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Star Collector: Lovely Leewards
Dec 27, 2026 — Jan 10, 2027
Starting from
DATA ART TEST PROMO
Free Laundry for Collectors:
SAN JUAN → SAN JUAN
14 Nights on Star Pride
Whether you’re passionate about swimming among undersea wildlife or the intricate cultures and intertwined European histories of the Leeward Islands, this 2-week cruise offers the best combinations of charm, island heritage and natural beauty. Shop unique designer apparel in St. Barts, where you’ll discover a fashionable confluence of high-end brands. Stare in wonder at the glow from miniscule bioluminescent organisms stirred by your kayak paddle during a tour of the Fajardo Bio Bay nature reserve near San Juan. Master the art of cooking with distinct spices like nutmeg, cloves and allspice in authentic Caribbean cuisine while taking direction from a highly-skilled native chef in Philipsburg. This Caribbean getaway is the perfect duration for lovers of island life and those who want to spend more time exploring the Windward Islands overlooked by other cruise lines.







Popular Highlights
Take a stroll in the St. John’s National Park which covers over half of the islands.
Pick up tempting souvenirs at the pastel-colored buildings and shops of duty-free Philipsburg.
Enjoy the spice market and some of the best snorkeling around Grenada, the Spice Island.
The Piton's two volcanic peaks, rising more than 2,400, feet welcome you to St. Lucia.
Walk up Mount Pleasant with a spectacular view of Bequia's Admiral Bay.
Discover the imposing façade of El Morrow Fortress, a UNESCO site in San Juan.
Enjoy a relaxing beach day in St. Barts, long the haunt of the rich.
Pack light with complimentary daily laundry service.

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

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

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

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.
St. Maarten: Americas Cup Sailboat Racing
St. Maarten: Under Two Flags Island Tour
St. Maarten, Concierge Collection: Half Day Private Island Tour in SUV or Deluxe Mini Van
Philipsburg, Savor St. Maarten Foodie Tour

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.
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, Bacardi Rum Tour & Tasting- With Transfer to Windstar Hotel
San Juan: Old San Juan Natl Historic Parks Walking Tour with Transfer to Airport

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, Certified One-Tank Dive
St. Georges, Izzie's Great House Discovery
St. Georges, Powerboat & Snorkeling at the Statues Park *

St Georges, Spice of Our Lives
St. Georges, Sailing Cruise to the Statue Park
St. Georges, Discover Scuba
St. Georges, Clear Bottom Kayaking
St. Georges, Fort Frederick Rainforest & Waterfall
St. Georges, The Best of Grenada

The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia's whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island's famed model boat builders at work on their miniature masterpieces.
Bequia, Concierge Collection: Rum Tasting at Firefly Plantation
Bequia Highlights
Bequia, Taste of Bequia
Bequia Snorkel Adventure
Bequia, Mustique Magic with Lunch
Bequia, Bequia Fort & Lower Beach Getaway *
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With fewer than 300 inhabitants and miles of secluded beaches, it's easy to feel as if you're on your own private island. Saline Bay is a delightful anchorage that separates the Caribbean from the Atlantic - and a perfect place to play with some of the toys from the Watersports Platform.
Mayreau, Grenadines Island 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, Relax & Snorkel *

Les Saintes, Snorkel Experience in Les Saintes *

Les Saintes, Sample Culinary Treasures of Guadeloupe
Les Saintes, Blue Escape Kayaking *

Les Saintes, Explore Terra de Haut by Foot
Les Saintes, Terre de Haut Panoramic Tour
Les Saintes, Historic Tastes & Treasures of Fort Napoleon
Les Saintes, Sailing the Bay
Established around 1689, Marigot is the attractive capital of French St. Martin, with its brightly colored houses, a lively open-air market, secluded beaches, and pretty waterfront promenade. Because of its tax-free status, Marigot is a popular center for duty-free shopping, where all of the world's most prestigious brands can be found. Originally the area was marshy, and surrounded by mangroves. In the 1970s part of the bay was filled in to extend Marigot into a larger city with a marina. Overlooking Marigot is Fort St. Louis, the largest historical monument in St. Martin with an impressive panoramic view of the bay.
Marigot, French Creole Cooking Class
Marigot, French and Dutch Island Discovery
Marigot, Beach Day at KKO With Lunch
Marigot, Rhum and Rhythm

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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