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Be one of the first to experience Windstar's newest yacht. Inaugural season begins in 2026!
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Beach Fun & Sun: A Remote Caribbean Getaway
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Sat Mar 14, 2026 - Fri Mar 20, 2026,
6 days
on Wind Surf
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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
Falmouth Harbour
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
Holiday Sailings
Last Minute Cruise Deals
Pick Your Perk
Great cruise-only fares or make it an all-inclusive voyage with unlimited beer, wine, and cocktails, Wi-Fi, and gratuities. From $99 per guest per day.
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!
Windstar’s Pick Your Perk offer is back for another season of savings. With options that match your travel style, you get to make the most of your vacation, your way. Reserve a cruise departing through June 2026 and you'll get to choose between an onboard credit, a hotel stay or — for Premium Suite guests — an All-Inclusive package.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sat
Feb 15
2025
WIND SURF
$2,931
$2,238
VIEW
SAILING
Sat
Mar 8
2025
WIND SURF
$2,931
$2,238
VIEW
SAILING
Sat
Mar 22
2025
WIND SURF
$3,411
$2,718
VIEW
SAILING
Sun
Dec 14
2025
WIND SURF
$3,092
$2,399
VIEW
SAILING
Sun
Dec 28
2025
WIND SURF
$3,392
$2,699
VIEW
SAILING
Sun
Jan 4
2026
WIND SURF
$3,292
$2,599
VIEW
SAILING
Sat
Jan 24
2026
WIND SPIRIT
$3,292
$2,599
VIEW
SAILING
Sat
Jan 31
2026
WIND SPIRIT
$3,192
$2,499
VIEW
SAILING
Sat
Feb 14
2026
WIND SPIRIT
$3,292
$2,599
VIEW
SAILING
Sat
Feb 21
2026
WIND SPIRIT
$3,292
$2,599
VIEW
SAILING
Sat
Mar 7
2026
WIND SURF
Call For Availability
VIEW
SAILING
Sat
Mar 14
2026
WIND SURF
Call For Availability
VIEW
SAILING
Sat
Mar 28
2026
WIND SURF
$3,092
$2,399
VIEW
SAILING
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