 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.