Windstar's Inaugural President's Mystery Cruise

Windstar in Italy (Windstar)

(Press Release) MIAMI, FL, May 6, 2025 – Windstar Cruises, one of travel’s leading destination discovery specialists, concluded its inaugural President’s Mystery Cruise, which took place on Star Legend from April 19 – 27 in the Mediterranean. The sold-out journey, which was based from Athens (Piraeus), featured ports of calls that were previously unvisited not only by many of its passengers but also by the line itself; three all-new-to-Windstar ports in the region, including Italy’s Taranto and Reggio Calabria, and Greece’s Kalamata, were on the itinerary. The cruise also called at Sicily’s Naxos Giardini, near Taormina, a signature port for the line. 

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Onboard, passengers were given a clue to the identity of each port some 36 hours before the visit. Shore excursion options that ranged from urban history to countryside rambles were offered in each destination. Special touches included a destination discovery event -- a signature Windstar experience -- on a coastal hilltop in Reggio Calabria, and an invigorating performance of the Tarantella, a romantic dance ritual in Puglia, performed onboard while Star Legend was docked in Taranto. 

“So many of Windstar’s guests are wonderfully adventurous and curious about the world they live in that we wanted to create a trip around the idea of discovering new destinations in a spontaneous fashion,” says Chris Prelog, president of Windstar Cruises, who hosted the sailing. “The Mediterranean offered so many opportunities to venture to places, such as Italy’s Puglia and Calabria, that hadn’t been on their radar – yet.” 

Some of these new ports, such as Reggio Calabria and Taranto, both in Italy’s “boot,” have already been incorporated into 2026 itineraries, he says.

“This has been such fun,” he adds. “Letting go of the daily planning that happens in advance to instead live in the moment and embrace your current destination is thrilling and liberating. I highly recommend it as a new travel experience. We are all ready for the next Mystery Cruise in the Caribbean!” You can read more about Windstar’s first Mystery Cruise on our blog.

Indeed, Windstar’s next Mystery Cruise, which launched last week and is already nearly sold out, will depart on March 20, 2026 aboard the 224-guest Star Seeker, Windstar’s newest yacht. The Caribbean-oriented voyage based from San Juan, Puerto Rico, has outpaced all other 2026 cruise bookings, showcasing the incredible excitement and demand for spontaneous travel experiences paired with Windstar’s trusted service and expertise. It’s without a doubt that guests can expect more itineraries like this from Windstar in the future... 

To embrace the unknown with Windstar’s 2026 Mystery Cruise, or to join the waitlist for those who are eager to join the cruise but aren't able to secure a suite of choice, visit here.

For more information on Star Seeker, visit here.  

To plan a small ship cruise with Windstar book online here, contact a travel advisor, reach out to Windstar Cruises by phone at 866-258-7245, or request a call by a Windstar vacation planner.