Barefoot Break in the British Virgin Islands
 
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Tue Dec 2, 2025 - Sun Dec 7, 2025,
 5 days
 on Wind Surf
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Starting from $2,099 USD
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Philipsburg, St. Maarten to Philipsburg, St. Maarten
The British Virgin Islands is known as the yachting capital of the Caribbean and this five-day escape shows you why. Come with us to charming islands with a laid-back attitude, places where you can still find incredible natural beauty, and colonial towns that effortlessly blend Dutch, French, and Caribbean cultures. Explore 17th century forts and duty-free shopping on St. Maarten and St. Bart. Go snorkeling or take a Jeep off-roading on mountainous Tortola. Visit the Baths on Virgin Gorda – a series of granite boulders sculpted by the sea into incredible natural pools and grottoes. And spend the night on Jost Van Dyke, enjoying the island long after the day-trippers leave – your own private paradise with postcard-pretty crescent beaches, quirky beach bars, and the famous effervescent sea water of the Bubbly Pool.
voyage map
Popular Highlights
Beach Party
Indulge yourself at Windstar's Signature Beach Party with plenty of Caribbean flavors and spirit to savor and share
Jost Van Dyke - overnight
Overnight in Jost Van Dyke with time to snorkel among the sponges and angelfish in Sandy Spit
St. Barts
Get to know the flavor and personality of St. Bart with a late night stay.
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Tue Dec 2
Philipsburg, St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Wed Dec 3
Soper's Hole
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Dec 3
Jost Van Dyke, Great Harbour
Arrive:  7:00 PM
Depart:  
Watersports Platform: 
Thu Dec 4
Jost Van Dyke, Great Harbour
Arrive:  
Depart:  10:00 PM
Watersports Platform: 
Fri Dec 5
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sat Dec 6
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sun Dec 7
Philipsburg, St. Maarten
Arrive:  6:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar) 
? Call for Availability
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
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
Tue, Dec 2 - Sun, Dec 7, 2025
WIND SURF
$2,594
$2,099
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