 At the 2000 World Travel Awards, he was voted "Travel Man of the Millennium" for his work in promoting Caribbean tourism.In 2011, The Caribbean American Foundation presented Stewart with the Golden Eagle Humanitarian Award in recognition of his philanthropic contributions to education and entrepreneurship in the Caribbean.In 2014 Stewart was honored with the Most Innovative All-Inclusive Resort Executive by the Travalliance Travvy Awards, Hotelier of the Year at the Cacique Award held by the Bahamas Ministry of Tourism and Aviation and the Invest Caribbean Now Leadership Award presented at its global summit.