Windstar Caribbean Cruise Travel Guide

Guide to Windstar Cruises in the Caribbean

Windstar Cruises

Windstar Cruises offers distinctive Caribbean cruises "miles from ordinary," as they like to say – on a pair of tall-masted sail/motor yachts that provide a laid-back but upscale cruising experience that includes stops at a number of off-the-beaten-path ports and destinations. And, with new renovations coming in 2015 and 2016, Windstar Cruises continues to expand their luxury service - to the Caribbean, and far beyond.

Basic Information on Windstar Cruises


  • Contact information::Corporate (206)733-2703
    Reservations (800)258-7245
    Guest Relations (206)733-3005
  • Description: Small-ship upscale cruising.
  • Ships: 6
  • Cruise length: 6-15 days
  • Price: $1,649-$3,549 per person


Windstar: Ships Cruising the Caribbean

Windstar operates six ships: the 148-passenger Wind Star and Wind Spirit, the 308-passenger Wind Surf, and the newly christened Star Breeze, Star Pride, and Star Legend. The Wind Star, Wind Spirit, and Wind Surf travel to different destinations throughout the Caribbean and Mediterranean, depending on the set itinerary and number of passengers. The new ships to the line - Star Breeze, Star Pride, and Star Legends - travel to 150 ports in 50 nations throughout Europe, the South Pacific, the Caribbean, and Central America. All of the Windstar Cruise vessels resemble tall ships with their full sails, but can operate on engine power as well as wind. Known for their "casually elegant" atmosphere, the ships feature all ocean-view cabins, bistro-style restaurants, casino, pools, spa (varies per ship), library, and fitness center.

  • Cruise Mates Wind Spirit Review
  • Cruise Mates Wind Surf Review


In 2015, Windstar also announced that 2016 will bring new renovations to the Star Pride, including $3 million's worth of upgrades to the reception, screening room, and more. 

Windstar: Onshore Events 

In 2015, Windstar Cruises announced that every passenger itinerary now includes an onshore private event, including, but not limited to: a 5-star meal at a local eating establishment; an exclusive wine-tasting; after-hours tours of local historical landmarks; dance and music lessons; and more! Onshore events vary per trip. 

Windstar: Caribbean Home Ports

All of Windstar's Caribbean cruises begin and end in St. Thomas, St. Martin, U.S. Virgin Islands, or Bridgetown, Barbados. All can be accessed via direct flights from the continental U.S. or via San Juan, Puerto Rico.


Windstar: Caribbean Ports of Call

Windstar's smaller ships allow the line to get into some smaller ports than fleets operated by the likes of Royal Caribbean and Carnival, such as Pigeon Island in St. Lucia and Iles des Santes in the French West Indies. Windstar's standard ports of call include the French West Indies (St. Martin, St. Barts), U.S. Virgin Islands (St. John, St. Thomas), British Virgin Islands (Tortola, Jost Van Dyke, Virgin Gorda), Barbados, the Bahamas, and Puerto Rico.


Windstar: Caribbean Itineraries

Windstar Cruises offers a variety of trips, including: a 10-day trip to Tahiti and the Tuamoto Islands; a 7-day trip to Puerto Rico and the Panama Canal; and a 10-day Caribbean tour called "Yachtsman's Caribbean," departing from Philipsburg, St. Martin. 

For more itinerary information, check out: 

Book Windstar Cruises with CruiseDirect

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