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 $3,799 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
Fort-de-France
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
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
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 14, 2025
WIND SURF
$2,699
$2,699
Sun, Dec 21 - Sun, Dec 28, 2025
WIND SURF
$3,399
$3,399
Sat, Feb 7 - Sat, Feb 14, 2026
WIND SPIRIT
$3,799
$3,799
THIS
SAILING
Sat, Feb 28 - Sat, Mar 7, 2026
WIND SURF
$2,899
$2,899
Sat, Mar 21 - Sat, Mar 28, 2026
WIND SURF
$2,599
$2,599
Sat, Dec 26 - Sat, Jan 2, 2027
WIND SURF
$3,392
$2,699
Sat, Jan 9 - Sat, Jan 16, 2027
WIND SURF
$3,192
$2,499
Sat, Jan 23 - Sat, Jan 30, 2027
WIND SURF
$3,292
$2,599
Sat, Feb 6 - Sat, Feb 13, 2027
WIND SURF
$3,292
$2,599
Sat, Feb 20 - Sat, Feb 27, 2027
WIND SURF
$3,292
$2,599
Sat, Mar 6 - Sat, Mar 13, 2027
WIND SURF
$3,292
$2,599
Classic Caribbean
Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
7 days
Day
Port
Day 1
Philipsburg, St. Maarten
Day 2
Charlestown
Day 3
Roseau
Day 4
Mayreau
Day 5
Fort-de-France
Day 6
Basseterre
Day 7
Gustavia
Day 8
Philipsburg, St. Maarten
ALL DATES &
FARES
Holiday Sailings
Go All-Inclusive — On Us
Great cruise-only fares or make it an all-inclusive voyage with unlimited select beer, wine, and cocktails, Wi-Fi, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sun
Dec 7
2025
WIND SURF
$2,699
$2,699
Sun
Dec 21
2025
WIND SURF
$3,399
$3,399
Sat
Feb 7
2026
WIND SPIRIT
$3,799
$3,799
Sat
Feb 28
2026
WIND SURF
$2,899
$2,899
Sat
Mar 21
2026
WIND SURF
$2,599
$2,599
Sat
Dec 26
2026
WIND SURF
$3,392
$2,699
Sat
Jan 9
2027
WIND SURF
$3,192
$2,499
Sat
Jan 23
2027
WIND SURF
$3,292
$2,599
Sat
Feb 6
2027
WIND SURF
$3,292
$2,599
Sat
Feb 20
2027
WIND SURF
$3,292
$2,599
Sat
Mar 6
2027
WIND SURF
$3,292
$2,599
Click on the date to view the map and itinerary by date