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Star Collector: Caribbean Explorations
Jan 23, 2027 — Feb 6, 2027
Starting from
DATA ART TEST PROMO
Free Laundry for Collectors:
PHILIPSBURG, ST. MAARTEN → PHILIPSBURG, ST. MAARTEN
14 Nights on Wind Surf
Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Barbuda, Soper’s Hole in Tortola, Gustavia in St. Barthémy, St. Lucia’s Pigeon Island and much more.






Popular Highlights
Anchor alongside the pristine beaches of Pigeon Island’s 40-acre National Park and explore at your leisure.
Discover St. Lucia’s UNESCO site when you see the twin Pitons, rising majestically from the turquoise sea.
Embrace the island life on St. Kitts’ one-of-a-kind Shipwreck Beach.
Soak in the naturally-formed granite bathing pools of "The Baths" at Virgin Gorda.
Enjoy Windstar’s exclusive Signature Beach Party at Prickly Pear Beach.
Overnight in Jost Van Dyke for more in-depth exploration.
Pack light with complimentary daily laundry service.

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 with Transfer to Windstar Hotel
St. Maarten, Post Island Tour with Transfer to Airport
St. Maarten: Americas Cup Sailboat Racing with Transfer to Airport
St. Maarten, Post Island Tour with Transfer to Hotel

This capital of Nevis with its narrow streets and brightly painted Victorian and Georgian stone buildings is full of colonial history. Alexander Hamilton lived here as a child and you can see the ruins of the Hamilton Estate. Lovely Pinney's Beach is nearby and a group of volunteers work at night tagging sea turtles here and on the other beautiful beaches. Walk the main street and check out the Museum of Nevis History, St. Thomas Lowland Church and the Nevisian Heritage Village to name a few of the historic sites here.
Charlestown, Montravers Hike & Beach Break with Lunch
Charlestown, Coastal Boat Cruise Snorkel Adventure
Charlestown, Quad Biking Adventure
Charlestown, Concierge Collection: Deep Sea Fishing
Charlestown, Yachtsman Grill Beach Escape
Charlestown, Quad Biking Adventure Single
Charlestown, Nevis Half Island & Botanical Garden

Get ready for a full day with plenty to do. Snorkel alongside brilliant parrot fish in the bubbly waters of Champagne Beach. Take a break to enjoy more than 150 species of plants and brilliant red-necked Jaco parrots at the botanical gardens. If you're up for an optional hike, don't miss Boiling Lake and the Valley of Desolation at Dominica's Morne Trois Pitons National Park, a UNESCO World Heritage Site.
Roseau, Dominica in a Day
Roseau, Champagne Reef Snorkel Adventure
Roseau, River Tubing Adventure
Roseau, Indian River Rowboat
Roseau, Concierge Collection: Wet & Rugged Dominica
Roseau, Whale & Dolphin Adventure
Roseau, 4X4 Waterfall & Rainforest
Roseau, Concierge Collection: Cooking Caribbean Flavors & Lifestyles
Roseau, Trafalgar Falls & Hot Springs

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, Terre de Haut Panoramic Tour
Les Saintes, Blue Escape Kayaking *

Les Saintes, Snorkel Experience in Les Saintes *

Les Saintes, Sailing the Bay
Les Saintes, Explore Terra de Haut by Foot
Les Saintes, Relax & Snorkel *

Les Saintes, Sample Culinary Treasures of Guadeloupe
Les Saintes, Historic Tastes & Treasures of Fort Napoleon

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

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

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 with Transfer to Airport
St. Maarten: Americas Cup Sailboat Racing with Transfer to Windstar Hotel
St. Maarten, Post Island Tour with Transfer to Hotel
St. Maarten, Post Island Tour with Transfer to Airport

With its protected shoreline, calm surf, spectacular coral reefs and sugar-soft beaches, Road Bay has become a destination for boaters, with its delightful restaurants, bars, and shops. Anguilla has some of the most beautiful sunsets and delicious rum punch to be found in the Caribbean. It is also home to Cuban tree frogs, red-footed tortoise, green iguanas and five species of bats. Worth checking out is Wallblake House, a heritage plantation house and museum said to be the oldest building on the island and located nearby.
Road Bay, Shoal Bay Beach Transfer
Road Bay, French Invasion Hike
Road Bay, Concierge Collection: Relaxing Day at Savi with Lunch
Road Bay, Island Exploration by Moke
Concierge Collection: Road Bay, Snorkel Adventure by Speedboat
Road Bay, Iconic Island Highlights with Salt Tasting and Beach Time

Arrive at the boardwalk of Pusser's Landing and mingle with other yachtsmen in the utterly charming marina at Soper's Hole. Find a deserted stretch of beach to kick back and ponder this tiny port's rich heritage of romance, pirates, and adventure. An evening departure features a once-in-a-lifetime romantic sunset Sail Away.
Tortola, Scenic Drive & Beach
Soper's Hole: Cane Garden Bay Beach Break
Tortola, Tortola Jeep & Beach Tour
Jost Van Dyke, Catamaran Cruise & Swim to Norman Island
Tortola, Snorkel Adventure at Peter Island

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.

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.

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

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

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, Open Course Canopy Zipline
Falmouth Harbour, Swim with the Stingrays
Falmouth Harbour, Concierge Collection, Jet Ski Adventure
Falmouth Harbour, Presidents Tour
Falmouth Harbour , Concierge Collection, Tuk Tuk Rainforest and Beach
Falmouth Harbour, Spectacular Antigua Island Tour
Falmouth Harbor, Chocolate and Rum Making
Falmouth Harbour, Antigua Beach Escape *

Falmouth Harbour, Nelsons Dockyard Walking Tour & Boat around English Harbour

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.
Staterooms
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