After completing his education in England, In April 1981, Stewart bought two derelict hotels, the Bay Roc and the Carlisle in
Montego Bay. The Bay Roc had been abandoned for more than five years when Stewart hired architect Evan Williams to renovate the hotel for $4 million and reopen it the same year as the Sandals Resort Beach Club, later known as Sandals Montego Bay. Stewart founded
Sandals Resorts. Stewart is credited with several innovations in the hospitality industry, most notably building the Caribbean's first swim-up bar at Sandals Montego Bay Resort in Jamaica in 1984. In 1985, Stewart opened his second hotel as the Sandals Carlisle which was followed the next year by Sandals Royal Caribbean, “the only resort in Jamaica with its own private island". Over the next few years, Stewart expanded Sandals Resort to
Negril in 1988 and to
Ocho Rios in 1989. In 1991, he opened a second resort in Ocho Rios near the
Dunn's River Falls and also opened Sandals
Antigua, his first resort outside Jamaica. He added two more resorts to the Sandals chain in
Saint Lucia, Sandals La Toc and Sandals Halcyon Beach, which opened in 1993. Sandals Royal Bahamian in
Nassau opened in 1996 and, in 1997, Stewart started a second resort chain geared towards children and families with the opening of a
Beaches Resort in
Providenciales,
Turks and Caicos Islands. and, in 1994, started the Air Jamaica Acquisition Group to buy a majority stake in
Air Jamaica. The group paid $37.5 million for a majority share of the airline; of which, Stewart held a 46 percent stake and became the new chairman of Air Jamaica. Stewart's group sold their shares of the airline back to the Jamaican Government in 2004. In November 2006, Stewart became chairman of Sandals and Beaches Resorts after appointing his son
Adam Stewart as CEO. In 2012, Stewart founded Sandals Corporate University, an adult education program for Caribbean nationals employed by Sandals Resorts, Beaches Resorts and Grand Pineapple Beach Resorts, provided in partnership by Canada-based
Ryerson University, Western Hospitality Institute of Jamaica, and the Jamaica Foundation for Life Long Learning. As of 2012, Stewart’s businesses employed more than 10,000 people in the Caribbean across various industries including hospitality, restaurant, automotive, retail, and media. ==Personal life==