Beach Fun & Sun: A Remote Caribbean Getaway
 
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Sat Mar 22, 2025 - Fri Mar 28, 2025,
 6 days
 on Wind Surf
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Starting from $2,718 USD
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Philipsburg, St. Maarten to Philipsburg, St. Maarten
Bask on remote beaches resplendent in natural beauty during this relaxing, unrushed, and uncrowded 7-day getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from Windstar’s onboard Watersports Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar takes you to the secret beaches and invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.
 
voyage map
Popular Highlights
Beach Party
Let yourself go – at Windstar’s Signature Beach Party, where the Caribbean spirit is in full swing.
Jost Van Dyke
 Let the Bubbly Pool on Jost Van Dyke wash your cares away.
Normal Island
Relax on the sands of Norman Island, inspiration for Robert Louis Stevenson’s Treasure Island
 
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Sat Mar 22
Philipsburg, St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sun Mar 23
Falmouth Harbour
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Mar 24
Road Bay
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Mar 25
Soper's Hole
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Mar 25
Jost Van Dyke, Great Harbour
Arrive:  7:00 PM
Depart:  
Watersports Platform: 
Wed Mar 26
Jost Van Dyke, Great Harbour
Arrive:  
Depart:  10:00 PM
Watersports Platform: 
Thu Mar 27
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Fri Mar 28
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Mar 29
Philipsburg, St. Maarten
Arrive:  6:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
Category B
Category B
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $2,718 per guest
? All-inclusive price from $3,411 per guest
The Windstar Life
The Windstar staff-to-guest ratio is 1:1.5, and it shows.The moment you board you’ll feel it: an ever-attentive crew at your service, providing you with what you want and need, when you want and need it.
Friendly and Relaxed Atmosphere
Signature Onboard Barbecue
Cooking Demonstrations
ALL DATES &
FARES
Last Minute Cruise Deals
Pick Your Perk
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited select beer, wine, and cocktails, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sat, Mar 22 - Fri, Mar 28, 2025
WIND SURF
$3,411
$2,718
THIS
SAILING
Sun, Dec 14 - Sat, Dec 20, 2025
WIND SURF
$3,092
$2,399
Sun, Dec 28 - Sat, Jan 3, 2026
WIND SURF
$3,592
$2,899
Sun, Jan 4 - Sat, Jan 10, 2026
WIND SURF
$3,292
$2,599
Sat, Jan 24 - Sat, Jan 31, 2026
WIND SPIRIT
$3,292
$2,599
Sat, Jan 31 - Fri, Feb 6, 2026
WIND SPIRIT
$3,192
$2,499
Sat, Feb 14 - Fri, Feb 20, 2026
WIND SPIRIT
$3,292
$2,599
Sat, Feb 21 - Fri, Feb 27, 2026
WIND SPIRIT
$3,292
$2,599
Sat, Mar 7 - Fri, Mar 13, 2026
WIND SURF
Call For Availability
Sat, Mar 14 - Fri, Mar 20, 2026
WIND SURF
Call For Availability
Sat, Mar 28 - Fri, Apr 3, 2026
WIND SURF
$3,092
$2,399