First in Service News

Agent Spotlight: Gary Oakley

italy2Like many of his colleagues, Gary Oakley was born into a family of global travelers. But Gary, who runs our new Miami office, is the only one who can call himself a Jamaican-born, London-raised Miamian.

Even after 15 years in Miami, Gary occasionally slips in a hint of British accent, especially when he’s excited about something. Quite often that involves talking about his passion for travel and the industry.

“My upbringing definitely help mold my life and career choices,” he explains. “Being born in the Islands gave me a love of nature, adventure and the ability to dream big. My father was a photographer and later worked for an airline, so we’d travel a lot. When we moved to England, Dad really opened up my eyes to appreciate history, fashion and cultural diversity.”

At 15, Gary moved to Miami. He thought he wanted to become a pilot, so he could travel. His first job after school was with Air Jamaica as a ticketing agent. He fell in love with the travel industry and quickly realized he had other options in the industry. His career took off, working for airlines, luxury cruise operators, and travel management companies. Over time, he developed a niche clientele in the entertainment industry – from movie stars to club owners.

When he heard that First in Service was opening a Miami office, the deal to come onboard was sealed.

Gary’s pride in his city is infectious. He’s quick to point out the best in food, culture, and entertainment. He also loves the melting pot of so many cultures – Latin, Jamaican, Russian, Eastern European, and Haitian. A perfect weekend for him would involve hotel hopping (“The 1 Hotel is my fave!”) for lunch and drinks and hitting Brickell or Wynnwood for dinner.

Food has always been a big part of his life. “If I’m not cooking my mean Jamaican-style chicken curry, you’ll find me at Drunken Dragon, for super authentic Japanese BBQ, hidden behind an unmarked door. I also love Quality Meat for amazing seafood and meat.”

The father of two teenage daughters, he’s excited to have passed on his passion for food and travel. He adds, “We love being active whenever we’re together. Whether that’s cooking at home, going out, or taking trips to Jamaica, New York, or California.”

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