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2026 President’s Mystery Cruise

San Juan to San Juan

Fri Mar 20, 2026 - Fri Mar 27, 2026,

7 days

on Star Seeker

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OVERVIEW

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San Juan to San Juan

Join Windstar Cruises President, Chris Prelog, for an unforgettable 7-night roundtrip voyage from San Juan aboard the brand-new Star Seeker during her inaugural season. This exclusive Caribbean journey takes you to hidden gems and smaller islands, where you can unwind on pristine beaches and make the most of Star Seeker’s Marina—allowing you to swim from the ship and relax in the water. Adding to the excitement, each day’s destination will be revealed just 36 hours before arrival, making every stop a thrilling surprise. A journey with Windstar isn’t just about where you’re going—it’s about who you’re sailing with. When you cruise with us, you’re part of the Windstar family, welcomed with warm hospitality and thoughtful service at every turn. This is your chance to experience Windstar’s brand-new Star Seeker in the Caribbean before she sets sail for Alaska and Asia—don’t miss this one-of-a-kind adventure!

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Day 1: San Juan

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.

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Day 2: Mystery Port 1

Today is a surprise! Prepare to be captivated as anticipation builds with the unveiling of our mystery port, revealed only 36 hours before our ship arrives at its destination. Rest assured that you’ll still explore new places, meet amazing people and make unforgettable memories — because that’s what you do on a Windstar cruise.

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Day 3: Mystery Port 2

Today is a surprise! Prepare to be captivated as anticipation builds with the unveiling of our mystery port, revealed only 36 hours before our ship arrives at its destination. Rest assured that you’ll still explore new places, meet amazing people and make unforgettable memories — because that’s what you do on a Windstar cruise.

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Day 4: Mystery Port 3

Today is a surprise! Prepare to be captivated as anticipation builds with the unveiling of our mystery port, revealed only 36 hours before our ship arrives at its destination. Rest assured that you’ll still explore new places, meet amazing people and make unforgettable memories — because that’s what you do on a Windstar cruise.

VIEW THE JOURNEY

Day 5: Mystery Port 4

Today is a surprise! Prepare to be captivated as anticipation builds with the unveiling of our mystery port, revealed only 36 hours before our ship arrives at its destination. Rest assured that you’ll still explore new places, meet amazing people and make unforgettable memories — because that’s what you do on a Windstar cruise.

VIEW THE JOURNEY

Day 6: Mystery Port 5

Today is a surprise! Prepare to be captivated as anticipation builds with the unveiling of our mystery port, revealed only 36 hours before our ship arrives at its destination. Rest assured that you’ll still explore new places, meet amazing people and make unforgettable memories — because that’s what you do on a Windstar cruise.

VIEW THE JOURNEY

Day 7: Mystery Port 6

Today is a surprise! Prepare to be captivated as anticipation builds with the unveiling of our mystery port, revealed only 36 hours before our ship arrives at its destination. Rest assured that you’ll still explore new places, meet amazing people and make unforgettable memories — because that’s what you do on a Windstar cruise.

VIEW THE JOURNEY

Day 8: San Juan

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.

Popular Highlights

Experience brand new Star Seeker during her first season in the Caribbean.

Explore several new-to-Windstar locations.

Windstar’s President

Meet and sail with Christopher Prelog, Windstar’s President.

Itinerary at a Glance

Date

Port

Arrive

Depart

MarinaWatersports Platform:

Fri Mar 20

San Juan

Arrive:

Depart: 7:00 PM

Watersports Platform:

Sat Mar 21

Mystery Port 1

Arrive: 8:00 AM

Depart: 11:00 PM

Watersports Platform:

Sun Mar 22

Mystery Port 2

Arrive: 8:00 AM

Depart: 11:00 PM

Watersports Platform:

Mon Mar 23

Mystery Port 3

Arrive: 8:00 AM

Depart: 11:00 PM

Watersports Platform:

Tue Mar 24

Mystery Port 4

Arrive: 8:00 AM

Depart: 11:00 PM

Watersports Platform:

Wed Mar 25

Mystery Port 5

Arrive: 8:00 AM

Depart: 11:00 PM

Watersports Platform:

Thu Mar 26

Mystery Port 6

Arrive: 8:00 AM

Depart: 11:00 PM

Watersports Platform:

Fri Mar 27

San Juan

Arrive: 7:00 AM

Depart:

Watersports Platform:

SEE EXPANDED ITINERARY AND SHORE EXCURSIONS

Accommodations & Pricing

Oceanview Suite

Oceanview Suite

Experience the perfect blend of style and functionality in this thoughtfully designed 203-square-foot suite. The well-planned layout creates an ideal retreat with plenty of natural light, a view of the sea, a walk-in mosaic glass shower and an inviting queen bed (convertible into two twins if desired), perfect for unwinding after a day of fun and exploration.

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Infinity Suite

This 280-square-foot suite features a wide floor-to-ceiling infinity window that allows for stunning ocean views. You can even open the top half to enjoy the cool ocean breeze. Your suite features an inviting queen bed (convertible into two twin beds if desired), a walk-in mosaic glass shower and a comfortable living area where you can lounge and enjoy the view.

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Vista Infinity Suite

Vista Infinity Suite

Located on deck 7, this 280-square-foot suite features a wide floor-to-ceiling infinity window that allows for stunning ocean views. You can even open the top half to enjoy the cool ocean breeze. Your suite features an inviting queen bed (convertible into two twin beds if desired), a walk-in mosaic glass shower and a comfortable living area where you can lounge and enjoy the view.

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Veranda Suite

Stylish comfort and ocean views welcome you to this 225-square-foot suite. Relax on your queen bed (convertible into two twin beds if desired) or lounge in the nearby living area. The outdoor space adds another 55 square feet, enough to sit outside comfortably and enjoy the breeze. In the bathroom, you’ll find a luxurious walk-in mosaic glass shower with rain head and body jets.

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Premier Veranda Suite

Premier Veranda Suite

Located at the middle of the ship, these 225-square-foot suites welcome you with stylish comfort and beautiful ocean views. Relax on your queen bed (convertible into two twin beds if desired) or lounge in the nearby living area. The outdoor space adds another 55 square feet, enough to sit outside comfortably and enjoy the breeze. In the bathroom, you’ll find a luxurious walk-in mosaic glass shower with rain head and body jets.

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Triple Premier Veranda Suite

Triple Premier Veranda Suite

Located on deck 6, this 246-square-foot suite welcomes you with stylish comfort and stunning ocean views. Featuring an inviting queen bed (convertible into two twin beds if desired) and a pull-out sofa in the living area, the suite allows for triple occupancy. The outdoor space adds another 55 square feet, enough to sit outside comfortably and enjoy the breeze. In the bathroom, you’ll find a luxurious walk-in mosaic glass shower with rain head and body jets.

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Triple Infinity Suite

Triple Infinity Suite

This roomy 301-square-foot suite features a wide floor-to-ceiling infinity window in the bedroom, allowing for stunning ocean views. You can even open the top half to enjoy the cool ocean breeze. This suite also features an inviting queen bed (convertible into two twin beds if desired) and a pull-out sofa in the separate living area, allowing for triple occupancy. In the bathroom, you’ll find a luxurious walk-in mosaic glass shower with rain head and body jets.

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Vista Veranda Suite

Vista Veranda Suite

Located on deck 7, this 268-square-foot suite welcomes you with stylish comfort and stunning ocean views. Relax on your queen bed (convertible into two twin beds if desired) or lounge in the nearby living area. The outdoor space adds another 55 square feet, enough to sit outside comfortably and enjoy the breeze. In the bathroom, you’ll find a luxurious walk-in mosaic glass shower with rain head and body jets.

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Deluxe Suite

This 288-square-foot suite welcomes you with spectacular views, courtesy of the sliding glass doors that lead out to your private balcony. The outdoor space adds another 110 square feet, enough to sit outside comfortably and enjoy the breeze. The bedroom features an inviting queen bed and its own sliding glass door with balcony access, while the bathroom includes a luxurious walk-in mosaic glass shower with rain head and body jets.

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Classic Suite

Step into a stylish and bright open living area with a spacious adjacent bedroom. This 353-square-foot suite welcomes you with spectacular views, courtesy of the sliding glass doors that lead out to your private balcony. The outdoor space adds another 110 square feet, enough to sit outside comfortably and enjoy the breeze. The bedroom features an inviting queen bed that can be converted into two twins if desired, while the bathroom includes a luxurious walk-in mosaic glass shower with rain head and body jets.

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Star Suite

Step into a stylish and bright open living area with a spacious adjacent bedroom. This 380-square-foot suite welcomes you with spectacular views, courtesy of the sliding glass doors that lead out to your private balcony. The outdoor space adds another 110 square feet, enough to sit outside comfortably and enjoy the breeze. The bedroom features an inviting queen bed (convertible into two twin beds if desired) and its own sliding glass door with balcony access, while the bathroom includes a bathtub and walk-in mosaic glass shower with rain head and body jets.

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Horizon Owner’s Suite

Horizon Owner’s Suite

This luxurious 548-square-foot suite combines floor-to-ceiling windows and a wrap-around balcony for an unparalleled cruising experience. Perfect for evening cocktails or a private dinner, the wrap-around balcony adds 248 square feet of space and offers unobstructed views of the sea. The suite boasts a separate entryway — as well as separate dining and living areas — and a guest powder room. The bedroom includes an inviting king bed (convertible into two XL twin beds if desired), and the bathroom features a luxurious double walk-in mosaic glass shower with rain head and body jets. For family bookings, the adjacent suite can be combined to provide extra bedrooms and space for entertaining.

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The Windstar Life

The Windstar staff-to-guest ratio is 1:1.5, and it shows.The moment you board you’ll feel it: an ever-attentive crew at your service, providing you with what you want and need, when you want and need it.

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Friendly and Relaxed Atmosphere

Signature Onboard Barbecue

Cooking Demonstrations