Welcome Aboard!
Starting at $2,325 per person/double occupancy

Price Includes:

  • Taxes and Fees
  • Pre or Post Night package with transfer to ship
  • Welcome Cocktail
  • Open Bridge 
  • Watersports Platform
  • Water Sports Equipment
  • Fine Dining
  • All Non-Alcoholic Beverages
    • Coffee Shops, and other specialty non-alcoholic drinks
  • 7 Ports of Call
  • Port Tenders
  • Entertainment
  • Fitness Center/Classes
  • Destination Briefing


Flights to/from St. Maarten

The Cruise: St. Maarten to St. Maarten

Smaller Ship / Smaller Ports

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.

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. 

Wind Surf
Windstar's Flagship Sailing Ship

On any day, our 342-guest flagship, Wind Surf, the world’s largest sailing ship, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. During their cruise, you will find the perfect setting for ‘making an entrance’ in the beautiful reception area – and, appropriately, that’s only the beginning.

When you return to your stateroom, the luxury gets personal. Windstar’s signature bowls of flowers and fresh fruit will still be waiting for you, along with rich tufted headboards, soft seascape colors, beautiful new upholstery, and fine count Egyptian cotton linens welcome you to an oasis of relaxing indulgence.

Wind Surf underwent a significant renovation of public spaces and suites, including an expanded lounge with new lights and sound for upcoming stage performances. Relax into the destinations you’re visiting at the new World Spa by Windstar, which will offer regional spa treatments, including massage styles like Swedish, Japanese Shiatsu and Hawaiian Lomi Lomi. An Officer’s Suite, which might be the only one of its kind, provides you with the chance to stay in the heart of the officer quarters tucked right behind the Bridge.

Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.

Pre or Post Night at Oyster Bay Beach Resort Included
Discover the “Pearl of the Caribbean”

You’ll be pampered perfectly with ocean views, white sand beach and amenities galore. Located on St. Maarten just south of the amicable French/Dutch divide, you’ll find adventure, serenity, and your life’s dreams come true at this exotic, tropical island resort.