Initially selling seats on Virgin Atlantic routes to New York City, Miami and Orlando the company has grown to become one of the largest and most successful long-haul scheduled tour operators in the UK.

[2] On 18 December 2008 Virgin Holidays acquired the assets and brand name of Travel City Direct from XL Leisure Group, which collapsed in September 2008.

Nearly a year later, on 15 December 2009, Virgin Holidays announced that it had bought the small independent tour operator, Bales Worldwide.

In November 2019, Virgin Holidays established Orville Richard Burrell (Shaggy) as their Chief Caribbean Officer.

The company name was officially changed to Virgin Holidays Cruises Limited on 15 June 2009.