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BAREFOOT BREAK IN THE BRITISH VIRGIN ISLANDS on Wind Surf

Cruise, Ocean cruise, Small Ship/Yacht
Wind Surf at Sea
Exterior view of Wind Surf
Photo Credit: Roger Paperno
  • Exterior view of Wind Surf - Photo Credit: Roger Paperno
  • Captain's Bridge
  • Deck
  • Pool Bar
  • Lounge
  • PoolArea
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.
About Wind Surf
About Windstar Cruises
Windstar Cruises logo

THE WORLD'S BEST SMALL SHIP CRUISE LINE

All cruise ships let you see the world. Only Windstar’s private yacht style cruises brings you close enough so you can truly experience it. Each of our Windstar Cruises yachts serves between 148 and 342 guests. This intimacy provides you with the luxuries of time, space, and freedom to immerse yourself in both the journey and the destination — in ways you may never have imagined possible.

Dec 02, 2025 through
Dec 07, 2025
Nov 26, 2025 7:00 PM
5 Nights from
$2,399.00 (USD)
Per Person
+ $51.00 taxes/fees
Category b

Itinerary

Day Port Arrive Depart
1 Philipsburg, St. Maarten 7:00 PM
2 Jost Van Dyke, Great Harbour 7:00 PM
2 Soper's Hole 8:00 AM 6:00 PM
3 Jost Van Dyke, Great Harbour 10:00 PM
4 Virgin Gorda / Prickly Pear, British Virgin Islands 8:00 AM 5:00 PM
5 Gustavia 8:00 AM 10:00 PM
6 Philipsburg, St. Maarten 6:00 AM
Prices are per-person based on double occupancy, unless otherwise noted.