Philipsburg
Photo: Enfoque Samana · Re-encoded to WebP.
Windstar Cruises
Star Collector: Caribbean Explorations
Caribbean
Sailing Itinerary
Trip Details
Speak With A Specialist
Ready to Book?
Our travel experts are standing by to help plan the perfect getaway. Call us, or send a note and we will come back to you.
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
St. Johns
Basseterre
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 |
|---|---|---|---|---|---|
| November 20, 2027 | |||||
| December 12, 2027This sailing | |||||
| December 19, 2027 |
Compare Alternatives
Sailing the Same Week
Other vacations of about the same length leaving within a few days of December 12, 2027, nearest departure ports first.
Princess Cruises • 15 Nights
Eastern/Western Caribbean with Celebration Key Holiday
Regal Princess
Dec 12, 2027 • departs Miami
From
Princess Cruises • 14 Nights
Southern Caribbean Adventurer Holiday
Emerald Princess
Dec 12, 2027 • departs San Juan
From
Princess Cruises • 14 Nights
Eastern/Western Caribbean Adventurer Holiday
Sky Princess
Dec 12, 2027 • departs Ft. Lauderdale
From
MSC Cruises • 14 Nights
14-Night Caribbean & Bahamas from Miami
MSC Seashore
Dec 12, 2027 • departs Miami
From
Costa Cruises • 14 Nights
Caribbean & Antilles from La Romana
Costa Fascinosa
Dec 12, 2027 • departs La Romana
From
MSC Cruises • 13 Nights
13-Night Eastern & Western Caribbean from Miami
MSC World America
Dec 11, 2027 • departs Miami
From