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.