• Wind Surf
  • 15 days
  • Philipsburg to Philipsburg
departure date
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Grand Caribbean Holiday

  • Wind Surf
  • 15 days
  • Philipsburg to Philipsburg
select departure date:

Philipsburg to Philipsburg

Caribbean Cruise Map

Here’s a unique way to spend the holidays that will leave you with delightful memories and a stress-free holiday break. The Grand Caribbean Holiday cruise will take you round trip from St. Maarten to 11 unique islands over the course of 16 days. From the stunning UNESCO site of the twin Pitons to the quaint island charm of Soper’s Hole and Roseau. From the dazzling white sand beaches to the mesmerizing waters in shades of peacocks and mermaids, this holiday vacation will leave you equally at home in exotic harbors and hidden coves. Relaxed, relieved, refreshed, you’ve just found a new way to celebrate the season.

TODAY'S FARES: Starting at $5,799 pp
Star Perks Event

Two Local Complimentary Windstar Destination Discovery Events

St. Lucia & Prickly Pear Beach (Virgin Gorda) Island Experiences

Prickly Pear Beach: Island Experience (Virgin Gorda)

You're invited to a private beach party – complete with sun, sand, entertainment, activities – and incredible food and drink. During this event, for invited Windstar guests only, you'll be transported to lovely Prickly Pear Beach – an uninhabited nature refuge with a beautiful white-sand beach and turquoise water. The fun begins when you are greeted by crew members with coconut drinks. Our amazing beach buffet here is worth working up an appetite for — and there are plenty of activities to make that happen. Swim, snorkel, play volleyball or sneak away to relax under an umbrella. Eat and drink to your heart’s content.  The day is yours to choose exactly what you want to do.

St. Lucia : Island Experience (Pigeon Island, St. Lucia)

Be prepared for fun, food, and adventure on this exclusive Windstar Destination Discovery Event. Tender in to a secluded beach at beautiful Pigeon Island, where the bar is open and local calypso music is enticing you to dance.  Coconut drinks welcome you, and while the chefs work their magic, we’ll help you find the fun. Highlights include an Officer vs. Guest volleyball tournament, bocce ball, Steiner Fitness Program, and a mixology class featuring a local-themed drink. We definitely suggest you take advantage of our snorkeling equipment here.  And sample everything you can at the delicious beach buffet. All in all, a special day where, at this Windstar Destination Discovery Event, you can choose to do a lot or nothing at all.

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