Behind the scenes: How Cayman draws world-class talent

Internationally renowned entertainers and sports figures come to Cayman every year for festivals, tournaments and perhaps most importantly, to foster knowledge and enthusiasm for diverse arts and sports among Cayman’s youth. What does it take to bring about these major events? The Journal talks with a number of organizers to find out.  


For a territory of fewer than 60,000 full-time residents on a scattering of Caribbean islands remote from big population centers, Cayman can boast far more than its share of high-quality sports events and arts performances each year. How do event organizers do it? 

After all, Cayman’s entertainment venues are a long way from London, New York, Paris or Los Angeles, where recording and stage artists like singer Alicia Keys, classical saxophonist Amy Dickson, the Harlem Gospel Choir and Stringfever quartet routinely play and record. Or from Atlanta, where the USA Rugby South club holds its home matches in front of roaring crowds.  

Yet several thousand Cayman residents and island visitors have sat in awe at such international-class talent in concert and leaped to cheer the Cayman Rugby Union in games against USA South and others of the world’s top clubs. 

That’s not all. Music festivals bring in top jazz groups; first-class USA and South African tennis pros teach and oversee matches at the Cayman Islands Tennis Club; swimming and boxing competitions between local and off-island athletes are staged with regularity. 

Rugby is going strong on Cayman, with a big extravaganza planned for mid-June. And visiting dance and music professionals spend time guiding local talent with workshops and master classes almost every time they arrive here for concerts. 

Theo Cuffy, a director of the Cayman Islands Cricket Association, says his popular sport has been importing a treasure trove of top stars from around the world as part of the local clubs’ match and exhibition schedule for years – with no plans to slow down. 

These civic-focused organizations all keep a cosmopolitan tone to the entertainment business in Cayman, in spite of its relative remoteness and smaller-city realities. But there are hindrances that might keep foreign talent from performing here. Historically, one hurdle has been government immigration rules.  

Professional athletes and entertainers don’t just do their jobs for fun. They require paychecks. And in Cayman, anyone who arrives on-island from elsewhere and makes money from a visit must have a work permit.  

For people who work here for months or even years, it’s often not such a big deal. Rob Seward, director of tennis and club manager at the Cayman Islands Tennis Club, has been working as a pro and manager there for nine years, hired from his home in San Diego, California. He’s now seeking permanent residency, but his annual work permits have cost him only about $100 a year.  

Two other tennis pros, both from South Africa, each of whom has been here at least five years, pay a similar filing fee for their permits. In part, the fee is low because the tennis club is structured as a nonprofit institution. The Cayman government has made it easier and less expensive for employees of nonprofits to receive their work permits than those who work for for-profit enterprises, like the scores of financial institutions in Grand Cayman.  

Temporary work permits for entertainers at bars or for conventionally promoted concerts can be more expensive, depending on the pay schedule of the talent and other circumstances.  

Still, professional event promoters say booking popular world talent like Jamaican hip-hop artist Shaggy, who appeared in early March at Margaritaville on the waterfront in George Town, has become easier than in the past. 

“Cayman Island Immigration has now implemented a visitor work visa, or letter of invitation,” Margaritaville’s sales and marketing manager Cedric Gidarisingh said. The booking agent can do all the paperwork at the airport, he said. “The process is very simple. We complete the form, include our business license, a cover letter and $125 USD. We don’t have to go through the long work-permit process at the Immigration office.”  

Margaritaville, part of a chain of clubs that singer-songwriter Jimmy Buffet operates, has no nonprofit tie-in, and the Shaggy booking “was 100 percent funded by Margaritaville,” Gidarisingh said.  

But Cayman Immigration has made it even easier for civic groups not organized as profitable businesses to bring in sports figures and entertainers. And with nonprofit status, in Cayman and elsewhere, come volunteers to help make things happen. 

“It’s true. Behind the scene, dozens of people give their time to make our matches and big rugby weekends a success,” said Richard Adams, CEO of Cayman Rugby Union.  

Echoing his comment is Nadia Hardie, head of marketing for Deloitte Cayman, a regular sponsor of the islands’ cultural scene. 

“It’s great there are so many residents and companies here that support these activities,” Hardie said. The local office of Deloitte, an international accounting and consulting firm, has been a financial and consulting partner with the Cayman Arts Festival, which recently presented award-winning recording star Amy Dickson to the wild approval of audiences here. 


Big-city talent, thanks to nonprofits  

Many big cities are able to provide a greater depth of entertainment options than Cayman because of the intensity of demand that a big population assures. Moreover, professional event promoters say, bands and sporting teams can easily transport their personnel and equipment from major hub to major hub, charging off transportation as a cost of doing business. Getting to Cayman, though, means flying from only a small range of airports in Europe, Latin America, the U.S. and Canada. 

“I’ve looked into it, promoting concerts and stuff in the Cayman Islands,” said Hiram Marquis, a music promoter in Chicago. “But as a private, for-profit business, it’s hard to make the numbers work. The hassle and expense of getting work permits for, say, every member of a rock band, all the roadies and equipment and staging people, it’s just too great a financial burden. You price yourself out of the market.” 

According to Marquis, trying to book off-island talent into more modest Cayman nightclubs that don’t have the resources of, say, Margaritaville (or its international cachet), is similarly difficult economically.  

“So, here’s a place that has all these seasonal visitors and a great local crowd that likes its music and festivals. If their laws, their relatively small market and the cost of travel might discourage promoters like me, they’ve got something that a lot of places don’t – this nonprofit, volunteer-driven entertainment business that involves many of the well-heeled residents and, certainly, the wealthy corporations that have off-shore offices in Cayman,” Marquis said.  

“For those reasons, no way is the Cayman Islands an entertainment backwater.” 

Nisha Bismillah, who, with Pamela McDonough Brown, serves as co-manager of the Cayman Arts Festival, will second that. For a decade, the festival has been one of the choice events for music and dance fans on island, and for hundreds of visitors, too.  

“Every concert has a lovely feel, and all the musicians have said they want to come back, and we have great audience approval,” Bismillah says. 

Beyond that, she says, “We consider the education component our real raison d’etre for our festival. That’s why it’s here. That’s why all of us, as volunteers, are willing to work so hard to make the events come off year after year. 

“These artists bring something so special to our community, doing workshops with local musicians and master classes with the ones who are really refining their musical arts. 

“Amy Dickson came here and stayed with me. She loved the island, as almost all the performers do. And they enjoy doing these master classes with developing musicians.  

“For all of us volunteers,” Bismillah says, “it’s a thrill to be involved like this, helping the community and getting such wonderful music and dance. Since there’s so much focus on education, the schools and the government have been very involved, too. That’s how we’re able to get this quality of talent here to our little islands.” 

Dickson, whose virtuosity on the sax makes her an international star, not only wowed the audience at the festival, she also coached more than 30 Cayman school kids on their saxophone techniques. And Stringfever, a remarkable string quartet whose instruments are electric and whose approach to classical and contemporary music is like no other group’s, did a special morning talk and concert for 450 students. 


A distinct model  

Structuring a local entertainment industry so that it provides such benefits to both music lovers and youth, and also serves a sophisticated tourist audience during winter months, has brought a distinct model to the attention of smaller markets worldwide.  

“I understand that there are many places that are off the beaten path but want to reach out for world-class performers for their residents and visitors who look at how things happen in the performing arts in Cayman,” Hardie, of Deloitte Cayman, says.  

“Speaking from my own personal perspective, it’s wonderful being on this small island, to be able to enjoy such great music. The Harlem Gospel Choir was very, very popular, a big crowd pleaser and sold-out performance,” she said.  

“And all that’s great. But one of the main reasons Deloitte has been so involved in sponsoring these performances has been the opportunity for the Caymanian children to have real contact with this kind of talent. They may not ordinarily be able to see performers like Amy Dickson, an Emmy nominee, unless they could go to London, New York or Sidney. And these children were able to have access to them free of charge. That’s what’s really special about the festival.” 

Community service: That’s what everyone involved in the nonprofit side of the entertainment business in Cayman talks about. Glen Inanga, deeply involved in the arts scene here and in the arts festival, focuses on that above most else.  

“It makes sense that the laws dictate that work permits are not required for nonprofits,” he says. “There are indeed professional promoters of music events in Cayman that invite performers from overseas to perform in Cayman as a business venture that requires work permits for their visiting artists.” But nonprofit arts groups can pass on their lower costs (from volunteer personnel and their rejection of profits) to audiences. The result: lower ticket prices, sometimes dramatically lower. That helps the groups reach a wider audience, many of whom might not have access to this quality entertainment. 

Naturally, no one asked singer Shaggy to hold hip hop workshops for school kids. His sexually suggestive lyrics prohibit any such thing. But Gidarisingh, who also operates his own entertainment company, Partysurfers Entertainment, said the raucous concert in the midst of Margaritaville’s Mardi Gras Holiday Celebration pulled in more than 2,000 ticket holders, “a good day for business on the waterfront.” 

Those 2,000 represented one stratum of Cayman’s entertainment taste. There are many others.  

For those whose entertainment preferences don’t include Gypsy jazz, classical saxophones, one of the world’s foremost gospel choirs or string quartets (even one playing electric instruments), there are still boxing matches, exposure to the world’s greatest rugby and cricket players and swimming and tennis matches at a sometimes Olympian level. 


Developing local talent  

Another community feature of Cayman’s unusual entertainment industry, according to Bismillah, of the arts festival, is that it tends to encourage the development of local talent. And indeed, there are music schools and participatory athletic programs throughout the islands. 

An economist might consider the temporary work permits required of off-island talent not working through a nonprofit group to be a protectionist policy, keeping the outsiders away from stages and audiences in Cayman. 

But, as Bismillah says, “I can only see this model as bettering our local talent. They get this opportunity to enjoy some of the world’s great artists in more intimate settings and to deal with them one-on-one. It’s a blessing, a Cayman way of sharing.” 


Classical saxophonist Amy Dickson wowed a Cayman Arts Festival audience this year and coached schoolchildren on technique as well.