Star Collector: Caribbean Explorations
 
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Sat Feb 7, 2026 - Sat Feb 21, 2026,
 14 days
 on Wind Spirit
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Starting from $4,099 USD
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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
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
 
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Sat Feb 7
Philipsburg, St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sun Feb 8
Charlestown
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Mon Feb 9
Roseau
Arrive:  8:00 AM
Depart:  1:00 PM
Watersports Platform: 
Tue Feb 10
Mayreau
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Wed Feb 11
Anse Mitan
Arrive:  7:30 AM
Depart:  2:00 PM
Watersports Platform: 
Thu Feb 12
Basseterre
Arrive:  1:00 PM
Depart:  10:00 PM
Watersports Platform: 
Fri Feb 13
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Feb 14
Philipsburg, St. Maarten
Arrive:  6:00 AM
Depart:  7:00 PM
Watersports Platform: 
Sun Feb 15
St. John's
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Feb 16
Road Bay
Arrive:  9:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Feb 17
Soper's Hole
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Feb 17
Jost Van Dyke, Great Harbour
Arrive:  7:00 PM
Depart:  
Watersports Platform: 
Wed Feb 18
Jost Van Dyke, Great Harbour
Arrive:  
Depart:  10:00 PM
Watersports Platform: 
Thu Feb 19
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Fri Feb 20
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Feb 21
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 $5,485 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
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
Sat, Feb 8 - Sat, Feb 22, 2025
WIND SURF
Call For Availability
Sat, Feb 15 - Sat, Mar 1, 2025
WIND SURF
$8,185
$6,799
Sat, Feb 22 - Sat, Mar 8, 2025
WIND SURF
$6,585
$5,199
Sat, Mar 8 - Sat, Mar 22, 2025
WIND SURF
$8,085
$6,699
Sat, Mar 15 - Sat, Mar 29, 2025
WIND SURF
$8,185
$6,799
Sun, Dec 7 - Sun, Dec 21, 2025
WIND SURF
$5,085
$3,699
Sun, Dec 14 - Sun, Dec 28, 2025
WIND SURF
$5,385
$3,999
Sun, Dec 21 - Sun, Jan 4, 2026
WIND SURF
$5,685
$4,299
Sat, Jan 31 - Sat, Feb 14, 2026
WIND SPIRIT
$5,485
$4,099
Sat, Feb 7 - Sat, Feb 21, 2026
WIND SPIRIT
$5,485
$4,099
THIS
SAILING
Sat, Feb 28 - Sat, Mar 14, 2026
WIND SURF
$5,885
$4,499
Sat, Mar 14 - Sat, Mar 28, 2026
WIND SURF
$5,085
$3,699
Sat, Mar 21 - Sat, Apr 4, 2026
WIND SURF
$5,085
$3,699