Beach Fun & Sun: A Remote Caribbean Getaway
 
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Sat Mar 7, 2026 - Sat Mar 14, 2026,
 7 days
 on Wind Surf
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Starting from $2,799 USD
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Special Offers And Updates

Go All-Inclusive — On Us

Enjoy complimentary wine, beer and cocktails, Wi-Fi, and gratuities — worth up to $1,350 per couple on a 7-night cruise on cruises departing through March 2026.

Accommodations & Pricing

On any day, our 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. During their cruise, you will find the perfect setting for ‘making an entrance’ in the beautiful reception area – and, appropriately, that’s only the beginning.

When you return to your stateroom, the luxury gets personal. Windstar’s signature bowl of fresh fruit will still be waiting for you, along with rich tufted headboards, soft seascape colors, beautiful new upholstery, and fine count Egyptian cotton linens welcome you to an oasis of relaxing indulgence.

Wind Surf underwent a significant renovation of public spaces and suites, including an expanded lounge with new lights and sound for upcoming stage performances. Relax into the destinations you’re visiting at the new World Spa by Windstar, which will offer regional spa treatments, including massage styles like Swedish, Japanese Shiatsu and Hawaiian Lomi Lomi. An Officer’s Suite, which might be the only one of its kind, provides you with the chance to stay in the heart of the officer quarters tucked right behind the Bridge.

Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.

Windstar has always been known for our iconic sailing ships, and now we are embarking on a multi-year refresh of the Wind Class ships. The initiative, Setting Sails: A Wind Class Refresh, brings the tight-knit connection of the Windstar community to the forefront through the redesign of public spaces and staterooms. From a revamped lobby to a new pool and larger pool bar, new World Spa by Windstar to a redesigned lounge, this initiative also includes intricate details like new teak decks and décor for a timeless and welcoming experience. Wind Surf will complete her redesign in 2026.

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Category B
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Guaranteed Cabin** (chosen by Windstar)
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Category BX Deluxe
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Category A
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Category AX Deluxe
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Category TX Deluxe
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Suite
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Officer's Suite
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Bridge Suite
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Beach Fun & Sun: A Remote Caribbean Getaway
Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
7 days
Day
Port
Day 1
Philipsburg, St. Maarten
Day 2
Falmouth Harbour
Day 3
Road Bay
Day 4
Virgin Gorda / Prickly Pear, British Virgin Islands
Day 4
Soper's Hole
Day 5
Soper's Hole
Day 6
Jost Van Dyke, Great Harbour
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 14
2025
WIND SURF
$2,599
$2,599
Sun
Dec 28
2025
WIND SURF
$3,399
$3,399
Sun
Jan 4
2026
WIND SURF
$2,899
$2,899
Sat
Jan 24
2026
WIND SPIRIT
$2,999
$2,999
Sat
Jan 31
2026
WIND SPIRIT
$2,699
$2,699
Sat
Feb 14
2026
WIND SPIRIT
$2,999
$2,999
Sat
Feb 21
2026
WIND SPIRIT
$2,799
$2,799
Sat
Mar 7
2026
WIND SURF
$2,799
$2,799
Sat
Mar 14
2026
WIND SURF
$2,899
$2,899
Sat
Mar 28
2026
WIND SURF
$2,599
$2,599
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