Star Collector: Ivory Beaches & Sapphire Seas of the Caribbean
 
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Tue Dec 2, 2025 - Sun Dec 14, 2025,
 12 days
 on Wind Surf
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Starting from $3,399 USD
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Philipsburg, St. Maarten to Philipsburg, St. Maarten
Escape on an extraordinary tropical vacation on this twelve-day cruise to hidden harbors and secluded beaches throughout the Lesser Antilles in the Caribbean. Board a catamaran bound for Norman Island off Tortola and listen to pirate legends and treasure tales prior to your secluded snorkeling excursion among pristine reefs and tropical fish. Set a course in your own rigid inflatable boat (RIB) across bays and inlets near Jost Van Dyke before hopping off for swimming and snorkeling near Great Harbour's scenic coastline. Cast deep lines for tuna, mahi-mahi, barracudas, and other delicious blue-water trophies off Nevis. Sample the sweetest of amber island ingredients in the thoughtful company of eco-minded beekeepers on St. Lucia. Admire sweeping harbor views as you sip local island rum with sweet cakes on a tasting tour of Fort Napoleon above Les Saintes. Sip Dominica’s Sea Moss non-alcoholic seaweed drink. Indulge your senses in classic Cuban cigars paired with spirits, wines, and cocktails at Basseterre, on St. Kitts.
voyage map
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Day 1: Philipsburg, St. Maarten
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.
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Day 2: Soper's Hole
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. 
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Day 2: 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 3: 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 4: 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. 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
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Day 5: 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 6: Philipsburg, St. Maarten
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.
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Day 7: Charlestown
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.
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Day 8: Roseau
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.
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Day 9: Mayreau
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.
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Day 10: 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 11: 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 12: 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.
VIEW THE JOURNEY
Day 13: Philipsburg, St. Maarten
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.
Popular Highlights
Champagne Beach
Snorkel alongside brilliant parrot fish in the bubbly waters of Dominica’s Champagne Beach.
Complimentary laundry
Pack light with complimentary daily laundry service
 
Fort Napoleon
Find the 19th century Fort Napoleon overlooking Les Saintes bay
Pinney’s Beach
Enjoy the unspoiled paradise of Pinney’s Beach where Nevis volunteers tag sea turtles at night
Pusser’s Landing
Stroll Pusser’s Landing, the charming boardwalk of Soper’s Hole on your way to a secluded beach
St. Kitt’s
Embrace the island life on St. Kitt’s one-of-a-kind Shipwreck Beach
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Tue Dec 2
Philipsburg, St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Wed Dec 3
Soper's Hole
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Dec 3
Jost Van Dyke, Great Harbour
Arrive:  7:00 PM
Depart:  
Watersports Platform: 
Thu Dec 4
Jost Van Dyke, Great Harbour
Arrive:  
Depart:  10:00 PM
Watersports Platform: 
Fri Dec 5
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sat Dec 6
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sun Dec 7
Philipsburg, St. Maarten
Arrive:  6:00 AM
Depart:  7:00 PM
Watersports Platform: 
Mon Dec 8
Charlestown
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Tue Dec 9
Roseau
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Wed Dec 10
Mayreau
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Thu Dec 11
Les Saintes
Arrive:  12:00 PM
Depart:  6:00 PM
Watersports Platform: 
Fri Dec 12
Basseterre
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Dec 13
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sun Dec 14
Philipsburg, St. Maarten
Arrive:  6:00 AM
Depart:  
Watersports Platform: 
Wind Surf
On any day, our 342-guest flagship, Wind Surf, the world’s largest sailing ship, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. During their cruise, you will find the perfect setting for ‘making an entrance’ in the beautiful reception area – and, appropriately, that’s only the beginning.
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Accommodations & Pricing
Boutique cruising with fewer than 350 guests. Our expertly designed itineraries and unexpected shore excursions bring you closer to each destination.
Category B
Category B
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $3,399 per guest
? All-inclusive price from $4,587 per guest
Category BX Deluxe
Category BX Deluxe
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $3,599 per guest
? All-inclusive price from $4,787 per guest
Category A
Category A
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $3,799 per guest
? All-inclusive price from $4,987 per guest
Category AX Deluxe
Category AX Deluxe
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $4,199 per guest
? All-inclusive price from $5,387 per guest
Category TX Deluxe
Category TX Deluxe
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $4,999 per guest
? All-inclusive price from $6,187 per guest
Suite
Suite
With 376 square feet, you’ll find the perfect space for time together — and plenty of room for time to yourself. You’ll even enjoy two full separate bathrooms. All the amenities of the staterooms await you, plus a beautiful sitting area, and two flat-screen television sets with DVD players.
? Cruise only from $8,799 per guest
? All-inclusive price from $9,987 per guest
Officer's Suite
Officer's Suite
For the ultimate in nautical experiences, reserve the new Officer’s Suite located close to the Bridge where our own ship’s officers have their quarters. With its unique “insider” location and 242 square feet of comfort, the nautically appointed Officer’s Suite offers an experience you won’t find on any other cruise line.
? Cruise only from $9,299 per guest
? All-inclusive price from $10,487 per guest
Bridge Suite
Bridge Suite
The ultimate in space and style surrounds you in 495 square feet of pure indulgence. Separate bedroom and living room with an in-suite dining area is an invitation to relaxation. And possibly best of all, your expansive bathroom features both a whirlpool spa tub and a massage shower.
? 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
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
Tue, Dec 2 - Sun, Dec 14, 2025
WIND SURF
$4,587
$3,399
THIS
SAILING