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Star Collector: Caribbean Explorations
 
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Sat Jan 31, 2026 - Sat Feb 14, 2026,
 14 days
 on Wind Spirit
?All-inclusive from
$5,345
?Cruise Only From
$4,099
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Philipsburg, St. Maarten to Philipsburg, St. Maarten
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 Les Saintes, Anse Mitan, Pigeon Island and much more.
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: Road Bay
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.
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Day 7: 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 8: 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 9: 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 10: 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 11: 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 12: 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 13: 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 14: 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 15: 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
Beach Party
Enjoy Windstar’s exclusive Signature Beach Party at Prickly Pear Beach
 
Complimentary laundry
Pack light with complimentary daily laundry service
 
Jost Van Dyke
Overnight in Jost Van Dyke and Virgin Gorda for more in-depth exploration
 
Les Saintes
Absorb the distinctive French charm of enchanting Les Saintes.
Pigeon Island
Anchor alongside the pristine beaches of Pigeon Island’s 40-acre National Park and explore at your leisure
 
St. Kitts
Embrace the island life on St. Kitts’ one-of-a-kind Shipwreck Beach
 
St. Lucia
Discover St. Lucia’s UNESCO site when you see the twin Pitons, rising majestically from the turquoise sea
 
Virgin Gorda
Soak in the natural bathing pools of "The Baths" at Virgin Gorda
 
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Sat Jan 31
Philipsburg, St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sun Feb 1
Soper's Hole
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sun Feb 1
Jost Van Dyke, Great Harbour
Arrive:  7:00 PM
Depart:  
Watersports Platform: 
Mon Feb 2
Jost Van Dyke, Great Harbour
Arrive:  
Depart:  10:00 PM
Watersports Platform: 
Tue Feb 3
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  7:00 AM
Depart:  5:00 PM
Watersports Platform: 
Wed Feb 4
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Thu Feb 5
Road Bay
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Fri Feb 6
Falmouth Harbour
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sat Feb 7
Philipsburg, St. Maarten
Arrive:  6:00 AM
Depart:  7:00 PM
Watersports Platform: 
Sun Feb 8
Charlestown
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Mon Feb 9
Roseau
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Tue Feb 10
Pigeon Island
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Wed Feb 11
Les Saintes
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Thu Feb 12
Gustavia
Arrive:  9:00 AM
Depart:  10:00 PM
Watersports Platform: 
Fri Feb 13
Basseterre
Arrive:  8:00 AM
Depart:  9:00 PM
Watersports Platform: 
Sat Feb 14
Philipsburg, St. Maarten
Arrive:  6:00 AM
Depart:  
Watersports Platform: 
Wind Spirit
The Wind Spirit is a sleek, 4-masted sailing yacht accommodating 148 guests. With four decks and a gross tonnage of 5,736, Wind Spirit feels like your own private yacht.
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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
Every inch of your stateroom is designed for comfort. Luxurious Egyptian cotton linens wrap you in pleasant sleepiness as you stretch out in your queen bed (can be separated into twins if you prefer). Your spacious bath features granite counter tops, ample storage, and a roomy shower with massage shower head. L’Occitane® bath products invite you to indulge, while comfy waffle-weave robe and slippers entice you to relax. You’ll find fresh fruit and flowers always waiting for you after a day of sun or sightseeing. And, of course, everything else you need and expect — flat-screen television and DVD, private safe. And always at your fingertips, anything you wish from room service.
? Cruise only from $4,099 per guest
? All-inclusive price from $5,345 per guest
Category BX Deluxe
Category BX Deluxe
Every inch of your stateroom is designed for comfort. Luxurious Egyptian cotton linens wrap you in pleasant sleepiness as you stretch out in your queen bed (can be separated into twins if you prefer). Your spacious bath features granite counter tops, ample storage, and a roomy shower with massage shower head. L’Occitane® bath products invite you to indulge, while comfy waffle-weave robe and slippers entice you to relax. You’ll find fresh fruit and flowers always waiting for you after a day of sun or sightseeing. And, of course, everything else you need and expect — flat-screen television and DVD, private safe. And always at your fingertips, anything you wish from room service.
? Cruise only from $4,399 per guest
? All-inclusive price from $5,645 per guest
Category A
Category A
Every inch of your stateroom is designed for comfort. Luxurious Egyptian cotton linens wrap you in pleasant sleepiness as you stretch out in your queen bed (can be separated into twins if you prefer). Your spacious bath features granite counter tops, ample storage, and a roomy shower with massage shower head. L’Occitane® bath products invite you to indulge, while comfy waffle-weave robe and slippers entice you to relax. You’ll find fresh fruit and flowers always waiting for you after a day of sun or sightseeing. And, of course, everything else you need and expect — flat-screen television and DVD, private safe. And always at your fingertips, anything you wish from room service.
? Cruise only from $4,599 per guest
? All-inclusive price from $5,845 per guest
Category AX Deluxe
Category AX Deluxe
Every inch of your stateroom is designed for comfort. Luxurious Egyptian cotton linens wrap you in pleasant sleepiness as you stretch out in your queen bed (can be separated into twins if you prefer). Your spacious bath features granite counter tops, ample storage, and a roomy shower with massage shower head. L’Occitane® bath products invite you to indulge, while comfy waffle-weave robe and slippers entice you to relax. You’ll find fresh fruit and flowers always waiting for you after a day of sun or sightseeing. And, of course, everything else you need and expect — flat-screen television and DVD, private safe. And always at your fingertips, anything you wish from room service.
? Cruise only from $4,999 per guest
? All-inclusive price from $6,245 per guest
Owner's Suite
Owner's Suite
With an expansive 220 square feet, the Owner’s Suite gives you everything offered in a stateroom, plus lots more, including a beautiful sitting area and separate in-room dining space.
? Cruise only from $10,999 per guest
? All-inclusive price from $12,245 per guest
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
Complimentary All-Inclusive Upgrade
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited beer, wine, and cocktails, and gratuities. From $89 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sat, Dec 21 - Sat, Jan 4, 2025
WIND SURF
$5,699
$5,699
Sat, Dec 28 - Sat, Jan 11, 2025
WIND SURF
$5,699
$5,699
Sat, Jan 4 - Sat, Jan 18, 2025
WIND SURF
$5,099
$5,099
Sat, Jan 11 - Sat, Jan 25, 2025
WIND SURF
$5,099
$5,099
Sat, Jan 18 - Sat, Feb 1, 2025
WIND SURF
$5,099
$5,099
Sat, Feb 1 - Sat, Feb 15, 2025
WIND SURF
$4,799
$4,799
Sat, Feb 8 - Sat, Feb 22, 2025
WIND SURF
$4,899
$4,899
Sat, Feb 15 - Sat, Mar 1, 2025
WIND SURF
$4,599
$4,599
Sat, Feb 22 - Sat, Mar 8, 2025
WIND SURF
$4,399
$4,399
Sat, Mar 8 - Sat, Mar 22, 2025
WIND SURF
$4,799
$4,799
Sat, Mar 15 - Sat, Mar 29, 2025
WIND SURF
$4,799
$4,799
Sun, Dec 7 - Sun, Dec 21, 2025
WIND SURF
$4,945
$3,699
Sun, Dec 14 - Sun, Dec 28, 2025
WIND SURF
$5,245
$3,999
Sun, Dec 21 - Sun, Jan 4, 2026
WIND SURF
$5,545
$4,299
Sat, Jan 31 - Sat, Feb 14, 2026
WIND SPIRIT
$5,345
$4,099
THIS
SAILING
Sat, Feb 7 - Sat, Feb 21, 2026
WIND SPIRIT
$5,345
$4,099
Sat, Feb 28 - Sat, Mar 14, 2026
WIND SURF
$4,945
$3,699
Sat, Mar 14 - Sat, Mar 28, 2026
WIND SURF
$4,945
$3,699
Sat, Mar 21 - Sat, Apr 4, 2026
WIND SURF
$4,945
$3,699