Star Collector: Caribbean Explorations
 
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Sat Mar 14, 2026 - Sat Mar 28, 2026,
 14 days
 on Wind Surf
VIEW ALL DATES
Starting from $3,699 USD
ADD TO
WISH LIST
REMOVE
FROM
WISH LIST
VIEW THE JOURNEY
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 Mar 14
Philipsburg, St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sun Mar 15
Falmouth Harbour
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Mar 16
Road Bay
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Mar 17
Soper's Hole
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Mar 17
Jost Van Dyke, Great Harbour
Arrive:  7:00 PM
Depart:  
Watersports Platform: 
Wed Mar 18
Jost Van Dyke, Great Harbour
Arrive:  
Depart:  10:00 PM
Watersports Platform: 
Thu Mar 19
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Fri Mar 20
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Mar 21
Philipsburg, St. Maarten
Arrive:  6:00 AM
Depart:  7:00 PM
Watersports Platform: 
Sun Mar 22
Charlestown
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Mon Mar 23
Roseau
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Tue Mar 24
Mayreau
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Wed Mar 25
Les Saintes
Arrive:  12:00 PM
Depart:  6:00 PM
Watersports Platform: 
Thu Mar 26
Basseterre
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Fri Mar 27
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Mar 28
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.
LEARN MORE →
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 $3,699 per guest
? All-inclusive price from $5,085 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
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
THIS
SAILING
Sat, Mar 21 - Sat, Apr 4, 2026
WIND SURF
$5,085
$3,699