Windstar Launches 2026 Caribbean Mystery Cruise
Windstar Cruises has unveiled a new “mystery cruise” for 2026 that promises to deliver surprise and excitement for adventurous travelers. The seven-night President’s Mystery Cruise departs round trip from San Juan, Puerto Rico, aboard Star Seeker—one of the line’s newest yachts—during its inaugural Caribbean season. Hosted by Windstar’s president, Chris Prelog, the itinerary remains top secret until 36 hours before each port of call, when guests receive the reveal that turns anticipation into discovery at sea.
Windstar’s mystery cruise builds on the success of the line’s first-ever surprise voyage, which sailed round trip from Athens to ports in Italy and Greece. For this Caribbean edition, travelers will embark in Puerto Rico without knowing which islands or hidden gems await them. Destinations could include secluded cays, historic colonial towns, vibrant local markets or snorkeling spots rich with marine life. The element of the unknown transforms every moment into an immersive experience, as passengers rely on the crew’s clues and insider insights rather than guidebooks.
Guests who secure their cabins by June 30 will enjoy a fully inclusive experience at no additional charge. The complimentary package covers unlimited select wine, beer and cocktails, onboard gratuities for all service staff, and Wi-Fi access throughout the voyage, ensuring that travelers can share their surprise discoveries in real time. Members of Windstar’s Yacht Club loyalty program will save an extra five percent on cruise-only fares, adding extra incentive for frequent guests to join the adventure.
Star Seeker’s design enhances the mystery cruise concept with open-deck lounges, al fresco dining venues and intimate bars that encourage spontaneous gatherings and celebrations. The yacht’s compact size allows for docking in smaller harbors that mega-ships cannot reach, granting access to off-the-beaten-path destinations beloved by experienced sailors. Spacious staterooms, panoramic windows and outdoor whirlpools provide private retreats where travelers can reflect on each day’s revelations or plan for the next surprise.
Windstar’s shore team also plays a crucial role in maintaining the mystery. Local guides prepare authentic, small-group experiences, from farm-to-table tastings to hands-on cultural workshops. Those who crave active exploration can opt for kayaking through mangrove lagoons, hiking tropical trails or diving shipwrecks. Other guests might prefer a seaside spa treatment or a sunset cocktail as the yacht slips into the next undisclosed port. Regardless of each day’s call, all excursions are designed to highlight the natural beauty and heritage of the Caribbean islands while preserving the secret until guests arrive.
By combining luxury yacht amenities with the intrigue of a mystery itinerary, Windstar aims to attract travelers eager for something beyond standard cruise itineraries. The line’s small-ship ethos—emphasizing personalized service, destination immersion and culinary excellence—provides the perfect framework for a series of surprise voyages. Prelog notes that the mystery cruise concept reflects Windstar’s commitment to innovation in experiential travel. “Our guests crave experiences that resonate on a deeper level,” he says. “By unveiling destinations at sea, we create a sense of discovery that extends beyond the shoreline into a transformative journey.”
With only a limited number of cabins available, the President’s Mystery Cruise is expected to sell out quickly. Interested travelers are encouraged to reserve their spots early through Windstar Cruises’ website or by contacting their preferred travel advisor. As Windstar’s newest ship embarks on its first Caribbean season, the 2026 mystery voyages promise to redefine how guests experience the region’s hidden treasures, one surprise port at a time.
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