Windstar Unveils Expanded Mystery Cruise Experience with Caribbean Voyage on Star Seeker Ship

Following the success of its first President’s Mystery Cruise in April 2025, Windstar Cruises is set to launch a second voyage on March 20, 2026. This upcoming adventure will take place on the Star Seeker, the line’s newest ship, departing from San Juan, Puerto Rico, and exploring undisclosed Caribbean destinations.

The inaugural Mystery Cruise, which lasted eight days aboard the Star Legend, offered a unique travel experience by revealing ports to guests only 24 hours before arrival. This first journey introduced travelers to lesser-known destinations, including Taranto, Reggio Calabria, and Kalamata, which had not been previously featured in Windstar’s itineraries. The favorable response to this spontaneous travel concept prompted the planning of the new Caribbean itinerary.

Scheduled to join Windstar’s fleet in December 2025, Star Seeker will feature itineraries spanning the Caribbean, Alaska, and Japan. Its inaugural journey will begin on December 28, 2025, from Malaga, Spain, and conclude in Miami, Florida, on January 13, 2026. After its christening in Miami, Star Seeker will embark on an eight-day Caribbean cruise to San Juan, making stops in the Dominican Republic and the British Virgin Islands before continuing its Caribbean season and transiting the Panama Canal to Alaska.

Interest in the 2026 Mystery Cruise is high, with bookings nearly filled shortly after the announcement, highlighting a growing appetite for adventurous and unique travel experiences. Windstar Cruises is committed to continuing such itineraries, blending the excitement of undisclosed ports with the luxury service its fleet is known for.

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