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MY WINDSTAR
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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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Accommodations & Pricing
Classic Caribbean
Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
7 days
Close
Day
Port
Day 1
Philipsburg, St. Maarten
Day 2
Charlestown
Day 3
Roseau
Day 4
Mayreau
Day 5
Anse Mitan
Day 6
Basseterre
Day 7
Gustavia
Day 8
Philipsburg, St. Maarten
ALL DATES &
FARES
7-for-7
Complimentary All-Inclusive Upgrade
Holiday Sailings
Last Minute Cruise Deals
Great cruise-only fares or make it an all-inclusive voyage with unlimited beer, wine, and cocktails, Wi-Fi, and gratuities. From $89 per guest per day.
Every Thursday, enjoy new deals on amazing voyages — valid for 7 days or until sold out! Not combinable with other promotions.
Terms & Conditions
apply.
Book a cruise sailing through March 2025 before November 17, 2024 and you'll receive a complimentary upgrade to our All-Inclusive Fare with Wi-Fi, unlimited alcohol and all gratuities.
A Windstar cruise is always a special occasion, but join us at Thanksgiving, Christmas, Hanukkah, or New Year’s and you’ll find us at our festive best.
Our lowest fares for cruises departing soon! Pack your bags NOW!
Date
Ship
All-Inclusive
From
Cruise Only
From
Sat
Dec 21
2024
WIND SURF
$3,181
$2,558
VIEW
SAILING
Sat
Jan 4
2025
WIND SURF
$3,182
$2,559
VIEW
SAILING
Sat
Jan 18
2025
WIND SURF
$3,342
$2,719
VIEW
SAILING
Sat
Feb 8
2025
WIND SURF
$3,199
$3,199
VIEW
SAILING
Sat
Feb 22
2025
WIND SURF
$3,399
$3,399
VIEW
SAILING
Sat
Mar 15
2025
WIND SURF
$3,199
$3,199
VIEW
SAILING
Sun
Dec 7
2025
WIND SURF
$2,922
$2,299
VIEW
SAILING
Sun
Dec 21
2025
WIND SURF
$3,322
$2,699
VIEW
SAILING
Sat
Feb 7
2026
WIND SPIRIT
Call For Availability
VIEW
SAILING
Sat
Feb 28
2026
WIND SURF
$3,122
$2,499
VIEW
SAILING
Sat
Mar 21
2026
WIND SURF
$2,922
$2,299
VIEW
SAILING
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