Gems of the Leeward Islands
 
San Juan to San Juan
Fri Mar 27, 2026 - Mon Apr 6, 2026,
 10 days
 on Star Seeker
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Starting from $4,099 USD
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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
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.
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports 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 $4,099 per guest
? All-inclusive price from $5,089 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
ALL DATES &
FARES
Early Booking Offer 2026 & 2027
Pick Your Perk
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited select beer, wine, and cocktails, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Fri, Mar 27 - Mon, Apr 6, 2026
STAR SEEKER
$5,089
$4,099
THIS
SAILING
Wed, Oct 28 - Sun, Nov 8, 2026
STAR PRIDE
$3,599
$3,599