Adam Stewart was in elementary school when he started stuffing envelopes in a Sandals’ mailroom. Today, at 31, he is the CEO of the company his father launched shortly after Stewart was born. The Sandals Resorts empire has grown from one hotel to 21 resort properties across five islands in the Caribbean and is the market leader in destination weddings (70,000 couples a year). Stewart’s work requires him to leave his home base of Jamaica to travel throughout the Caribbean four to five times a week.
When was your first business trip?
I was 13 years old, and it was the first year Sandals won [World’s Leading Independent Resort] at the World Travel Awards. There was a big function in New York. I’ll never forget it; I had to buy my first tuxedo. I went to Barneys—it was the only place open nearby. I had a red bow tie. Until then, I’d never worn a tuxedo in my life.
What are three things you can’t leave home without?
All three of my phones. I never leave home without my passport, my BlackBerry and my American Express card.
Any packing tips?
No matter how much I travel, I always forget something—socks, my belt, underwear or something. I don’t think I’ve ever been on a trip and not forgotten at least one item. When my wife packs for me, I have everything. So my tip is: find a good wife and let her pack for you!
Any travel advice?
I take a lot of vitamin C, Airborne particularly, and I constantly wash my hands. There are always germs around and you always end up being sick when you travel a lot. I try to pack light. You need to think through what you’re going to do, otherwise you carry around a small army of suitcases with you.
Favourite travel destination—other than a Sandals resort?
I love England—my mom is British. I love the fresh fruit and driving in the countryside. You’re always on call in the hotel industry, so to go to the UK puts me on a totally different time schedule, which means I can truly rest because I know people are sleeping when I’m awake.
Most memorable travel experience?
I went on a trip to South Africa four years ago. That trip was just magic for me. I went on a safari where the days were full of huge skies and non-stop land. At night, it would rain and the thunder would come rolling across hundreds of thousands of acres. It was beautiful. I’ve spent a lot of time on small islands. So, for me, going inland and seeing the wild animals and the big sky in Africa was really, really unique.
Stewart’s love of cars drove him to open up ATL Automotive in Jamaica in 2010. Two of his favourites?
His Land Rover Defender 90 soft-top convertible
“I take it to the backcountry of Jamaica—to the rivers and the mountains.’’
His dream car
Aston Martin DBS. ‘‘Everyone says I named my son after Aston Martin.”’