Winston, the Stingray City Ambassador

My first trip out to Stingray City was a huge day of firsts for me—first time on a boat in the ocean, first time petting a stingray, first time holding a starfish, and first time snorkeling. Even on a day full of amazing new experiences, getting to meet Winston, crew member extraordinaire, stands out as one of the highlights.

The first thing that made me smile about Winston was his ability to guess my shoe size just by looking at my feet. He took a quick glance and then handed me a pair of snorkeling fins (which to my surprise weren’t called just “flippers”) that fit on the first try. He laughed and said that people with “little heels and ankles” were by far the hardest people to fit. My shoe store trips would be significantly easier if I had Winston along!

As the boat began to take off towards the Coral Gardens, we were quickly greeted by lots of cold, salty splashes of seawater. Most people squealed and shouted at being suddenly soaked, but Winston opened up his arms, closed his eyes, and smiled as the waves splashed him. “Ahh, you all should enjoy this now because you won’t get any of this on the ride back.” I, like my fellow passengers, was initially a little jarred by the splashes, but seeing Winston enjoy the waves and encourage us to enjoy the experience turned my attitude around.

Since he seemed to have such a positive outlook on being at work, I asked Winston how long he’d been doing boat tours. He’s been working for Stingray City for about eight years. Winston worked in construction for several years after moving to Cayman from Jamaica for better opportunities for his family. I asked which he liked better and with a big smile he said he liked giving tours much better—he gets to be outdoors in a beautiful, laid back atmosphere, and gets to meet lots of people from all around the world. Of all the destinations on the boat tours, he said he enjoys Star Fish Point the most because of the fun but relaxing atmosphere and how much kids enjoy the spot.

Once we arrived at Stingray City, Winston also served as our stingray ambassador. As a few stingrays began to swim by our group, one guest got a little freaked out by the rays being so close. She screamed, flailed, and even tried to escape back onto the boat, but Winston took the time to calm her down. He explained that there was nothing to be afraid of, and slowly guided her over to the stingray. After a few moments, she seemed to calm down a little, and by the time we were finished she even gave the ray a little kiss for luck! As Winston said, “You have to kiss the stingray—it’s seven years good luck!”

All too soon it was time to get back on the boat and leave the stingrays behind, but as I asked Winston if I could give the ray a goodbye pet on the fin, he replied with his signature, “Of course!” Throughout the whole day, any request a guest had—Will you take a photo? Can you explain how starfish eat?—Winston always replied with a cheerful, “Of course!” His kindness and enthusiasm made an already incredible experience even more special.

Whether it was manning the ship’s anchor, explaining how to use snorkel gear, or wrangling stingrays, Winston did everything with a genuine smile and generous spirit. Every time I think back on my big day of firsts, Winston’s smile is a big part of my memories. The first trip won’t be my last time hanging with stingrays for certain, and hopefully it won’t be my last time getting to visit with Winston.