Gems of the Leeward Islands
 
San Juan to San Juan
Wed Oct 28, 2026 - Sun Nov 8, 2026,
 11 days
 on Star Pride
VIEW ALL DATES
Starting from $3,599 USD
ADD TO
WISH LIST
REMOVE
FROM
WISH LIST
VIEW THE JOURNEY
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: 
Wed Oct 28
San Juan
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Thu Oct 29
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Fri Oct 30
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Oct 31
Basseterre
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sun Nov 1
Falmouth Harbour
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Nov 2
Les Saintes
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Nov 3
Pigeon Island
Arrive:  8:00 AM
Depart:  9:30 PM
Watersports Platform: 
Wed Nov 4
St. George's
Arrive:  10:00 AM
Depart:  6:00 PM
Watersports Platform: 
Thu Nov 5
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Nov 6
Jost Van Dyke, Great Harbour
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Nov 7
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sun Nov 8
San Juan
Arrive:  7:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
Guaranteed Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
? Call for Availability
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
Wed, Oct 28 - Sun, Nov 8, 2026
STAR PRIDE
$3,599
$3,599
THIS
SAILING