History Prior to 1988
The line was established as Windstar Sail Cruises in 1984, and its first ship, the msy Wind Star, launched in 1986, followed by the Wind Song and Wind Spirit. Two additional ships were ordered from the French "Ateliers et chantiers du Havre" shipyard: the Wind Surf and the Wind Saga. These two ships were to be larger than the originals, holding over twice the amount of passengers and reaching a length of 660 ft compared to the smaller vessels of 440 ft in length.
Purchase by Holland America Line
Holland America Line purchased 50% of Windstar Sail Cruises in 1987 and purchased the balance of the company in 1988. HAL became a subsidiary of Carnival Corporation & plc in 1989. The option to continue building the Wind Surf and the Wind Saga was passed up by HAL. With assistance from the French Government the two larger ships were built for Club Med as Club Med I and Club Med II, with HAL / Carnival retaining rights of first refusal for purchase.
In 1998, Windstar acquired the sail cruiser Club Med I from Club Med Cruises, and rechristened her to her original name Wind Surf.
In 2002, the Wind Song was damaged by an engine room fire in Tahiti causing great damage to the vessel. Subsequently classed as a total loss, with permission of the Tahitian Government the ship was cleaned and later scuttled in Tahitian waters between Moorea and Tahiti in approximately 3,000 meters of water.
In the summer months the Windstar fleet sails the Mediterranean shores and in the Winter months the company sails the Caribbean and the Pacific coast of Costa Rica.
Windstar is considered a high-end cruise line, with its ships typically getting a four-star (out of five) rating. The ships are relatively small, with the Wind Surf having a capacity for about 300 passengers, and the others about 150.
The ships are registered in the Bahamas. Under this flag they are some of the few cruise ships in the world where passengers are still allowed on the bridge (though not when entering or leaving port). Given their small size the service is very personal, and interaction with the ship's officers is easy. With a shallow draft of only 14' the ships can enter ports that are inaccessible to larger cruise liners. In some cases passengers need to take smaller boats into port (such as to Lipari) when the ship is at anchor, but access on and off a shipboard ramp is easily made.
Sale of Windstar to Ambassadors International
On April 1 2011, Windstar's parent company Ambassadors International filled for Chapter 11 Bankruptcy and Windstar was planned to be sold to a company in White Plains, New York known as Whippoorwill Associates, Inc. But through a Bankruptcy court in Delaware, a two day bid was held and Anschutz Corporation won Windstar Cruises which had the best bid of $39 Million. They in turn sold the company, and Xanterra Parks and Resorts are now the parent company.
It was announced on February 19, 2013 that Windstar completed the purchase of Seabourn Cruise Line's Seabourn Pride, Seabourn Legend, Seabourn Spirit. The Seabourn Pride will enter service in May 2014, sisters Seabourn Legend & Seabourn Spirit will enter service in May 2015 following a dry dock period. 
|msy Wind Star||1986||?||1986 - Present||5,350 tons||Bahamas|
|msy Wind Spirit||1988||?||1988 - Present||5,350 tons||Bahamas|
|msy Wind Surf||1989||?||1998 - Present||14,745 tons||Bahamas||Previously Club Med I.|
|msy Wind Song||1987||?||1987 - 2002||5,350 tons||Bahamas||Ship was lost following an engine room fire in 2002.|
|Gross Tonnage||Planned Flag||Notes|
|Seabourn Pride||1988||Schichau Seebeckwerft||May 2014||10,000 tons||Bahamas||Departing Seabourn fleet in April 2014. |
|Seabourn Spirit||1988||Schichau Seebeckwerft||May 2015||10,000 tons||Bahamas||Departing Seabourn fleet in May 2015 |
|Seabourn Legend||1990||Schichau Seebeckwerft||May 2015||10,000 tons||Bahamas||Departing Seabourn fleet in April 2015 |
- Windstar sold to Ambassadors International