Where are we going? Your guess is as good as mine. A secret cruise to mystery ports has proved its appeal to guests of Windstar Cruises.
An inaugural President’s Mystery Cruise on Star Legend in the Mediterranean was so popular the line is doing another 2026. The sold out journey from Athens in April, 2025 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 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.
Onboard, passengers were given a clue to the identity of each port about 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.
Following muses in the sky on deck of Star Legend–Photo by Wallace Immen
“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 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 the 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 here.
Windstar’s next Mystery Cruise, that’s 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.
Guests can expect more itineraries like this from Windstar in the future. Details are on Windstar’s mystery cruise website.
Wallace Immen, The Cruisington Times
