Star Collector: Caribbean Explorations

 
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Sat Jan 16, 2027 - Sat Jan 30, 2027,
 14 days
 on Wind Surf
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Starting from $3,999 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
MarinaWatersports Platform: 
Sat Jan 16
Philipsburg, St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sun Jan 17
Road Bay
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Jan 18
Soper's Hole
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Jan 18
Jost Van Dyke, Great Harbour
Arrive:  7:00 PM
Depart:  
Watersports Platform: 
Tue Jan 19
Jost Van Dyke, Great Harbour
Arrive:  
Depart:  10:00 PM
Watersports Platform: 
Wed Jan 20
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Thu Jan 21
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Fri Jan 22
Falmouth Harbour
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sat Jan 23
Philipsburg, St. Maarten
Arrive:  6:00 AM
Depart:  7:00 PM
Watersports Platform: 
Sun Jan 24
Charlestown
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Mon Jan 25
Roseau
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Tue Jan 26
Mayreau
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Wed Jan 27
Les Saintes
Arrive:  12:00 PM
Depart:  6:00 PM
Watersports Platform: 
Thu Jan 28
Basseterre
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Fri Jan 29
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Jan 30
Philipsburg, St. Maarten
Arrive:  6:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar) 
? 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
ALL DATES &
FARES
2026 & 2027 Early Booking Offer
Holiday Sailings
Go All-Inclusive — On Us
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited select beer, wine, and cocktails, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sun, Dec 7 - Sun, Dec 21, 2025
WIND SURF
$4,399
$4,399
Sun, Dec 14 - Sun, Dec 28, 2025
WIND SURF
$5,799
$5,799
Sun, Dec 21 - Sun, Jan 4, 2026
WIND SURF
$8,599
$8,599
Sat, Jan 31 - Sat, Feb 14, 2026
WIND SPIRIT
$6,899
$6,899
Sat, Feb 7 - Sat, Feb 21, 2026
WIND SPIRIT
Call For Availability
Sat, Feb 28 - Sat, Mar 14, 2026
WIND SURF
$5,599
$5,599
Sat, Mar 14 - Sat, Mar 28, 2026
WIND SURF
$5,499
$5,499
Sat, Mar 21 - Sat, Apr 4, 2026
WIND SURF
$5,499
$5,499
Sat, Dec 19 - Sat, Jan 2, 2027
WIND SURF
$4,299
$4,299
Sat, Dec 26 - Sat, Jan 9, 2027
WIND SURF
$4,099
$4,099
Sat, Jan 2 - Sat, Jan 16, 2027
WIND SURF
$3,999
$3,999
Sat, Jan 9 - Sat, Jan 23, 2027
WIND SURF
$3,999
$3,999
Sat, Jan 16 - Sat, Jan 30, 2027
WIND SURF
$3,999
$3,999
THIS
SAILING
Sat, Jan 23 - Sat, Feb 6, 2027
WIND SURF
$4,099
$4,099
Sat, Jan 30 - Sat, Feb 13, 2027
WIND SURF
$4,099
$4,099
Sat, Feb 6 - Sat, Feb 20, 2027
WIND SURF
$4,099
$4,099
Sat, Feb 13 - Sat, Feb 27, 2027
WIND SURF
$4,099
$4,099
Sat, Feb 20 - Sat, Mar 6, 2027
WIND SURF
$4,099
$4,099
Sat, Feb 27 - Sat, Mar 13, 2027
WIND SURF
$4,088
$4,088
Sat, Mar 6 - Sat, Mar 20, 2027
WIND SURF
$4,099
$4,099
Sat, Mar 13 - Sat, Mar 27, 2027
WIND SURF
$4,099
$4,099