Gems of the Leeward Islands
 
San Juan to San Juan
Wed Oct 28, 2026 - Sun Nov 8, 2026,
 11 days
 on Star Pride
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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: 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 4: Basseterre
With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean’s small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.
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Day 5: Falmouth Harbour
It’s said that Antigua has 365 beaches – one for every day of the year. See how many you can discover as our stay in port stretches into the evening to accommodate them all. Watch the stars come out as darkness falls and imagine how residents of Andromeda must envy you.
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Day 6: 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 7: 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 8: 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 10: 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 11: 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. Although 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.
 
Please note: only guests with shore excursions booked through Windstar can be tendered to Gun Creek.
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Day 12: 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: 
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: 
Star Pride
Carrying only 312 guests, Star Pride still tucks into small ports like Le Lavandou and Wrangell or narrow waterways like the Corinth and Keil Canal. We can’t wait to welcome you onboard for your next 180 degree from ordinary adventure! Learn more about the newly renovated ship and the $250 Million Star Plus Initiative.
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Accommodations & Pricing
This all-suite ship completed renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love.
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
Pick Your Perk
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited 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
Call For Availability
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SAILING