Get to Know Wind Surf
Windstar's Flagship Sailing Yacht
As part of our Wind Class, our 342-guest Wind Surf offers a sailing experience like no other — one with real working sails
Newly upgraded under our Setting Sails initiative, Wind Surf features redesigned common areas that include our lounge, the pool deck and bar, the Yacht Club Café, a newly minted wine room and much more.
Our flagship sailing yacht features stylish staterooms and multiple suites, including opulent Bridge Suites, an Officer’s Suite, and brand-new versions of the Broadmoor and Sea Island Suites currently on our Star Class yachts.
And did we mention all dining is included? From gourmet bites at our Yacht Club Café to specialty restaurants like Stella Bistro, our award-winning cuisine is always complimentary, so you can indulge freely.
Ready to experience Wind Surf for yourself? Join us on one of her voyages in the Caribbean and Mediterranean — and get ready to sail 180 Degrees From Ordinary©.
Begin your cruise in Philipsburg, St. Maarten.
- 3/20/2027 13:00 – Embark Philipsburg, St. Maarten
- 3/20/2027 19:00 – Departure Philipsburg, St. Maarten
Board Wind Surf, get settled into your stateroom or suite, explore the ship, and sail out of Philipsburg in the evening to start your Classic Caribbean itinerary.
Port call in Charlestown
Enjoy a full day in Charlestown as part of your Classic Caribbean itinerary.
- 3/21/2027 08:00 – Arrival Charlestown
- 3/21/2027 17:00 – Departure Charlestown
Go ashore to explore Charlestown or join optional shore excursions before returning to Wind Surf for evening departure.
Port call in Roseau, Dominica
Spend the day in Roseau, Dominica.
- 3/22/2027 08:00 – Arrival Roseau, Dominica
- 3/22/2027 16:00 – Departure Roseau, Dominica
Disembark to discover Dominica’s capital or join optional shore excursions, then reboard Wind Surf for afternoon departure.
Port call in Mayreau
Visit the small island of Mayreau on your Classic Caribbean cruise.
- 3/23/2027 08:00 – Arrival Mayreau
- 3/23/2027 17:00 – Departure Mayreau
Enjoy beaches, swimming, or optional watersports and excursions before the ship departs in the late afternoon.
Port call in Les Saintes, Guadeloupe
Explore Les Saintes, Guadeloupe with an afternoon and evening visit.
- 3/24/2027 12:00 – Arrival Les Saintes, Guadeloupe
- 3/24/2027 18:00 – Departure Les Saintes, Guadeloupe
Spend the afternoon discovering this charming archipelago before reboarding Wind Surf for evening departure.
Port call in Basseterre, St. Kitts
Enjoy a long day in Basseterre, St. Kitts.
- 3/25/2027 08:00 – Arrival Basseterre, St. Kitts
- 3/25/2027 22:00 – Departure Basseterre, St. Kitts
Take advantage of the extended stay to explore Basseterre and the island of St. Kitts or join optional tours and activities
Port call in Gustavia, St. Barthelemy
Visit Gustavia, St. Barthelemy (St. Barts) for a full day and evening.
- 3/26/2027 08:00 – Arrival Gustavia, St. Barthelemy
- 3/26/2027 22:00 – Departure Gustavia, St. Barthelemy
Explore Gustavia’s harbor town, beaches, boutiques, and cafes or join optional excursions before sailing late in the evening.
Disembarkation in Philipsburg, St. Maarten
Return to Philipsburg, St. Maarten to conclude your Classic Caribbean cruise.
- 3/27/2027 06:00 – Arrival Philipsburg, St. Maarten
- 3/27/2027 07:00 – Disembark Philipsburg, St. Maarten
After early morning arrival, disembark Wind Surf in Philipsburg and continue with your onward travel plans.
