By 2004, Sunwing Vacations had become the second largest tour operator in the Ontario area. That year, a former Skyservice employee named Mark Williams approached the CEO of Sunwing Travel Group, Colin Hunter, and asked if he wanted to start an airline. A few weeks later official plans to launch the airline were in place. In November 2005, a Boeing 737-800 departing from Toronto was the airline's inaugural flight. In December 2005, Sunwing flew its first direct flight from Sudbury, Ontario to Varadero, Cuba, making it one the first international flights directly from the Sudbury Airport. In November 2006, the company flew its first flight out of Montreal. By 2008, Sunwing Airlines had grown to operate in 29 cities. of Sunwing Airlines at Bristol Airport, England In 2015, it was announced that Sunwing had finalised a $350 million deal to acquire two Boeing 737-800 and four Boeing 737 MAX 8 aircraft from Air Lease Corporation. The aircraft are due to be delivered over a four-year period from early 2016. Seneca College and the University of Waterloo launched a partnership with Sunwing in 2016 to form a cadet program which includes flight training and mentoring through Sunwing. Sunwing joined the Transportation Security Administration's expedited screening program, TSA PreCheck, in January 2017. At that time, the TSA PreCheck program was available at 180 United States airports and works with 30 airlines. Sunwing took delivery of their first Boeing 737 MAX 8 on May 25, 2018.
Destinations
Sunwing Airlines flies to a wide range of vacation destinations across the Caribbean, Mexico, Cuba, Central and South America. The most popular destinations include Varadero, Punta Cana, Cancun and Montego Bay. Its parent company, the Sunwing Travel Group, is Cuba's largest travel provider internationally, sending over 700,000 vacationers to the destination each year. In Canada, the airline operates several domestic routes, including Toronto to Vancouver which operated daily as of Summer 2015, as well as maintaining year-round service to its most popular destinations. Other connections include Deer Lake, Gander and St John's from Toronto. As of Summer 2015, the airline operated service to Caribbean destinations from Atlanta, Baltimore, Charlotte, Cincinnati, Columbus, Houston, Lansing, Milwaukee, Nashville, New Orleans, Newark, Philadelphia, Pittsburgh and Rockford. In summer, Sunwing Airlines sends many of their 737-800 aircraft over to Europe to operate for the TUI Group during their extremely busy season. The aircraft operate flights all around Europe for the company. Sunwing has an agreement with ULCC Swoop that allows passengers out of Hamilton, London, Edmonton, Abbotsford, and Winnipeg to book Sunwing vacation packages with Swoop flights.
Fleet
The Sunwing Airlines fleet consists of the following aircraft as of 2019:
