Beach Fun & Sun: A Remote Caribbean Getaway
 
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Sun Dec 28, 2025 - Sun Jan 4, 2026,
 7 days
 on Wind Surf
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Starting from $3,399 USD
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When you book your hotel through Windstar, you get the peace of mind to enjoy and relax your vacation. Not only does Windstar hand-select and curate premium hotels, we offer only preferred category rooms for your comfort. If you’re looking to explore during your stay, all you need to do is stop by Windstar-hosted on-property service desk for insider tips, day trip itineraries, restaurant recommendations, and where to find the best place for viewing the sunset

Oyster Bay Beach Resort

Oyster Bay Beach Resort

Perched on a beautiful coral reef overlooking the Atlantic Ocean, this resort is just south of the French/Dutch divide with spectacular views and gorgeous sunrises. The bright contemporary rooms of the modern resort have balconies with loaner beach umbrellas and snorkeling equipment available.

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
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
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
$2,699
$2,699
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
Click on the date to view the map and itinerary by date