The Caribbean Cup Tennis Series team is made up of people of different ages, backgrounds and ethnicities. We are all passionate about tennis and people, all working together to make your tennis experience exceptional. We pride ourselves on seamlessly merging tennis and travel by planning your tennis events throughout the Caribbean. Check out below the pretty faces that bring your event to life.
Karl Hale has an accomplished tennis history. He has played competitive tennis internationally, participated as a player and coach in Davis Cup for Jamaica, and is a former Fed Cup coach for Canada. He was named tournament director of Rogers Cup presented by National Bank in Toronto on December 11, 2006.
Hale was born in Falmouth, Jamaica and played Davis Cup tennis from 1988 to 1999 and again in 2004. He held the Davis Cup record for longest three-set match, winning 23-21 in the final set. In 2003, Hale was coach of the Canadian Fed Cup team that advanced to a World Group play-off tie against Austria. He later returned to his native Jamaica to coach the Davis Cup team in 2005.
Hale was named the Rogers Cup Tournament Director in November of 2006. Hale’s relationships with the players, and sports and entertainment celebrities have helped raise the profile of this world-class tennis event. Karl was also vice-president of the PTR (the largest tennis coaching organization in the world with over 20,000 members) in 2017/18.
Most importantly, Hale is a passionate supporter of children’s charities. Hale is well-known and respected for his tremendous philanthropic work. He founded the Helping Hands Jamaica Foundation, which has raised over $2,000,000 for education in his native Jamaica and built 18 kindergarten schools (including one with Serena Williams). He also developed the Daniel Nestor Celebrity Charity event, which raised more than $1,000,000 in support of the Go for Gold Olympic program and North York General Hospital. He has spent tennis time overseas, coaching in Tokyo for five years, teaching adults and juniors at the prestigious Kashiwa Lawn Tennis Club. He worked with several top players and his juniors have received over $1,000,000 in tennis scholarships.
Jolande is one of our tour managers and has a background in sports management and graphic design. She is a former elite Volleyball player and has worked with numerous other National and International sport organizations. She also travels with us as a tour manager, ensuring our guests have the best experience possible!
Our other tour manager, Alex, played college tennis in Florida before returning to Canada to work in finance and technology for most of his professional career. His strength on the tour is in IT, and is one of the most likeable people you will ever meet.
Sports administrator asst.
Jaimi is a third year undergraduate student, studying international relations at the University of Toronto. Originally from Arizona, Jaimi was drawn to Toronto because of its incredibly diversity and opportunity to meet people from around the world. Jaimi has always been passionate about sports, and currently plays on the University of Toronto Varsity Tennis team. Following graduation, she hopes to use her background in hospitality and marketing to pursue her dream of working in the Sports and Entertainment industry, and become an event planner.