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

Photo: FaceMePLS · CC BY 2.0 · Re-encoded to WebP.

Sailing Itinerary

Pricing

Per person, starting from

Book This Cruise

An advisor confirms everything with you.

Trip Details

Departs: January 23, 2028

Returns: January 30, 2028

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.

Compare dates ↓

6 cruises leaving the same week

Other ships and other routes of about this length, from ports near this one.

See alternatives ↓

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.

Call 213-998-7123Ask About This Cruise

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

Compare Alternatives

Sailing the Same Week

Other vacations of about the same length leaving within a few days of January 23, 2028, nearest departure ports first.

Seabourn • 7 Nights

7-Day Yachtsman's Caribbean

Seabourn Ovation

Jan 22, 2028 • departs Philipsburg

From

Norwegian Cruise Line • 7 Nights

7-Day Caribbean Round-trip Orlando (Port Canaveral): Great Stirrup Cay & Cozumel

Norwegian Aqua

Jan 23, 2028 • departs Orlando (Port Canaveral)

From

Royal Caribbean International • 7 Nights

Western Caribbean Cruise

Brilliance of the Seas

Jan 23, 2028 • departs Tampa

From

Celebrity Cruises • 6 Nights

Cayman, Mexico & Bahamas

Celebrity Beyond

Jan 23, 2028 • departs Fort Lauderdale

From

Royal Caribbean International • 7 Nights

Perfect Day CocoCay & Caribbean Cruise

Allure of the Seas

Jan 23, 2028 • departs Miami

From

Carnival • 7 Nights

7-Night Caribbean

Carnival Celebration

Jan 23, 2028 • departs Miami

From