Windstar Cruises has wrapped up 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 three entirely new ports for Windstar, including Italy’s Taranto and Reggio Calabria, and Greece’s Kalamata.

The cruise also called at Sicily’s Naxos Giardini, near Taormina, a signature port for the line.

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 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,” said 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, Prelog said.

“This has been such fun,” Prelog continued. “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.

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, according to the company.