Gems of the Leeward Islands
 
San Juan to San Juan
Fri Mar 27, 2026 - Mon Apr 6, 2026,
 10 days
 on Star Seeker
?All-inclusive from
$3,799
?Cruise Only From
$3,799
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San Juan to San Juan
With 10 days instead of the usual 7,  on this cruise you have time to take in the full measure of this most iconic parts of the Caribbean. Everywhere you look is another cover shot image. Dazzling white sand turns the shallows mesmerizing shades of peacock and mermaid, weathered fortresses point cannons at long-vanished schooners, natural pools warm gently under the mid-day sun. On your private ship, you’re equally at home in exclusive harbors and anchored off barefoot beaches, so you can see it all. Snorkel or dive on vibrant coral reefs. Follow your siren inland to rainforest adventures or duty-free boutiques. Thank your lucky Star Pride for bringing you here.

 
voyage map
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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: CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
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Day 3: St. John's
St. John’s is a city of Old World charm and elegance which lingers in the varied architecture of Georgian, Victorian, Vernacular, Romantic and International flavors.  The picturesque seafront where tiny, colorful boats are moored, the cheerful wooden buildings carefully refurbished to retain their original features, the vibrant Market Street offering vegetables, fruit and fish and the duty-free Heritage Quay shopping area provide a delightful atmosphere to captivate you.  Sites to see include St. John’s Cathedral with its white Baroque towers, the Botanical Garden, St. John’s Antigua Lighthouse, and Fort James.
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Day 4: Les Saintes
This is the Caribbean as you’ve always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.
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Day 5: Pigeon Island
The UNESCO site Pitons’ with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.
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Day 6: St. George's
Inhale the intoxicating aroma of the “Isle of Spice” as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.
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Day 8: Gustavia
Affectionately known as St. Barts, the Caribbean’s most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island’s signature ti punch as kite surfers fly by.
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Day 9: Jost Van Dyke, Great Harbour
For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis  Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor.
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Day 10: Virgin Gorda / Prickly Pear, British Virgin Islands
The  beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns
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Day 11: 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
Beach Party
Discover the culinary delights of both the Signature Beach Party and the Signature Onboard Barbecue.
Les Saintes
Absorb the distinctive French charm of enchanting Les Saintes.
Nelsons Dockyard
Explore Nelson’s Dockyard, the only Georgian dockyard in the world.
St. Barts
Mingle with the glitterati in St. Barts.
St. Lucia Pitons
Cruise past the stunning emerald Pitons (volcanic spires) on St. Lucia - a UNESCO World Heritage Site.
Watersports Platform
Sail, swim, and kayak off the Watersports Platform.
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Fri Mar 27
San Juan
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sat Mar 28
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sun Mar 29
St. John's
Arrive:  9:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Mar 30
Les Saintes
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Mar 31
Pigeon Island
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Wed Apr 1
St. George's
Arrive:  11:00 AM
Depart:  6:00 PM
Watersports Platform: 
Thu Apr 2
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Apr 3
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Apr 4
Jost Van Dyke, Great Harbour
Arrive:  8:00 AM
Depart:  11:59 PM
Watersports Platform: 
Sun Apr 5
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Mon Apr 6
San Juan
Arrive:  7:00 AM
Depart:  
Watersports Platform: 
Star Seeker
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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.
? Cruise only from $3,799 per guest
? All-inclusive price from $3,799 per guest
Infinity Suite
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.
? Cruise only from $4,099 per guest
? All-inclusive price from $4,099 per guest
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.
? Cruise only from $4,299 per guest
? All-inclusive price from $4,299 per guest
Veranda Suite
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.
? Cruise only from $4,699 per guest
? All-inclusive price from $4,699 per guest
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.
? Cruise only from $5,049 per guest
? All-inclusive price from $5,049 per guest
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.
? Cruise only from $5,199 per guest
? All-inclusive price from $5,199 per guest
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.
? Cruise only from $5,199 per guest
? All-inclusive price from $5,199 per guest
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.
? Cruise only from $5,299 per guest
? All-inclusive price from $5,299 per guest
Deluxe Suite
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 (convertible into two twin beds if desired) 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.
? Cruise only from $6,399 per guest
? All-inclusive price from $6,399 per guest
Classic Suite
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.
? Cruise only from $7,499 per guest
? All-inclusive price from $7,499 per guest
Star Suite
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.
? Cruise only from $7,699 per guest
? All-inclusive price from $7,699 per guest
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.
? Cruise only from $8,899 per guest
? All-inclusive price from $8,899 per guest
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.
Friendly and Relaxed Atmosphere
Signature Onboard Barbecue
Cooking Demonstrations
Genuine and Thoughtful Crew
Crew Talent Show
Open Bridge
Local and Live Performances
Relax at the Pool or Hot Tub
Complimentary 24 Hour Room Service
Signature Sail Away
Shopping With The Chef
Take In The Sun
Watersports Platform
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session
ALL DATES &
FARES
Early Booking Offer 2026
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited beer, wine, and cocktails, and gratuities. From $89 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Fri, Mar 27 - Mon, Apr 6, 2026
STAR SEEKER
$3,799
$3,799
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SAILING