The first clue appeared on my cabin door a few hours after I boarded Windstar Cruises’ 312-passenger Star Legend in Athens. “Our first port of call on this Mystery Cruise is also an inaugural call for Windstar Cruises. Nestled by the Ionian Sea, this ancient city boasts a bridge that swings, a castle that stands guard, and a history that dates back to the Spartans,” the clue read. I started to envision the destinations that touch the Ionian Sea, but the hints were vague enough that I couldn’t pinpoint a specific place.
Later that evening, everyone gathered on the main deck for a warm welcome by Windstar’s president, Christopher Prelog, and the ship’s captain, Pedro Pinto, who finally revealed where we would be heading after a full day at sea. “The port after tomorrow [has] fantastic weather, a very rich ancient culture, a beautiful place with sunny days, is in Italy . . . and it’s called Taranto.” Cheers erupted among the passengers.
We plan our lives to the tee and sometimes our planning gets in the way ... the mystery cruise should take all of that away and celebrate the spontaneous part of being human.
It may seem crazy to board a cruise without knowing where you’re going, but that’s exactly what I—and 300 other passengers—did. Windstar Cruises’ inaugural President’s Mystery Cruise was inspired by a 2024 cruise to French Polynesia that had to be rerouted to the Marquesas Islands at the last minute to avoid three cyclones in the ship’s path. As the original itinerary was scrapped and the captain charted a new course, passengers began to say they felt as if they were on a mystery cruise—and they loved it.
On that cruise, “somebody said, ‘This cruise is completely different than advertised, and it’s the best thing you’ve ever done. You should do more of it,’” Prelog told me aboard the ship.
Charting the surprise course
After Taranto, the next (surprise) port was Taormina, Italy.
Photo by Federico DiDio Photography/Unsplash
When the second clue arrived, I took a look at the shore excursions on offer and immediately had a strong feeling about where we were headed next. Our second port of call would give us access to an ancient Greco-Roman theater, a village with cinematic ties, vineyards 800 meters above sea level, and the largest mountain of its kind in Europe. As a six-year resident of Rome and an avid lover of Sicily, I knew we were headed to either Taormina or Siracusa. On the assumption that it would be the former, I immediately headed to the destination services desk and booked the “Twin Jewels of the Legendary Coast” excursion, which included a visit to the aforementioned Greco-Roman theater, a stunning archaeological site overlooking the sea that I’d wanted to see ever since I’d missed it on my first visit to Taormina in 2021.
A couple of months before the cruise, passengers were given a list of shore excursions kept intentionally obscure, and they were invited to book them in advance. The clues appeared on our cabin doors two days before we arrived in each port, and passengers were invited to submit their guesses to reception by 5 p.m. to be entered into a raffle to win a prize. The following day, the mystery port was revealed, and destination manager Felipe Menezes gave a talk to provide more details about the location and the shore excursions available. Passengers then had a chance to book, change, or cancel the excursions they signed up for in advance. I booked four shore excursions in advance, but when the ports were revealed, I changed two of them and canceled the other two so I could explore on my own.
I initially had some doubts about the third port. A clue alluded to an archipelago named for the master of winds, but it was replaced a few hours later by a new clue mentioning ancient bronze warriors and a distinctive culinary heritage featuring a spicy spreadable sausage. I later learned that because the Corinth Canal—a narrow waterway that allows ships to pass between the Ionian and the Aegean seas—was unexpectedly closed on day one, some of the following ports had to change. But because it was a mystery cruise, the average passenger likely didn’t even realize.
Reggio Calabria was another stop on Windstar’s new mystery cruise.
Sean Pavone/Shutterstock
The third port of call was also a new port for Windstar: Reggio Calabria, the largest city in Calabria, the region that forms the toe of Italy’s boot. When we docked that morning, I joined a group of about 20 passengers for a shore excursion to the charming seaside village of Scilla and a visit to the Museo Archeologico Nazionale di Reggio Calabria to see the Riace bronzes, a pair of miraculously intact fifth century B.C. sculptures discovered in the sea off Calabria’s coast in 1972.
Following another sea day, our final port of call was Kalamata, on Greece’s Peloponnese coast. Like many other passengers aboard the ship, I had guessed that because we were departing from Athens, we would likely be sailing around the Greek islands and maybe Türkiye. In a way, though, the mystery cruise was still a Greek cruise of sorts: every port of call in Italy was once part of Magna Graecia, ancient Greek colonies on the Italian peninsula. At every port, we learned something about the destination’s Greek history. I also appreciated that we stopped at small, off-the-beaten-path ports instead of the usual suspects, like Venice and Naples.
“This was an area that was really unvisited by cruise ships, and we really wanted to highlight the mystery component,” Melissa Witsoe, Windstar’s product manager, explained during the sailing. It’s all part of the brand’s larger mission to help bring guests to lesser-visited ports that are off the tourist trail and could benefit from tourism. And while Windstar still goes to some of the Mediterranean’s overcrowded cruise ports, the company is promoting offseason travel as a way to experience those destinations without the masses.
The final stop on Windstar’s mystery cruise was Kalamata on Greece’s Peloponnese coast.
Vangelis T/Shutterstock
The growing mystery cruises trend
It turns out mystery cruises are a growing trend. U.K.-based Fred. Olsen Cruises has two mystery cruises scheduled for this year and one for next year, sailing from various ports in England. Greek family-run Variety Cruises will operate a weeklong mystery cruise in June, hosted by the company’s CEO, and it will depart from Malta and end in Naples. River cruise company Uniworld is offering a seven-night mystery leg as part of its 50-night Rivers of the World cruise next year.
“I’m not a person that easily gives up control, but it was kind of easy because I knew that no matter what they provided, it would be up to their regular standards, if not higher,” Joy Weinbaum, a passenger aboard the Star Legend, told me during our sailing. She and her husband, William, met on a cruise in 1993 and have taken 16 cruises with Windstar.
According to Janet Bava, Windstar’s chief commercial officer, 80 percent of the passengers on Windstar’s inaugural mystery cruise were repeat guests. Many of them have already booked a cabin on the company’s next mystery cruise, a round-trip journey starting in San Juan, Puerto Rico, in March 2026.
“If you want to plan something, it’s not your cruise,” Prelog said, noting that even meticulous planners would do well to embrace spontaneity sometimes. “We plan our lives to the tee, and sometimes our planning gets in the way. From my perspective, the mystery cruise should take all of that away and celebrate the spontaneous part of being human.”
