For as long as I have been doing this, when people ask what exactly I do, my reply has been: “I am eating my way through the Caribbean.” Half-joke, half-truth, but the reality is that I don’t think there’s a better way to be introduced to a new destination than through its culinary scene, as I have met so many “home grown” geniuses and superstars in my journeys. That’s especially the case when it comes to food festivals, and the Caribbean is downright packed with some outstanding events. 

Hosted by The Ritz-Carlton Grand Cayman, the Cayman Cookout is arguably the best among them, if not based on reputation then at least on the ideology of “all of the above.” During my first visit to the island, I learned that there’s no such thing as a bad dining option. If anything, there are too many good spots — so many that you’ll need multiple visits to experience them all and learn firsthand why Tillies is one of the best beach spots anywhere in the Caribbean. But if you’re looking to vacation here for the first time, there’s no better time than January 14-19, 2026.

Next year’s annual Cayman Cookout features a phenomenal lineup of world-famous culinary talent, beginning with the one and only Emeril Lagasse and the man, myth, legend, and downright living saint José Andrés. They will be joined by (deep breath): Aldo Sohm, Andrew Zimmern, Carla Hall, Charles Joly, Christophe Bellanca, Daniella Soto Innes, EJ Lagasse, Elena Reygadas, Eric Ripert, Gavin Kaysen, Gregory Gourdet, Jeffrey Morgenthaler, Julie Reiner, Kate Gerwin, Lynette Marrero, Madeline Puckette, Michael Kennedy, Ming Tsai, and Stephanie Izard.

Obviously, there are some familiar names from other islands’ events, most notably the Nassau Paradise Island Food and Wine Festival held at Atlantis, which is an absolute blast in itself; however, the Cayman Cookout sets itself apart from any other festival on the planet by offering some of the coolest culinary experiences you can imagine. For example, guests can pay to hop on a private jet and head to Jamaica’s GoldenEye resort — the creative birthplace of James Bond — for a meal and wine pairing with Ripert and Craggy Range founder/owner Terry Peabody. And that’s just a sample of the exclusive action.

When it comes to golf, as I’ve written before, Grand Cayman only has one option, North Sound Golf Club, but it’s among the best in the Caribbean. Guests of the Ritz-Carlton Grand Cayman can book rounds through the hotel before heading off to enjoy the island’s best food from the world’s best chefs.

(Image courtesy of The Ritz-Carlton Grand Cayman/Facebook)