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Home / Lead Stories / Miss Cayman reaps the rewards

Miss Cayman reaps the rewards


By Ron Shillingford
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The many duties and commitments involved in being Miss Cayman Islands is anything but a hardship for Anika Connolly who almost three months into her tenure, is having a ball. Juggling a day job and fitting in all the functions, events and personal appearances is no hardship at all for the 27-year-old beauty.

“I was once asked which was more difficult, competing for the title or having the title of Miss Cayman,” she said. “And I have to say, competing was more challenging because of how hard we all worked with a huge level of uncertainty in not knowing who would win. Now it is a feeling of euphoria because the hard work has paid off and I get to enjoy the fruits of my labour.”

Since she was crowned, Anika has worked with many local organisations and media personalities and each person she’s encountered has been “amazing to work with or meet.” There have been so many memorable moments so far, she said.

“But if I have to pick my top two, I would say they are the speech I gave at the annual HR Conference put on by the Cayman Islands Society of Human Resource Professionals. I had attended this conference for three years and watched so many notable speakers before me so I almost couldn’t believe it when I had been chosen to be in the speaker line-up this year along with Grace Byers, another successful Caymanian woman.”

The other highlight was Anika’s first official trip with the Department of Tourism to Fort Lauderdale to host the launch of Southwest airlines to the Cayman Islands last month.


She said: “This was my first opportunity to demonstrate Caymankind to people who have never been to Cayman. I think I did a good job and hope that I’ve encouraged more people to visit the Cayman Islands. Not to mention the staff at DoT and Pirates Week are amazing.”

Anika’s itinerary in the coming months is packed full of adventures and new opportunities to be an ambassador for her country. “I’ve started a youth initiative called Youth Rebelution, where I hope to teach teens to rebel against low expectations and will be hosting several events over the next few weeks. Please check out the website for more details youthrebelution.weebly.com

“We also have heard that the next Miss Universe pageant might be happening in November so I will be starting my pageant training soon. This is very exciting and I’m starting to feel butterflies already.”

How does she fit it all in, “That’s the question of the century! It is certainly not easy to fit in a full-time job as well as being an ambassador for my country. But thankfully I have a really good support group that help me stay on top of things.

“My human resources team at CUC have been fully supportive of the time I have to be away and we help each other out. The Miss Cayman Islands committee helps me manage my appearances and takes care of the logistics in the background.

“My sponsors, Renaissance Salon and Edge Athletics make sure that I look my best at all times. My family and friends encourage me and are there for me when I need them.

“And most importantly, I put my trust in God that He will guide me always. I can never say it enough but thank you to everyone who has helped me to get to this point in my life.”


The public’s response to her is generally “excited, happy and elated even” she said and added that her interaction with the public “has got to be by far one of my favourite parts of being Miss Cayman.

“When I meet people they seem so full of energy, and the pride in their eyes moves me to tears sometimes,” she said. “They want to take pictures, ask for my autograph, and for me to talk to their kids or friends.

“It’s amazing how a pageant can bring people together. I even have fans in the Philippines already! They asked me to make a fan sign for them and I had to Google it because I had no idea what that was!”


After winning the contest in March, Anika received a wave of criticism on social media from trolls who thought she didn’t deserve the title. The criticism has died down significantly to the point that she hasn’t heard much.

“And to be honest, I try not to listen to any negative comments made about myself. How can I focus on being my best if I listen to negative critique, I prefer to surround myself with positive people who are going to lift me up and help me reach my goals.”

Six months ago Anika was on a journey to the Miss Cayman title and now she feels she is on a new journey, to do well in the Miss Universe pageant in five months’ time. The Miss Cayman Islands committee and Anika will be reaching out for sponsorship to help her be successful.

She added: “It’s not easy to compete internationally so we hope that individuals and businesses will be willing to come on board and support financially. Cayman has not had a Miss Universe winner yet but if we all come together you never know what we could accomplish. Winning the title would be a dream come true for me, an opportunity to really put Cayman on the map!”

About Ron Shillingford

Ron is a former Cayman based sports editor. He is a best-selling author and novelist, and has worked as a sub-editor on some of the U.K.’s leading national newspapers. He is a certified tutor in English, writing assignments for various publications and websites and ghostwriting memoirs for the London-based publishers Story Terrace. A veteran journalist of more than 30 years standing, Ron’s area of expertise includes sports, human interest and local news reporting.

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