Due to popular demand, Windstar Cruises will offer a second Mystery Cruise where the ports aren’t announced and guests receive hints at ports they will visit 36 hours before arrival.
Windstar’s first President’s Mystery Cruise took place from April 19-27, 2025 in the Mediterranean. The cruise line’s second one will take place in the Caribbean and depart on March 20, 2026.
The cruise will depart from San Juan, Puerto Rico and visit the Caribbean. It will take place on Windstar’s new cruise ship, Star Seeker.
36 hours before arriving a port, guests are given hints to the port they will be visiting next. Shore excursion options that range from urban history to countryside rambles are offered in each destination.
The cruise is nearly sold out and has outpaced nearly all of the other cruise line’s bookings for 2026. Windstar Cruises plans on having a waitlist for anyone wanting to take this cruise after it sells out.
The cruise line said that this showcases the incredible excitement and demand for spontaneous travel experiences paired with their trusted service and expertise.
Chris Prelog, president of Windstar Cruises, said the following:
“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.
“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.”
Windstar said that their cruisers can expect more itineraries like this in the future.
