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MY WINDSTAR
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Beach Fun & Sun: A Remote Caribbean Getaway
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Sat Jan 31, 2026 - Fri Feb 6, 2026,
6 days
on Wind Spirit
Call For Availability
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Beach Fun & Sun: A Remote Caribbean Getaway
Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
6 days
Close
Day
Port
Day 1
Philipsburg, St. Maarten
Day 2
St. John's
Day 3
Road Bay
Day 4
Soper's Hole
Day 4
Jost Van Dyke, Great Harbour
Day 5
Jost Van Dyke, Great Harbour
Day 6
Virgin Gorda / Prickly Pear, British Virgin Islands
Day 7
Gustavia
Day 8
Philipsburg, St. Maarten
ALL DATES &
FARES
Complimentary All-Inclusive Upgrade
Holiday Sailings
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.
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.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sat
Dec 28
2024
WIND SURF
$4,299
$4,299
VIEW
SAILING
Sat
Jan 11
2025
WIND SURF
$3,199
$3,199
VIEW
SAILING
Sat
Jan 25
2025
WIND SURF
$3,399
$3,399
VIEW
SAILING
Sat
Feb 1
2025
WIND SURF
$3,499
$3,499
VIEW
SAILING
Sat
Feb 15
2025
WIND SURF
$3,199
$3,199
VIEW
SAILING
Sat
Mar 1
2025
WIND SURF
$3,399
$3,399
VIEW
SAILING
Sat
Mar 8
2025
WIND SURF
$3,099
$3,099
VIEW
SAILING
Sat
Mar 22
2025
WIND SURF
$3,199
$3,199
VIEW
SAILING
Sun
Dec 14
2025
WIND SURF
$3,022
$2,399
VIEW
SAILING
Sun
Dec 28
2025
WIND SURF
$3,322
$2,699
VIEW
SAILING
Sun
Jan 4
2026
WIND SURF
$3,222
$2,599
VIEW
SAILING
Sat
Jan 24
2026
WIND SPIRIT
$3,222
$2,599
VIEW
SAILING
Sat
Jan 31
2026
WIND SPIRIT
Call For Availability
VIEW
SAILING
Sat
Feb 14
2026
WIND SPIRIT
$3,222
$2,599
VIEW
SAILING
Sat
Feb 21
2026
WIND SPIRIT
$3,222
$2,599
VIEW
SAILING
Sat
Mar 7
2026
WIND SURF
$3,322
$2,699
VIEW
SAILING
Sat
Mar 14
2026
WIND SURF
$3,022
$2,399
VIEW
SAILING
Sat
Mar 28
2026
WIND SURF
$3,022
$2,399
VIEW
SAILING
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