Ports Unknown: Windstar Cruises’ “Mystery Cruise” Injects Surprise and Adventure Into Cruising | Lifestyle Media Group

A palpable buzz builds as a crowd gathers on the open-air decks of Windstar Cruises’ Star Legend, eagerly awaiting a big announcement. We’ve just set sail from Athens, Greece, on the cruise line’s first “President’s Mystery Cruise,” an eight-day voyage so secretive that even the cruise line’s own president on board has no idea where we’re headed. After much playful teasing and build-up, the captain ceremoniously opens an envelope to reveal the long-awaited news. “Our first port, with fantastic weather and rich, ancient culture,” he announces into the microphone, “is in Italy and it’s … Taranto!” The crowd erupts in cheers and applause, some even embracing strangers in shared excitement.

Italy wasn’t exactly on my cruise bingo card, and I had to immediately pull up a map to figure out where Taranto was — I’d never even heard of it. For months leading up to the mystery voyage, set to depart and return to Athens, Greece, I imagined myself sailing to white-washed Greek islands or exotic Turkey. I had even strategized with fellow cruisers, using AI tools and online sleuthing to decipher the vague clues we were given before departure. As an uber-planner who always battles FOMO, going with the flow was not easy for me, and I had to let go of any preconceived expectations, including the desirable Greek islands. 

What we did know is that the ports would stay true to Windstar’s ethos of going to off-the-beaten-path and smaller locales. The inspiration for the mystery cruise took root during a 2024 sailing in Tahiti, when unexpected cyclones forced a detour to the remote Marquesas Islands. Guests repeatedly commented that each day felt like a “mystery” — and the idea stuck. From that serendipitous experience, Windstar began shaping a first-of-its-kind itinerary designed to reignite a spirit of adventure, especially for their devoted cruise base (about 80-percent of the cruisers on my ship had previously sailed with Windstar). “In today’s world everything is planned, this cruise is the opposite,” Christopher Prelog, president of Windstar, tells me during the sailing. “This is where we challenge the norm. This cruise is not meant for the masses. If you want to go to the Greek Isles, we have a beautiful program there, and it’s breathtaking. This cruise is meant to surprise and excite you.” 

A sheet with clues about our next destination awaited us in our cabin each day, with the mystery ports revealed 36 hours before arrival. After each announcement, I’d scramble to change or stay with prebooked shore excursions that were previously listed with vague descriptions, from culturally enriching cooking classes to wine tastings and visits to historical sites. At our first stop in Taranto, a coastal port in Puglia located at the heel of boot-shaped Italy and an inaugural port for Windstar, I zipped off on an excursion to Alberobello, where it felt like I’d been dropped into a fairytale gnome village. The UNESCO site boasts the highest and most preserved collection of trulli, whitewashed huts with conical or domed roofs that date back to the 14^th century. Rumor has it that the homes were cunningly crafted of dry stone so they could be quickly dismantled when tax inspectors came around, then later rebuilt. 

Another day, we arrived at a bucket-list port for me: Sicily’s Naxos Giardini, near Taormina, which is now tourist-famous thanks to the Max hit show The White Lotus. Our tour bus inched up winding roads to reach Taormina, dramatically perched on rocky cliffs that survey the deep-blue Ionian Sea and Mount Etna blanketed in a cloudy mist. After exploring the town’s grand dame — the ancient Greek Theatre, which offers a glimpse into the town’s Greek origins — I spent hours wandering the old streets of Taormina, gawking at its tapestry of historical landmarks and stopping at several cafes for arancini, pizza and pasta. The smell of citrus wafts through the air, and lemons super-charge almost every product sold there, from culinary treats to clothing. 

But the most treasured port of call for me was Reggio Calabria, where the town of Scilla romanced me with its mystical tales of sea monsters and charming historic district dotted with fishing boats and houses built on the water’s edge. It’s another storybook spot that begs leisurely strolls through the cobblestone streets, past shops and narrow alleyways where cats lazily nap on doorsteps. I dropped in stores to pick up Calabrian chili oils for souvenirs and refreshed with a bergamot granita (Italian ice) by the sea. By this third port, the idea of going somewhere completely unplanned had suddenly settled into my soul, and I was embracing the spontaneity and unknown. 

Our last port was unspoiled Kalamata, Greece, a gastronomic paradise located in the southern Peloponnese, which immediately stunned with its stark contrast of green mountains and turquoise waters. I skipped a formal tour and instead dug into the local food scene, perusing their weekend farmers’ market to sample meaty purple olives and scoop up aromatic herbs grown in the mountains. I also sought out a tiny family-owned restaurant in the historic district to indulge in a souvlaki pita topped with yogurt that I still dream about today. Pointing to Windstar’s ability to take their smaller ships go where the big boats can’t, we never saw another ship at any of our ports.

The cruise line also prides itself on being the “anti” mega-cruise experience, with a laidback, fun-loving spirit. No stuffy ball gowns and suits are needed for dress-up nights, and cruisers can eat where and when they want during dining hours and with whom they want. The Star Legend is an all-suite ship, with luxuries for people like me who cherish indulgences such as a walk-in closet, a bathtub, and an ample sitting room with a sofa and chairs. With just over 300 people onboard, it was easy to find a spare sun lounger on the deck and the ship never felt crowded. The bubbling hot tub connected to the glassy pool is a popular spot to sip an Aperol spritz (or three — it’s vacation, after all). 

The Star Legend’s dining options were better than many cruise ships than I’ve previously sailed on. There are numerous onboard dining options, including Amphora, the main dining room that impresses with glittering chandeliers, white cloth-draped tables and an elevated dinner menu that touts signature dishes created in partnership with the James Beard Foundation. My personal favorite is Candles, a romantic, glassy restaurant nestled on the back of the ship that wows with its views, particularly at sunset, and a high-brow menu centered around premium cuts of meat. But honestly, I enjoyed the evenings when I was still in my swimsuit and coverup, casually posted on a couch on the deck to enjoy the buffet options. 

While a mystery cruise is certainly not for everyone, most of the people on the inaugural cruise were already excited to the book the 2026 Mystery Cruise that begins and ends in San Juan, Puerto Rico. As proof that spontaneous travel is trending, Windstar reports the 2026 cruise was nearly sold out the week it was released. For me, the trip was a gentle reminder that travel doesn’t always need to be structured, and some of the most rewarding experiences came from exploring unexpected destinations I might never have chosen on my own. Would I do it again? Absolutely. But first, I have a meticulously planned Greek Islands adventure calling my name — color-coded itinerary and all. Windstar’s next Mystery Cruise departs on March 20, 2026, aboard the 224-guest Star Seeker, Windstar’s newest yacht, based in San Juan, Puerto Rico. Visit windstarcruises.com.