conveniently located next to the shopping area of Funchal’s old town, where you can also shop for shoes or sample some delicious gelato.

Bottom line:

Madeira is fast-paced and loaded with things to see and do. It has something for almost everyone who visits, and Prelog says that even a week in Madeira might not be enough to see it all. The best advice here is perhaps to squeeze in as much as you can, then be prepared to enjoy the beauty of the island from the deck during sailaway.

More info:

The Visit Madeira website has an incredible amount of information, including festival schedules and folklore as well as lists of monuments, churches and wineries.

If you Go: The Canary Islands

• Our Passport Guide is a great resource for facts and tips about a Canary Islands cruise. And if you want to travel it experientially, we love this wonderful trip chronicle. It really shows you what it’s like to be on this voyage.
• Canary Islands voyages, which have been hosted aboard Wind Star and will soon take place on Wind Spirit, her identical 148-passenger sister ship, are a perfect antidote to winter in the Northern Hemisphere. Itineraries run from mid-autumn to late winter.
• The 10-day Hidden Gems of the Canary Islands and Madeira is a great option for your first visit. And if you want a longer getaway, Windstar offers 18 and 20 day trips via Spain’s southern coast and Morocco.

The post Windstar’s Passport to the Canary Islands: Our Guide appeared first on Windstar Cruises Travel Blog.