Classic Caribbean
 
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Sat Feb 7, 2026 - Sat Feb 14, 2026,
 7 days
 on Wind Spirit
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Starting from $2,699 USD
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Philipsburg, St. Maarten to Philipsburg, St. Maarten
From the stunning drama of the Pitons to the captivating charm of Les Saintes. From hidden coves and secret beaches to exotic markets and lively cafés. Discover the best of this region with one single Caribbean cruise. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.
voyage map
Popular Highlights
Beach Party
Let yourself go – at Windstar’s Signature Beach Party, where the Caribbean spirit is in full swing.
Les Saintes
Savor 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.
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports 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:  
Watersports Platform: 
Accommodations & Pricing
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 $2,699 per guest
? All-inclusive price from $3,392 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
Holiday Sailings
Pick Your Perk
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 14, 2025
WIND SURF
$2,992
$2,299
Sun, Dec 21 - Sun, Dec 28, 2025
WIND SURF
$3,592
$2,899
Sat, Feb 7 - Sat, Feb 14, 2026
WIND SPIRIT
$3,392
$2,699
THIS
SAILING
Sat, Feb 28 - Sat, Mar 7, 2026
WIND SURF
$3,292
$2,599
Sat, Mar 21 - Sat, Mar 28, 2026
WIND SURF
$3,092
$2,399