A large white sailing cruise ship with multiple tall masts and billowing sails traveling across calm blue water under a clear sky, with a tree-lined shoreline in the background.

Windstar Cruises

Classic Caribbean

Caribbean

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Sailing Itinerary

Pricing

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Trip Details

Departs: November 28, 2027

Returns: December 5, 2027

Departure Port: Philipsburg

Ship: Wind Surf

Before You Decide

7 other departures of this route

The identical itinerary, priced week by week. The gap is often hundreds of dollars.

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6 cruises leaving the same week

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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
More About Wind Surf

Ashore

Where You Stop

Philipsburg

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
Read the Full Guide
Aerial shot of a tropical beach with a pier, turquoise waters, and a resort in Cozumel.

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.

DepartsFrom
November 28, 2027This sailing
December 12, 2027
December 27, 2027
January 9, 2028
January 23, 2028
February 6, 2028
February 20, 2028
March 5, 2028

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