Discover the Local Theater in Cayman

If you’re looking for a unique way to experience Cayman’s local culture, consider catching a show at the island’s community playhouse. The Cayman Drama Society stages several productions each year at the Prospect Playhouse—each one produced and performed by local talent.

This past summer, some of my family and I attended a show while visiting the island, and it was such a fun way to see a different side of Cayman. Before we bought tickets, I checked in with Jenica, the CCC property manager, to get her take on it. She highly recommended it, so we decided to give it a try.

We saw The Ancestors by Lakesha Arei-Angelo, a production that encouraged the audience to participate throughout. Before the curtain rose, we grabbed refreshments from the lobby bar, which is conveniently located just outside the theater doors. The cast included performers of all ages and backgrounds, and they brought so much energy and authenticity to the stage. The narrator, in particular, was absolutely mesmerizing—she carried the story with such beautiful energy and skill. The whole performance felt like a true labor of love, and I even learned a bit of Caribbean history along the way.

After the show, several cast members came out to the lobby, giving us the chance to congratulate them and chat for a few minutes. On the way home, my family and I talked about how happy we were that we got to participate in the local community in this way. We were genuinely delighted with the quality of the production, and we walked away with a piece of Cayman on our hearts.

If you’re visiting soon, Cinderella is now showing at the theater, with tickets available for December 5–7 and 12–14. The synopsis promises plenty of audience participation, silliness, and even chocolate buttons tossed into the crowd—it sounds like a fun one. General admission is $25, and children under 12 are $12. Tickets can be booked here.

If you’re lucky enough to be in Cayman during a show, consider grabbing tickets. It’s a charming, unexpected way to connect with the island beyond the beaches.