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Masterpieces at Sea: Gems of the Leeward Islands
Oct 28, 2026 — Nov 8, 2026
Starting from
7-For-7:
DATA ART TEST PROMO
SAN JUAN → SAN JUAN
11 Nights on Star Pride
On your Caribbean voyage to the Leeward Islands, everywhere you look is another cover shot image. Dazzling white sand turns the shallows mesmerizing shades of peacock and mermaid, weathered fortresses point canons at long-vanished schooners, natural pools warm gently under the mid-day sun. On your private yacht, 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 delightful boutiques. Thank your lucky Star Pride for bringing you here.




Popular Highlights
Delve into the history of pirates and colonists in San Juan.
On Antigua, explore Nelson’s Dockyard, the only Georgian dockyard in the world.
Absorb the distinctive French charm of enchanting Les Saintes.
Enjoy your day on Jost Van Dyke and let the azure waters wash your cares away.
Sail past the stunning emerald Pitons on St. Lucia, a UNESCO World Heritage Site.
Mingle with the glitterati in St. Barts.
Discover the culinary delights of both the Signature Beach Party and the Signature Onboard Barbecue.
Sail, swim and kayak from your yacht’s Marina Platform.

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.
San Juan: Old San Juan Natl Historic Parks Walking Tour with Transfer to Airport
San Juan, Concierge Collection: Half Day Private SUV with Guide
San Juan: Old San Juan Natl Historic Parks Walking Tour with Transfer to Windstar Hotel
San Juan: Rainforest Eco Wonder Tour with Transfer to Airport
San Juan: Rainforest Eco Wonder Tour with Transfer to Windstar Hotel
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
St. John, Champagne Catamaran Sail
St. John, Island tour Featuring Annaberg Ruins
St. John, Trunk Bay Snorkeling Experience
St. John, Lind Point Trail Eco Hike
St. John, Champagne Catamaran Sail

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.
St Barts, Concierge Collection: St. Barthelemy Beach Day
Gustavia, Concierge Collection: Jet Ski
St. Barts: Intimate Island Tour
Gustavia, Concierge Collection: Scuba Dive 1 Tank
St. Barts: Independent Explorer by Car
St. Barts: Sailing Catamaran Adventure
Gustavia, Concierge Collection: Scuba Dive 2 Tank
St. Barts, Concierge Collection: Sunset Cruise
Gustavia, Concierge Collection: Savor St Barts

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.
Basseterre, Island History & Rum Tasting
Basseterre: Sky Safari Zipline Adventure
Basseterre: Snorkel Safari
Basseterre: St Kitts Quad ATV Adventure
Basseterre, Brimstone Hill Fortress & Fairview Great House
Basseterre: Caribbean Scenic Railway
Basseterre, Nevis Panoramic and Beach Tour
Basseterre, Concierge Collection: Caribbean Cooking, History & Folklore in St. Kitts

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.
Falmouth Harbour, Swim with the Stingrays
Falmouth Harbour, Open Course Canopy Zipline
Falmouth Harbour, Nelsons Dockyard Walking Tour & Boat around English Harbour
Falmouth Harbour, Presidents Tour
Falmouth Harbour, Make Your Own Rum
Falmouth Harbour, Concierge Collection, Jet Ski Adventure
Falmouth Harbour, Spectacular Antigua Island Tour
Falmouth Harbour, Antigua Beach Escape *


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.
Les Saintes, Terre de Haut Panoramic Tour
Les Saintes, Relax & Snorkel *

Les Saintes, Explore Terra de Haut by Foot
Les Saintes, Historic Tastes & Treasures of Fort Napoleon
Les Saintes, Blue Escape Kayaking *

Les Saintes, Sample Culinary Treasures of Guadeloupe
Les Saintes, Sailing the Bay
Les Saintes, Snorkel Experience in Les Saintes *


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.
Pigeon Island, Panoramic St. Lucia
Pigeon Island, Rainforest Canopy Zip Line Adventure
Pigeon Island, Aerial Tram Park
Pigeon Island, St. Lucian Walking Food Tour
Pigeon Island, Concierge Collection: Half Day Private Car & Guide
Pigeon Island, Concierge Collection: Full Day Private Car & Guide
Pigeon Island, Concierge Collection: Full Day Private Van & Guide
Pigeon Island, Concierge Collection: Half Day Private Van & Guide
Pigeon Island, Catamaran Cruise to the Pitons
Pigeon Island, Discover Sailing
Pigeon Island, Sweet Honey Bee Tour

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.
St. Georges, Certified Two-Tank Dive
St. Georges, Fort Frederick Rainforest & Waterfall
St. Georges, Certified One-Tank Dive
St. Georges, Sailing Cruise to the Statue Park
St. Georges, Powerboat & Snorkeling at the Statues Park *

St. Georges, Clear Bottom Kayaking
St Georges, Spice of Our Lives
St. Georges, Discover Scuba
St. Georges, Izzie's Great House Discovery

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.
Jost Van Dyke, Catamaran Cruise & Swim to Norman Island

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
Virgin Gorda: Highlights & Bath Tour
Virgin Gorda: Snorkel Adventure

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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