Philipsburg
Photo: Enfoque Samana · Re-encoded to WebP.
Windstar Cruises
Beach Fun & Sun: A Remote Caribbean Getaway
Caribbean
Sailing Itinerary
Trip Details
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Your Ship
Wind Surf
Five masts, seven computer-driven sails, and a hull that spent eight years as Club Med 1
Aboard
- Five masts carrying seven self-furling triangular sails, roughly 26,000 square feet of them
- Built at Le Havre in 1989 as La Fayette and renamed Club Med 1 that January
- Bought by Windstar in 1998; her sister Club Med 2 still sails for Club Med
- Diesel-electric underneath, with four generating sets driving two electric motors
- Phase one of the Setting Sails refit landed in early 2025; the staterooms follow in December 2026
- Caribbean winters from Philipsburg, Mediterranean summers, and the crossings in between
Ashore
Where You Stop
Philipsburg
Caribbean
The Caribbean
The most-sailed water on earth, and the easiest cruise to fall in love with, short flights, warm water twelve months a year, and a different island every morning.
- Best Time to Go
- December through April, outside hurricane season
- Typical Length
- 5 to 8 nights
Compare Dates
The Same Trip, Other Weeks
The identical itinerary on this ship, priced by departure. Fares move week to week, and the difference is often larger than anything else on this page.
| Departs | Inside | Oceanview | Balcony | Suite | From |
|---|---|---|---|---|---|
| December 19, 2026 | |||||
| January 2, 2027This sailing | |||||
| January 16, 2027 | |||||
| January 30, 2027 | |||||
| February 13, 2027 | |||||
| February 27, 2027 | |||||
| March 13, 2027 |
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