This Cruise Line’s ‘Secret Itinerary’ Trip Has Travellers Guessing Until the Last Minute

If you love surprises and the thrill of the unknown, Windstar Cruises has crafted the perfect getaway. Their unique 7-night President’s Mystery Cruise returns in 2026, sailing round-trip from San Juan, Puerto Rico—and you won’t know the destinations until just 36 hours before each arrival.

After the success of the inaugural Mediterranean version in 2025, Windstar is bringing the concept to the Caribbean aboard their newest ship, Star Seeker, for a sailing that promises spontaneity, luxury, and immersive travel experiences.

A simplified map of the Caribbean Sea highlighting Puerto Rico and its capital, San Juan, with a series of nearby islands marked by question marks. The question marks suggest a mystery or quiz element, likely prompting viewers to identify the surrounding Caribbean islands. The map emphasizes geographical context with minimal labeling for an educational or interactive purpose.

A Journey Where Every Stop Is a Surprise

This one-of-a-kind cruise turns the itinerary into a daily mystery. Each morning, guests receive clues about where the ship is heading next, with full details only revealed a day and a half before arrival.

Here’s the sailing schedule:

Friday, March 20: Depart San Juan, Puerto Rico (7:00 PM)
Saturday, March 21: Mystery Port 1 (8:00 AM – 11:00 PM)
Sunday, March 22: Mystery Port 2 (8:00 AM – 11:00 PM)
Monday, March 23: Mystery Port 3 (8:00 AM – 11:00 PM)
Tuesday, March 24: Mystery Port 4 (8:00 AM – 11:00 PM)
Wednesday, March 25: Mystery Port 5 (8:00 AM – 11:00 PM)
Thursday, March 26: Mystery Port 6 (8:00 AM – 11:00 PM)
Friday, March 27: Return to San Juan (7:00 AM)

Expect a mix of hidden gems and off-the-beaten-path Caribbean islands, with each stop offering new stories to uncover.

Life Aboard the Star Seeker

Launching in 2026, the Star Seeker is Windstar’s latest addition and your home for the week. The onboard experience blends luxury and relaxation with a casual yacht-style atmosphere.

Spend your days however you please—perhaps with a massage at the World Spa, a morning paddleboarding session off the ship’s Marina, or a cocktail on the sun deck. The ship features al fresco dining at Veranda, open Bridge access to meet the Captain, and evening entertainment including live music in the Lounge.

Windstar’s signature small-ship experience means attentive service, spacious suites, and a friendly atmosphere throughout your voyage.

Shore Excursions Designed to Go Deeper

Each mystery destination features a curated set of shore excursions, designed to connect you with local culture, history, and landscapes. From hands-on culinary experiences and guided heritage walks to nature treks and water-based adventures, there’s something for every type of traveller.

Whether you’re a foodie, an adventurer, or someone who simply wants to meet locals and learn something new, Windstar’s excursions are crafted to be immersive and authentic.

Selling Out Fast

This is not your average Caribbean cruise, and cruisers are taking notice. Windstar reports that this Mystery Cruise is already one of its fastest-selling sailings for 2026, and waitlists are expected once cabins are full.

The combination of surprise, expert service, and all-inclusive comfort is proving to be a powerful draw for travellers looking for something beyond the ordinary.

Final Thoughts

For those who crave adventure without sacrificing comfort, the President’s Mystery Cruise offers the best of both worlds. With every port a surprise and every day bringing something new, it reminds us that sometimes, not knowing where you’re going makes the journey even more exciting.

Would you book a cruise without knowing the itinerary? Share your thoughts in the comments!