The Wind Knows the Way

Go where the wind takes you and experience the romance, tradition and modern comforts of sailing aboard our three classic Wind Class yachts. Wind is more than a name. It fills our iconic sails and powers us forward to unimaginable and seemingly unreachable places. From the newly renovated Wind Surf, the world’s largest sailing vessel carrying up to 342 guests, to the Wind Star and Wind Spirit carrying just 148 guests, each is perfectly sized to pull into secret lagoons and dock at secluded beaches. Each represents a refreshingly different way to cruise. Stretch out in gracious ocean view staterooms, stroll the polished teak decks and watch for admiring glances as your yacht glides into one magnificent port after another with tall white sails announcing your arrival.

The way to service from the heart. We call them Windstar moments and they’re created by a crew that considers hospitality a calling, not just a job. While you are not a number, our 1.5 to 1 guest-to-crew ratio make acts of personalized attention and recognition a daily occurrence. Simple gestures like remembering your name or recommending a favorite, must-see location ashore isn’t just what we do. It’s how we share our joy of cruising.

Beach Fun & Sun: A Remote Caribbean Getaway

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.

7-day Roundtrip from Philipsburg, St. Maarten
March 14 - 21, 2026

Sat Mar 14 - Philipsburg, St. Maarten

1:00 PM - Embark


Sun Mar 15 - Falmouth Harbour

8:00 AM Arrival - 6:00 PM Departure


Mon Mar 16 - Road Bay

8:00 AM Arrival - 6:00 PM Departure


Tue Mar 17 - Soper's Hole

8:00 AM Arrival - 6:00 PM Departure


Tue Mar 17 - Jost Van Dyke, Great Harbour

7:00 PM Arrival


Wed Mar 18 - Jost Van Dyke, Great Harbour

10:00 PM Departure


Thu Mar 19 - Virgin Gorda / Prickly Pear, British Virgin Islands

8:00 AM Arrival - 5:00 PM Departure


Fri Mar 20 - Gustavia

8:00 AM Arrival - 10:00 PM Departure


Sat Mar 21 - Philipsburg, St. Maarten

6:00 AM - Disembark


BONUS OFFERS:

  • Music provided by Jerry Diaz and Donny Brewer
  • $100 Onboard Credit
  • WindStar Destination Discovery Event