Following the success of its inaugural President’s Mystery Cruise in April 2025, Windstar has announced a second voyage under this concept, scheduled for March 20th, 2026. This upcoming cruise will take place aboard the line's newest vessel, Star Seeker, and will depart from San Juan, Puerto Rico, exploring undisclosed destinations in the Caribbean.
The initial Mystery Cruise, an 8-day journey aboard Star Legend, departed from Athens (Piraeus, Greece) and featured ports that were revealed to guests only 24 hours before arrival. This approach introduced passengers to new destinations, including Taranto and Reggio Calabria in Italy, and Kalamata in Greece, which had not been previously visited by Windstar. The positive reception of this spontaneous travel experience has led to the development of the upcoming Caribbean itinerary.
Star Seeker, set to join Windstar's fleet in December 2025, will offer a range of itineraries across the Caribbean, Alaska, and Japan. The ship's inaugural voyage will commence on December 28, 2025, from Malaga, Spain, culminating in Miami, Florida, on January 13, 2026. Following its christening in Miami, Star Seeker will embark on an eight-day Caribbean voyage from Miami to San Juan, with stops in the Dominican Republic and the British Virgin Islands. The vessel will continue its Caribbean season before transiting the Panama Canal en route to Alaska.
The 2026 Mystery Cruise has garnered significant interest, with bookings nearly sold out shortly after its announcement. This enthusiasm reflects a growing demand for unique and adventurous travel experiences. Windstar Cruises plans to continue offering such itineraries, combining the allure of undisclosed destinations with the comfort and service of its luxury fleet.